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@skearnes

skearnes/reaction.pbtxt Secret

Created Jan 9, 2021
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identifiers {
type: NAME
value: "deoxyfluorination"
}
inputs {
key: "alcohol in THF"
value {
components {
identifiers {
type: SMILES
value: "C"
}
amount {
moles {
value: 0.1
units: MILLIMOLE
}
}
reaction_role: REACTANT
is_limiting: true
}
components {
identifiers {
type: SMILES
value: "C1CCOC1"
}
amount {
volume {
value: 125.0
units: MICROLITER
}
volume_includes_solutes: true
}
reaction_role: SOLVENT
preparations {
type: DRIED
}
}
addition_order: 1
}
}
inputs {
key: "base"
value {
components {
identifiers {
type: SMILES
value: "C"
}
amount {
moles {
value: 0.15
units: MILLIMOLE
}
}
reaction_role: REAGENT
}
addition_order: 3
}
}
inputs {
key: "sulfonyl fluoride solution"
value {
components {
identifiers {
type: SMILES
value: "C"
}
amount {
moles {
value: 0.11
units: MILLIMOLE
}
}
reaction_role: REACTANT
is_limiting: false
}
components {
identifiers {
type: SMILES
value: "C1CCOC1"
}
amount {
volume {
value: 125.0
units: MICROLITER
}
volume_includes_solutes: true
}
reaction_role: SOLVENT
preparations {
type: DRIED
}
}
addition_order: 2
}
}
setup {
vessel {
type {
type: VIAL
}
material {
type: GLASS
}
attachments {
type: CAP
}
volume {
value: 1.0
units: MILLILITER
}
}
is_automated: false
}
conditions {
temperature {
control {
type: AMBIENT
}
}
pressure {
control {
type: SEALED
}
atmosphere {
type: AIR
}
}
stirring {
method {
type: STIR_BAR
}
rate {
type: HIGH
details: "600"
}
}
}
workups {
type: ADDITION
input {
components {
identifiers {
type: NAME
value: "1-fluoronaphthalene"
}
identifiers {
type: SMILES
value: "C1=CC=C2C(=C1)C=CC=C2F"
}
amount {
moles {
value: 0.1
units: MILLIMOLE
}
}
reaction_role: INTERNAL_STANDARD
}
components {
identifiers {
type: NAME
value: "CDCl3"
}
identifiers {
type: SMILES
value: "[2H]C(Cl)(Cl)Cl"
}
amount {
volume {
value: 250.0
units: MICROLITER
}
volume_includes_solutes: true
}
reaction_role: WORKUP
}
}
}
outcomes {
reaction_time {
value: 48.0
units: HOUR
}
products {
identifiers {
type: SMILES
value: "C"
}
is_desired_product: true
measurements {
analysis_key: "19f NMR of crude"
type: YIELD
uses_internal_standard: true
percentage {
value: 50.0
precision: 4.8
}
}
measurements {
analysis_key: "19f NMR of crude"
type: IDENTITY
uses_internal_standard: true
}
reaction_role: PRODUCT
}
analyses {
key: "19f NMR of crude"
value {
type: NMR_OTHER
details: "19F NMR using 1 equiv 1-fluoronaphthalene in chloroform as internal standard"
is_of_isolated_species: false
instrument_manufacturer: "Bruker"
}
}
}
provenance {
city: "Princeton, NJ"
doi: "10.1021/jacs.8b01523"
publication_url: "https://pubs.acs.org/doi/10.1021/jacs.8b01523"
record_created {
time {
value: "8/8/2020, 3:01:25 PM"
}
person {
name: "Connor W. Coley"
orcid: "0000-0002-8271-8723"
organization: "MIT"
email: "ccoley@mit.edu"
}
}
}
identifiers {
type: NAME
value: "deoxyfluorination"
}
inputs {
key: "alcohol in THF"
value {
components {
identifiers {
type: SMILES
value: "$alcohol_smiles$"
}
amount {
moles {
value: 0.1
units: MILLIMOLE
}
}
reaction_role: REACTANT
