blc-org/A-secret-data-repo huggingface dataset:
Task: reaction
rxn_cls: Esterification
reactants: CCCCCCCCC=CCCCCCCCCOCC(COCCOCCOCCOCCO)OCCCCCCCCC=CCCCCCCCC
CCN=C=NCCCN(C)C
COCCN(CC(=O)OCCN(CC(=O)O)C(=O)OC(C)(C)C)C(=O)OC(C)(C)C
rxn_smiles: CCCCCCCCC=CCCCCCCCCOCC(COCCOCCOCCOCCO)OCCCCCCCCC=CCCCCCCCC.CCN=C=NCCCN(C)C.COCCN(CC(=O)OCCN(CC(=O)O)C(=O)OC(C)(C)C)C(=O)OC(C)(C)C>>CCCCCCCCC=CCCCCCCCCOCC(COCCOCCOCCOCCOC(=O)CN(CCOC(=O)CN(CCOC)C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)OCCCCCCCCC=CCCCCCCCC
Answer: Major Product: CCCCCCCCC=CCCCCCCCCOCC(COCCOCCOCCOCCOC(=O)CN(CCOC(=O)CN(CCOC)C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)OCCCCCCCCC=CCCCCCCCC
Byproduct(s): CCNC(=O)NCCCN(C)C
Task: reaction
rxn_cls: Mitsunobu ester synthesis
reactants: CC(O)C(=O)OCc1ccccc1
CCOC(=O)N=NC(=O)OCC
CN(C(=O)OC(C)(C)C)C(C(=O)O)C(C)(C)C
c1ccc(P(c2ccccc2)c2ccccc2)cc1
rxn_smiles: CC(O)C(=O)OCc1ccccc1.CCOC(=O)N=NC(=O)OCC.CN(C(=O)OC(C)(C)C)C(C(=O)O)C(C)(C)C.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>CC(OC(=O)C(N(C)C(=O)OC(C)(C)C)C(C)(C)C)C(=O)OCc1ccccc1
Answer: Major Product: CC(OC(=O)C(N(C)C(=O)OC(C)(C)C)C(C)(C)C)C(=O)OCc1ccccc1
Byproduct(s): CCOC(=O)NNC(=O)OCCO=P(c1ccccc1)(c1ccccc1)c1ccccc1
Task: reaction
rxn_cls: Bromo Grignard preparation
reactants: Fc1ccc(Br)cc1
reagents: [Mg]
rxn_smiles: Fc1ccc(Br)cc1>[Mg]>Fc1ccc([Mg]Br)cc1
Answer: {"Major Product": "Fc1ccc([Mg]Br)cc1", "Byproduct(s)": []}
Task: reaction
rxn_cls: O-TIPS deprotection
reactants: COCOc1cc(O[Si](C(C)C)(C(C)C)C(C)C)ccc1-c1cc2cnn(C3CC(C)(C)NC(C)(C)C3)c2nn1
reagents: CCCC[N+](CCCC)(CCCC)CCCC
C1CCOC1
[F-]
rxn_smiles: COCOc1cc(O[Si](C(C)C)(C(C)C)C(C)C)ccc1-c1cc2cnn(C3CC(C)(C)NC(C)(C)C3)c2nn1>CCCC[N+](CCCC)(CCCC)CCCC.C1CCOC1.[F-]>COCOc1cc(O)ccc1-c1cc2cnn(C3CC(C)(C)NC(C)(C)C3)c2nn1
Answer: Major Product: COCOc1cc(O)ccc1-c1cc2cnn(C3CC(C)(C)NC(C)(C)C3)c2nn1
Byproduct(s): CC(C)[Si](F)(C(C)C)C(C)C
Task: reaction
rxn_cls: N-Cbz protection
reactants: O=C(Cl)OCc1ccccc1
OCC1Cc2ccccc2CN1
rxn_smiles: O=C(Cl)OCc1ccccc1.OCC1Cc2ccccc2CN1>>O=C(OCc1ccccc1)N1Cc2ccccc2CC1CO
Answer: Major Product: O=C(OCc1ccccc1)N1Cc2ccccc2CC1CO
Byproduct(s): [Cl-]
Task: reaction
rxn_cls: Bechamp reduction
reactants: C=CC(=O)NC1CCN(S(=O)(=O)c2ccc([N+](=O)[O-])cc2)CC1
reagents: [NH4+]
O
[Cl-]
CCO
[Fe]
rxn_smiles: C=CC(=O)NC1CCN(S(=O)(=O)c2ccc([N+](=O)[O-])cc2)CC1>[NH4+].O.[Cl-].CCO.[Fe]>C=CC(=O)NC1CCN(S(=O)(=O)c2ccc(N)cc2)CC1
Answer: Major Product: C=CC(=O)NC1CCN(S(=O)(=O)c2ccc(N)cc2)CC1
Byproduct(s): OO[Fe+2]
Task: reaction
rxn_cls: Bromo N-alkylation
reactants: COC(=O)C(C)(CCBr)c1ccc(Cl)c(Cl)c1
CC(=O)N(C)C1CCNCC1
rxn_smiles: COC(=O)C(C)(CCBr)c1ccc(Cl)c(Cl)c1.CC(=O)N(C)C1CCNCC1>>COC(=O)C(C)(CCN1CCC(N(C)C(C)=O)CC1)c1ccc(Cl)c(Cl)c1
Answer: Major Product: COC(=O)C(C)(CCN1CCC(N(C)C(C)=O)CC1)c1ccc(Cl)c(Cl)c1
Byproduct(s): [Br-]
Task: reaction
rxn_cls: Isocyanate + alcohol reaction
reactants: COC(=O)C(Cc1ccc(OC)c(CO)c1)C(=O)OC
O=C=Nc1ccc(F)cc1F
rxn_smiles: COC(=O)C(Cc1ccc(OC)c(CO)c1)C(=O)OC.O=C=Nc1ccc(F)cc1F>>COC(=O)C(Cc1ccc(OC)c(COC(=O)Nc2ccc(F)cc2F)c1)C(=O)OC
Answer: {"Major Product": "COC(=O)C(Cc1ccc(OC)c(COC(=O)Nc2ccc(F)cc2F)c1)C(=O)OC", "Byproduct(s)": []}
Task: reaction
rxn_cls: Carboxylic ester + amine reaction
reactants: CNC(=O)c1cc(C(=O)Oc2c(Cl)cc(Cl)cc2Cl)cn(Cc2ccccc2)c1=O
CCCN
reagents: CN(C)c1ccncc1
CCN(CC)CC
C1CCOC1
N#N
rxn_smiles: CNC(=O)c1cc(C(=O)Oc2c(Cl)cc(Cl)cc2Cl)cn(Cc2ccccc2)c1=O.CCCN>CN(C)c1ccncc1.CCN(CC)CC.C1CCOC1.N#N>CCCNC(=O)c1cc(C(=O)NC)c(=O)n(Cc2ccccc2)c1
Answer: Major Product: CCCNC(=O)c1cc(C(=O)NC)c(=O)n(Cc2ccccc2)c1
Byproduct(s): [O-]c1c(Cl)cc(Cl)cc1Cl
Task: reaction
rxn_cls: Mitsunobu imide reaction
reactants: CCOC(=O)N=NC(=O)OCC
O=C1NC(=O)c2ccccc21
OC1CC2CCC1C2
c1ccc(P(c2ccccc2)c2ccccc2)cc1
rxn_smiles: CCOC(=O)N=NC(=O)OCC.O=C1NC(=O)c2ccccc21.OC1CC2CCC1C2.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>O=C1c2ccccc2C(=O)N1C1CC2CCC1C2
Answer: Major Product: O=C1c2ccccc2C(=O)N1C1CC2CCC1C2
Byproduct(s): CCOC(=O)NNC(=O)OCCO=P(c1ccccc1)(c1ccccc1)c1ccccc1
Task: reaction
rxn_cls: Carboxy to carbamoyl
reactants: Cc1cc(OCC(=O)O)cc(C)c1Cc1ccc(O)c(C(C)C)c1
CO
N
reagents: O=S(=O)(O)O
ClCCl
CO
CO
O[Na]
rxn_smiles: Cc1cc(OCC(=O)O)cc(C)c1Cc1ccc(O)c(C(C)C)c1.CO.N>O=S(=O)(O)O.ClCCl.CO.CO.O[Na]>Cc1cc(OCC(N)=O)cc(C)c1Cc1ccc(O)c(C(C)C)c1
Answer: Major Product: Cc1cc(OCC(N)=O)cc(C)c1Cc1ccc(O)c(C(C)C)c1
Byproduct(s): [OH-]
Task: reaction
rxn_cls: Claisen-Schmidt condensation
reactants: CC(C)=O
COc1ccc(C=O)cc1
reagents: O=[Zn]
rxn_smiles: CC(C)=O.COc1ccc(C=O)cc1>O=[Zn]>COc1ccc(C=CC(C)=O)cc1
Answer: Major Product: COc1ccc(C=CC(C)=O)cc1
Byproduct(s): [OH-]
Task: reaction
rxn_cls: Amide Schotten-Baumann
reactants: Nc1ccc2c(c1)C(=O)N(C1CCC(=O)NC1=O)C2=O
O=C(Cl)COCCOCCOCCCl
reagents: C1CCOC1
rxn_smiles: Nc1ccc2c(c1)C(=O)N(C1CCC(=O)NC1=O)C2=O.O=C(Cl)COCCOCCOCCCl>C1CCOC1>O=C1CCC(N2C(=O)c3ccc(NC(=O)COCCOCCOCCCl)cc3C2=O)C(=O)N1
Answer: Major Product: O=C1CCC(N2C(=O)c3ccc(NC(=O)COCCOCCOCCCl)cc3C2=O)C(=O)N1
Byproduct(s): [Cl-]
Task: reaction
rxn_cls: Carbamate Schotten-Baumann
reactants: Cc1ccc(-n2nc(C(C)(C)C)cc2N)cc1
O=C(Cl)OCC(Cl)(Cl)Cl
reagents: c1ccncc1
O
rxn_smiles: Cc1ccc(-n2nc(C(C)(C)C)cc2N)cc1.O=C(Cl)OCC(Cl)(Cl)Cl>c1ccncc1.O>Cc1ccc(-n2nc(C(C)(C)C)cc2NC(=O)OCC(Cl)(Cl)Cl)cc1
Answer: Major Product: Cc1ccc(-n2nc(C(C)(C)C)cc2NC(=O)OCC(Cl)(Cl)Cl)cc1
Byproduct(s): [Cl-]
Task: reaction
rxn_cls: Chloro Stille reaction
reactants: C=C(OCC)[Sn](CCCC)(CCCC)CCCC
Cc1nc(N)cc(-c2cc(Cl)cnc2F)n1
reagents: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1
CC(=O)O[Pd]OC(C)=O
C1COCCO1
CN(C)C=O
F[Cs]
rxn_smiles: C=C(OCC)[Sn](CCCC)(CCCC)CCCC.Cc1nc(N)cc(-c2cc(Cl)cnc2F)n1>CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.CC(=O)O[Pd]OC(C)=O.C1COCCO1.CN(C)C=O.F[Cs]>C=C(OCC)c1cnc(F)c(-c2cc(N)nc(C)n2)c1
Answer: Major Product: C=C(OCC)c1cnc(F)c(-c2cc(N)nc(C)n2)c1
Byproduct(s): C=C(OCC)[Sn](Cl)(CCCC)CCCCCCCC[Sn](Cl)(CCCC)CCCCCCCCc1cnc(F)c(-c2cc(N)nc(C)n2)c1
Task: reaction
rxn_cls: Mesyloxy N-alkylation
reactants: CS(=O)(=O)OCc1ncc(-c2ccc(F)cc2)o1
N#Cc1ccc(NCC(F)(F)F)cc1C(F)(F)F
reagents: O=C(O[Cs])O[Cs]
rxn_smiles: CS(=O)(=O)OCc1ncc(-c2ccc(F)cc2)o1.N#Cc1ccc(NCC(F)(F)F)cc1C(F)(F)F>O=C(O[Cs])O[Cs]>N#Cc1ccc(N(Cc2ncc(-c3ccc(F)cc3)o2)CC(F)(F)F)cc1C(F)(F)F
Answer: Major Product: N#Cc1ccc(N(Cc2ncc(-c3ccc(F)cc3)o2)CC(F)(F)F)cc1C(F)(F)F
Byproduct(s): CS(=O)(=O)[O-]
Task: reaction
rxn_cls: Methoxy to hydroxy
reactants: COc1cccc2c1Sc1ccccc1CC2
reagents: O
Cl
c1ccncc1
rxn_smiles: COc1cccc2c1Sc1ccccc1CC2>O.Cl.c1ccncc1>Oc1cccc2c1Sc1ccccc1CC2
Answer: Major Product: Oc1cccc2c1Sc1ccccc1CC2
Byproduct(s): CCl
Task: reaction
rxn_cls: Knoevenagel condensation
reactants: CC(=O)Nc1ccc(C=O)cc1
N#CCC#N
reagents: CCO
C1CCNCC1
rxn_smiles: CC(=O)Nc1ccc(C=O)cc1.N#CCC#N>CCO.C1CCNCC1>CC(=O)Nc1ccc(C=C(C#N)C#N)cc1
Answer: Major Product: CC(=O)Nc1ccc(C=C(C#N)C#N)cc1
Byproduct(s): [OH-]
Task: reaction
rxn_cls: Ester to alcohol reduction
reactants: COC(=O)C(C)(C)C(c1nc(Cl)cs1)c1[nH]c(-c2ccccc2)c2c(=O)n(C)c(=O)n(C)c12
reagents: [Na+]
CO
[Li]Cl
[BH4-]
rxn_smiles: COC(=O)C(C)(C)C(c1nc(Cl)cs1)c1[nH]c(-c2ccccc2)c2c(=O)n(C)c(=O)n(C)c12>[Na+].CO.[Li]Cl.[BH4-]>Cn1c(=O)c2c(-c3ccccc3)[nH]c(C(c3nc(Cl)cs3)C(C)(C)CO)c2n(C)c1=O
Answer: Major Product: Cn1c(=O)c2c(-c3ccccc3)[nH]c(C(c3nc(Cl)cs3)C(C)(C)CO)c2n(C)c1=O
Byproduct(s): BCO
Task: reaction
rxn_cls: Wittig olefination
reactants: CCCCCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1
COC(=O)CCCCCCC=O
rxn_smiles: CCCCCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.COC(=O)CCCCCCC=O>>CCCCCC=CCCCCCCC(=O)OC
Answer: Major Product: CCCCCC=CCCCCCCC(=O)OC
Byproduct(s): O=P(c1ccccc1)(c1ccccc1)c1ccccc1
Task: reaction
rxn_cls: Steglich esterification
reactants: C(=NC1CCCCC1)=NC1CCCCC1
CCCCCCCCCCCCCCCCCC(=O)OCC(CCCC(=O)O)COC(=O)C(NC(c1ccccc1)(c1ccccc1)c1ccccc1)C(C)C
Nc1nc2c(ncn2C2CC(F)C(CO)O2)c(=O)[nH]1
rxn_smiles: C(=NC1CCCCC1)=NC1CCCCC1.CCCCCCCCCCCCCCCCCC(=O)OCC(CCCC(=O)O)COC(=O)C(NC(c1ccccc1)(c1ccccc1)c1ccccc1)C(C)C.Nc1nc2c(ncn2C2CC(F)C(CO)O2)c(=O)[nH]1>>CCCCCCCCCCCCCCCCCC(=O)OCC(CCCC(=O)OCC1OC(n2cnc3c(=O)[nH]c(N)nc32)CC1F)COC(=O)C(NC(c1ccccc1)(c1ccccc1)c1ccccc1)C(C)C
Answer: Major Product: CCCCCCCCCCCCCCCCCC(=O)OCC(CCCC(=O)OCC1OC(n2cnc3c(=O)[nH]c(N)nc32)CC1F)COC(=O)C(NC(c1ccccc1)(c1ccccc1)c1ccccc1)C(C)C
Byproduct(s): O=C(NC1CCCCC1)NC1CCCCC1
Task: reaction
rxn_cls: Aldehyde reductive amination
reactants: Cc1c(NC(=O)c2ccc(OCC3CCCO3)cc2)ccc2cc(C=O)cnc12
NCC1CC1
reagents: CC(=O)O[BH-](OC(C)=O)OC(C)=O
CN1CCCC1=O
CC(=O)O
O[Na]
O
[Na+]
rxn_smiles: Cc1c(NC(=O)c2ccc(OCC3CCCO3)cc2)ccc2cc(C=O)cnc12.NCC1CC1>CC(=O)O[BH-](OC(C)=O)OC(C)=O.CN1CCCC1=O.CC(=O)O.O[Na].O.[Na+]>Cc1c(NC(=O)c2ccc(OCC3CCCO3)cc2)ccc2cc(CNCC3CC3)cnc12
Answer: Major Product: Cc1c(NC(=O)c2ccc(OCC3CCCO3)cc2)ccc2cc(CNCC3CC3)cnc12
Byproduct(s): CC(=O)OB(OC(C)=O)OC(C)=OO
Task: reaction
rxn_cls: Chloro N-alkylation
reactants: CC(Nc1nccc(N2C(=O)OCC2C(C)C)n1)c1ccc(CCl)cc1
c1cn2c(n1)CNCC2
rxn_smiles: CC(Nc1nccc(N2C(=O)OCC2C(C)C)n1)c1ccc(CCl)cc1.c1cn2c(n1)CNCC2>>CC(Nc1nccc(N2C(=O)OCC2C(C)C)n1)c1ccc(CN2CCn3ccnc3C2)cc1
Answer: Major Product: CC(Nc1nccc(N2C(=O)OCC2C(C)C)n1)c1ccc(CN2CCn3ccnc3C2)cc1
Byproduct(s): [Cl-]
Task: reaction
rxn_cls: Chloro Grignard reaction
reactants: C[Mg]Cl
O=C1CCCc2c1[nH]c1cc(Cl)c(Cl)cc21
reagents: C1CCOC1
rxn_smiles: C[Mg]Cl.O=C1CCCc2c1[nH]c1cc(Cl)c(Cl)cc21>C1CCOC1>CC1(O)CCCc2c1[nH]c1cc(Cl)c(Cl)cc21
Answer: Major Product: CC1(O)CCCc2c1[nH]c1cc(Cl)c(Cl)cc21
Byproduct(s): [Mg+]Cl
Task: reaction
rxn_cls: Williamson ether synthesis
reactants: COC(=O)c1nn(-c2c(Cl)cc(C(F)(F)F)cc2Cl)c(O)c1SC(F)(F)F
CCOS(=O)(=O)OCC
reagents: C1COCCO1
[NaH]
rxn_smiles: COC(=O)c1nn(-c2c(Cl)cc(C(F)(F)F)cc2Cl)c(O)c1SC(F)(F)F.CCOS(=O)(=O)OCC>C1COCCO1.[NaH]>CCOc1c(SC(F)(F)F)c(C(=O)OC)nn1-c1c(Cl)cc(C(F)(F)F)cc1Cl
Answer: Major Product: CCOc1c(SC(F)(F)F)c(C(=O)OC)nn1-c1c(Cl)cc(C(F)(F)F)cc1Cl
Byproduct(s): CCOS(=O)(=O)O[Cl-][Cl-][H]C(Cl)(Cl)[OH]S(=O)(=O)OCC[H]C(Cl)[OH]S(=O)(=O)OCC
Task: reaction
rxn_cls: Iodo Buchwald-Hartwig amination
reactants: CN1CCCC1COc1nc2c(c(N3CCN(C(=O)OCc4ccccc4)CC3CC#N)n1)CCNC2
Ic1cccc2ccccc12
Nc1ccccc1-c1[c-]cccc1
O=C(O[Cs])O[Cs]
[Pd]
rxn_smiles: CN1CCCC1COc1nc2c(c(N3CCN(C(=O)OCc4ccccc4)CC3CC#N)n1)CCNC2.Ic1cccc2ccccc12.Nc1ccccc1-c1[c-]cccc1.O=C(O[Cs])O[Cs].[Pd]>>CN1CCCC1COc1nc2c(c(N3CCN(C(=O)OCc4ccccc4)CC3CC#N)n1)CCN(c1cccc3ccccc13)C2
Answer: Major Product: CN1CCCC1COc1nc2c(c(N3CCN(C(=O)OCc4ccccc4)CC3CC#N)n1)CCN(c1cccc3ccccc13)C2
Byproduct(s): O=C(O)O[Cs][Cs+][I-][c-]1ccccc1-c1ccccc1Nc1cccc2ccccc12
Task: reaction
rxn_cls: Iodo Suzuki coupling
reactants: Ic1cc(-n2c3ccccc3c3ccccc32)cc2c1Oc1ccccc1[Si]2(c1ccccc1)c1ccccc1
CC1(C)c2ccccc2Oc2c(B(O)O)cccc21
reagents: c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1
Cc1ccccc1
O=C(O[K])O[K]
CCO
O
rxn_smiles: Ic1cc(-n2c3ccccc3c3ccccc32)cc2c1Oc1ccccc1[Si]2(c1ccccc1)c1ccccc1.CC1(C)c2ccccc2Oc2c(B(O)O)cccc21>c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1.Cc1ccccc1.O=C(O[K])O[K].CCO.O>CC1(C)c2ccccc2Oc2c(-c3cc(-n4c5ccccc5c5ccccc54)cc4c3Oc3ccccc3[Si]4(c3ccccc3)c3ccccc3)cccc21
Answer: Major Product: CC1(C)c2ccccc2Oc2c(-c3cc(-n4c5ccccc5c5ccccc54)cc4c3Oc3ccccc3[Si]4(c3ccccc3)c3ccccc3)cccc21
Byproduct(s): CCOB(O)OO=C(O[K])OB(O)OOB(O)O[I-][K+]c1ccc(P(c2ccccc2)c2ccccc2)cc1c1ccc(P(c2ccccc2)c2ccccc2)cc1
Task: reaction
rxn_cls: N-Boc protection
reactants: CC(C)(C)OC(=O)OC(=O)OC(C)(C)C
NCCN
reagents: ClCCl
rxn_smiles: CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.NCCN>ClCCl>CC(C)(C)OC(=O)NCCN
Answer: Major Product: CC(C)(C)OC(=O)NCCN
Byproduct(s): CC(C)(C)OO=C=O
Task: reaction
rxn_cls: N-Boc deprotection
reactants: CC(C)(C)OC(=O)N1C2CC(Oc3ccc(-c4ccc(-n5ccc(F)n5)c5ncsc45)nn3)CC1C(F)(F)C2
reagents: CO
rxn_smiles: CC(C)(C)OC(=O)N1C2CC(Oc3ccc(-c4ccc(-n5ccc(F)n5)c5ncsc45)nn3)CC1C(F)(F)C2>CO>Fc1ccn(-c2ccc(-c3ccc(OC4CC5CC(F)(F)C(C4)N5)nn3)c3scnc23)n1
Answer: Major Product: Fc1ccn(-c2ccc(-c3ccc(OC4CC5CC(F)(F)C(C4)N5)nn3)c3scnc23)n1
Byproduct(s): C[C+](C)CO=C=O
Task: reaction
rxn_cls: Olefin metathesis
reactants: CN(C)c1ccc(C=Cc2ccc(S(=O)(=O)CCCO)cc2)cc1
O=S(=O)(CCCOC1CCCOC1)c1ccc(C=Cc2ccc3c(c2)OCCO3)cc1
rxn_smiles: CN(C)c1ccc(C=Cc2ccc(S(=O)(=O)CCCO)cc2)cc1.O=S(=O)(CCCOC1CCCOC1)c1ccc(C=Cc2ccc3c(c2)OCCO3)cc1>>O=S(=O)(CCCO)c1ccc(C=Cc2ccc3c(c2)OCCO3)cc1
Answer: {"Major Product": "O=S(=O)(CCCO)c1ccc(C=Cc2ccc3c(c2)OCCO3)cc1", "Byproduct(s)": []}
Task: reaction
rxn_cls: Ritter reaction
reactants: CC(C)(C)NS(=O)(=O)c1ccc(C#N)o1
reagents: O=C(O)C(F)(F)F
rxn_smiles: CC(C)(C)NS(=O)(=O)c1ccc(C#N)o1>O=C(O)C(F)(F)F>CC(C)(C)NC(=O)c1ccc(S(N)(=O)=O)o1
Answer: {"Major Product": "CC(C)(C)NC(=O)c1ccc(S(N)(=O)=O)o1", "Byproduct(s)": []}
Task: reaction
rxn_cls: Passerini reaction
reactants: CC(C)(C)OC(=O)N[C@H](C=O)CC1CCC1
[C-]#[N+]C1CC1
CC(=O)O
reagents: CCOC(C)=O
ClCCl
rxn_smiles: CC(C)(C)OC(=O)N[C@H](C=O)CC1CCC1.[C-]#[N+]C1CC1.CC(=O)O>CCOC(C)=O.ClCCl>CC(=O)OC(C(=O)NC1CC1)[C@H](CC1CCC1)NC(=O)OC(C)(C)C
Answer: {"Major Product": "CC(=O)OC(C(=O)NC1CC1)[C@H](CC1CCC1)NC(=O)OC(C)(C)C", "Byproduct(s)": []}
Task: reaction
rxn_cls: Carboxylic acid + hydrazine condensation
reactants: CC(C)(C)OC(=O)COc1ccc(C(=O)O)cc1OCC(=O)OC(C)(C)C
NNC(=O)OCc1ccccc1
reagents: CCN=C=NCCCN(C)C
On1nnc2ccccc21
CCN(C(C)C)C(C)C
CN(C)C=O
Cl
rxn_smiles: CC(C)(C)OC(=O)COc1ccc(C(=O)O)cc1OCC(=O)OC(C)(C)C.NNC(=O)OCc1ccccc1>CCN=C=NCCCN(C)C.On1nnc2ccccc21.CCN(C(C)C)C(C)C.CN(C)C=O.Cl>CC(C)(C)OC(=O)COc1ccc(C(=O)NNC(=O)OCc2ccccc2)cc1OCC(=O)OC(C)(C)C
Answer: {"Major Product": "CC(C)(C)OC(=O)COc1ccc(C(=O)NNC(=O)OCc2ccccc2)cc1OCC(=O)OC(C)(C)C", "Byproduct(s)": []}
Task: reaction
rxn_cls: Knorr pyrazole synthesis
reactants: CCOC(=O)C(=O)CC(=O)CCN1C(=O)c2ccccc2C1=O
CCNN
O=C(O)C(=O)O
[Na]
reagents: CCOCC
CC(=O)O
rxn_smiles: CCOC(=O)C(=O)CC(=O)CCN1C(=O)c2ccccc2C1=O.CCNN.O=C(O)C(=O)O.[Na]>CCOCC.CC(=O)O>CCOC(=O)c1cc(CCN2C(=O)c3ccccc3C2=O)n(CC)n1
Answer: {"Major Product": "CCOC(=O)c1cc(CCN2C(=O)c3ccccc3C2=O)n(CC)n1", "Byproduct(s)": []}
Task: reaction
rxn_cls: Ugi reaction
reactants: [C-]#[N+]C1CCCCC1
CC(=O)Cl
CC=O
Nc1ncccn1
reagents: O=Cl(=O)(=O)O
rxn_smiles: [C-]#[N+]C1CCCCC1.CC(=O)Cl.CC=O.Nc1ncccn1>O=Cl(=O)(=O)O>[Cl-].CC(=O)[n+]1c(C)c(NC2CCCCC2)n2cccnc21
Answer: {"Major Product": "[Cl-]CC(=O)[n+]1c(C)c(NC2CCCCC2)n2cccnc21", "Byproduct(s)": []}
Task: reaction
rxn_cls: Staudinger reduction
reactants: CC(C)(C)OC(=O)N1C[C@H](Sc2ccc(Cl)cn2)[C@@](O)(CN=[N+]=[N-])C1
reagents: C1CCOC1
CP(C)C
[C-]#[O+]
O
rxn_smiles: CC(C)(C)OC(=O)N1C[C@H](Sc2ccc(Cl)cn2)[C@@](O)(CN=[N+]=[N-])C1>C1CCOC1.CP(C)C.[C-]#[O+].O>CC(C)(C)OC(=O)N1C[C@H](Sc2ccc(Cl)cn2)[C@@](O)(CN)C1
Answer: {"Major Product": "CC(C)(C)OC(=O)N1C[C@H](Sc2ccc(Cl)cn2)[C@@](O)(CN)C1", "Byproduct(s)": []}
Task: reaction
rxn_cls: Transesterification
reactants: COC(=O)C(O)(c1cccc(Cl)c1)c1cccc(Cl)c1
CN1[C@@H]2CC=C[C@@]1(O)CC2
reagents: O
CC#N
[Na]
rxn_smiles: COC(=O)C(O)(c1cccc(Cl)c1)c1cccc(Cl)c1.CN1[C@@H]2CC=C[C@@]1(O)CC2>O.CC#N.[Na]>CN1[C@@H]2CC=C[C@@]1(OC(=O)C(O)(c1cccc(Cl)c1)c1cccc(Cl)c1)CC2
Answer: {"Major Product": "CN1[C@@H]2CC=C[C@@]1(OC(=O)C(O)(c1cccc(Cl)c1)c1cccc(Cl)c1)CC2", "Byproduct(s)": []}
Task: reaction
rxn_cls: Ketone Hosomi-Sakurai reaction
reactants: CCOC(=O)C(=O)c1ccccc1
C=CC[Si](C)(C)C
reagents: Cl[Sn](Cl)(Cl)Cl
ClCCl
rxn_smiles: CCOC(=O)C(=O)c1ccccc1.C=CC[Si](C)(C)C>Cl[Sn](Cl)(Cl)Cl.ClCCl>C=CCC(O)(C(=O)OCC)c1ccccc1
Answer: {"Major Product": "C=CCC(O)(C(=O)OCC)c1ccccc1", "Byproduct(s)": []}
Task: reaction
rxn_cls: Eschweiler-Clarke methylation
reactants: C=O
COC(=O)c1ccc2c(c1)CNC2
reagents: O=CO
rxn_smiles: C=O.COC(=O)c1ccc2c(c1)CNC2>O=CO>COC(=O)c1ccc2c(c1)CN(C)C2
Answer: {"Major Product": "COC(=O)c1ccc2c(c1)CN(C)C2", "Byproduct(s)": []}
Task: reaction
rxn_cls: Hydroxy to triflyloxy
reactants: COc1cccc(C2(c3ccc(O)cc3)CCCN(Cc3ccccc3)C2)c1
O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F
reagents: c1ccncc1
O=C(O)O[Na]
ClCCl
O
rxn_smiles: COc1cccc(C2(c3ccc(O)cc3)CCCN(Cc3ccccc3)C2)c1.O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F>c1ccncc1.O=C(O)O[Na].ClCCl.O>COc1cccc(C2(c3ccc(OS(=O)(=O)C(F)(F)F)cc3)CCCN(Cc3ccccc3)C2)c1
Answer: {"Major Product": "COc1cccc(C2(c3ccc(OS(=O)(=O)C(F)(F)F)cc3)CCCN(Cc3ccccc3)C2)c1", "Byproduct(s)": []}
Task: reaction
rxn_cls: Alkene Ritter reaction
reactants: O
C=CC#N
C=C(C)C
reagents: COC
O=S(=O)(O)O
Oc1ccc(O)cc1
rxn_smiles: O.C=CC#N.C=C(C)C>COC.O=S(=O)(O)O.Oc1ccc(O)cc1>C=CC(=O)NC(C)(C)C
Answer: {"Major Product": "C=CC(=O)NC(C)(C)C", "Byproduct(s)": []}
Task: reaction
rxn_cls: Triflyloxy Suzuki coupling
reactants: CC(C)(C)OC(=O)N1C[C@H]2CC(OS(=O)(=O)C(F)(F)F)=C[C@H]2C1
CC1(C)OB(c2ccc(Oc3ncccn3)cc2)OC1(C)C
reagents: c1ccc(P(c2ccccc2)(c2ccccc2)[Pd](P(c2ccccc2)(c2ccccc2)c2ccccc2)(P(c2ccccc2)(c2ccccc2)c2ccccc2)P(c2ccccc2)(c2ccccc2)c2ccccc2)cc1
O=C(O[Na])O[Na]
C1COCCO1
O
rxn_smiles: CC(C)(C)OC(=O)N1C[C@H]2CC(OS(=O)(=O)C(F)(F)F)=C[C@H]2C1.CC1(C)OB(c2ccc(Oc3ncccn3)cc2)OC1(C)C>c1ccc(P(c2ccccc2)(c2ccccc2)[Pd](P(c2ccccc2)(c2ccccc2)c2ccccc2)(P(c2ccccc2)(c2ccccc2)c2ccccc2)P(c2ccccc2)(c2ccccc2)c2ccccc2)cc1.O=C(O[Na])O[Na].C1COCCO1.O>CC(C)(C)OC(=O)N1C[C@H]2CC(c3ccc(Oc4ncccn4)cc3)=C[C@H]2C1
Answer: {"Major Product": "CC(C)(C)OC(=O)N1C[C@H]2CC(c3ccc(Oc4ncccn4)cc3)=C[C@H]2C1", "Byproduct(s)": []}
Task: reaction
rxn_cls: Sulfide + amine reaction
reactants: CCCSC(SCCC)=C(C#N)C#N
C1CCNC1
reagents: CCCSC(=C(C#N)C#N)N1CCOCC1
CCO
rxn_smiles: CCCSC(SCCC)=C(C#N)C#N.C1CCNC1>CCCSC(=C(C#N)C#N)N1CCOCC1.CCO>CCCSC(=C(C#N)C#N)N1CCCC1
Answer: {"Major Product": "CCCSC(=C(C#N)C#N)N1CCCC1", "Byproduct(s)": []}
Task: reaction
rxn_cls: Carboxylic acid + thioamide condensation
reactants: CC(=NNC(N)=S)C(=O)O
reagents: O
O=C(O[Na])O[Na]
rxn_smiles: CC(=NNC(N)=S)C(=O)O>O.O=C(O[Na])O[Na]>Cc1n[nH]c(=S)[nH]c1=O
Answer: {"Major Product": "Cc1n[nH]c(=S)[nH]c1=O", "Byproduct(s)": []}