is_limiting: true
}
components {
identifiers {
type: SMILES
value: "C1CCOC1"
}
amount {
volume {
value: 125.0
units: MICROLITER
}
volume_includes_solutes: true
}
reaction_role: SOLVENT
preparations {
type: DRIED
}
}
addition_order: 1
}
}
inputs {
key: "base"
value {
components {
identifiers {
type: SMILES
value: "$base_smiles$"
}
amount {
moles {
value: 0.15
units: MILLIMOLE
}
}
reaction_role: REAGENT
}
addition_order: 3
}
}
inputs {
key: "sulfonyl fluoride solution"
value {
components {
identifiers {
type: SMILES
value: "$sulfonyl_fluoride_smiles$"
}
amount {
moles {
value: 0.11
units: MILLIMOLE
}
}
reaction_role: REACTANT
is_limiting: false
}
components {
identifiers {
type: SMILES
value: "C1CCOC1"
}
amount {
volume {
value: 125.0
units: MICROLITER
}
volume_includes_solutes: true
}
reaction_role: SOLVENT
preparations {
type: DRIED
}
}
addition_order: 2
}
}
setup {
vessel {
type {
type: VIAL
}
material {
type: GLASS
}
attachments {
type: CAP
}
volume {
value: 1.0
units: MILLILITER
}
}
is_automated: false
}
conditions {
temperature {
control {
type: AMBIENT
}
}
pressure {
control {
type: SEALED
}
atmosphere {
type: AIR
}
}
stirring {
method {
type: STIR_BAR
}
rate {
type: HIGH
details: "600"
}
}
}
workups {
type: ADDITION
input {
components {
identifiers {
type: NAME
value: "1-fluoronaphthalene"
}
identifiers {
type: SMILES
value: "C1=CC=C2C(=C1)C=CC=C2F"
}
amount {
moles {
value: 0.1
units: MILLIMOLE
}
}
reaction_role: INTERNAL_STANDARD
}
components {
identifiers {
type: NAME
value: "CDCl3"
}
identifiers {
type: SMILES
value: "[2H]C(Cl)(Cl)Cl"
}
amount {
volume {
value: 250.0
units: MICROLITER
}
volume_includes_solutes: true
}
reaction_role: WORKUP
}
}
}
outcomes {
reaction_time {
value: 48.0
units: HOUR
}
products {
identifiers {
type: SMILES
value: "$product_smiles$"
}
is_desired_product: true
measurements {
analysis_key: "19f NMR of crude"
type: YIELD
uses_internal_standard: true
percentage {
value: $product_yield$
precision: 4.8
}
}
measurements {
analysis_key: "19f NMR of crude"
type: IDENTITY
uses_internal_standard: true
}
reaction_role: PRODUCT
}
analyses {
key: "19f NMR of crude"
value {
type: NMR_OTHER
details: "19F NMR using 1 equiv 1-fluoronaphthalene in chloroform as internal standard"
is_of_isolated_species: false
instrument_manufacturer: "Bruker"
}
}
}
provenance {
city: "Princeton, NJ"
doi: "10.1021/jacs.8b01523"
publication_url: "https://pubs.acs.org/doi/10.1021/jacs.8b01523"
record_created {
time {
value: "8/8/2020, 3:01:25 PM"
}
person {
name: "Connor W. Coley"
orcid: "0000-0002-8271-8723"
organization: "MIT"
email: "ccoley@mit.edu"
}
}
}
alcohol_smiles sulfonyl_fluoride_smiles base_smiles product_smiles product_yield
c1ccccc1CCC(O)C Clc1ccc(S(=O)(=O)F)cc1 N\2=C1\N(CCCCC1)CCC/2 c1ccccc1CCC(F)C 40
c1ccccc1CCC(O)C Clc1ccc(S(=O)(=O)F)cc1 CN1CCCN2C1=NCCC2 c1ccccc1CCC(F)C 54
c1ccccc1CCC(O)C Clc1ccc(S(=O)(=O)F)cc1 CC(C)(C)N=C(N(C)C)N(C)C c1ccccc1CCC(F)C 41
c1ccccc1CCC(O)C Clc1ccc(S(=O)(=O)F)cc1 CC(C)(C)N=P(N1CCCC1)(N2CCCC2)N3CCCC3 c1ccccc1CCC(F)C 42
c1ccccc1CCC(O)C O=S(C1=CC=CC=N1)(F)=O N\2=C1\N(CCCCC1)CCC/2 c1ccccc1CCC(F)C 57
c1ccccc1CCC(O)C O=S(C1=CC=CC=N1)(F)=O CN1CCCN2C1=NCCC2 c1ccccc1CCC(F)C 59
c1ccccc1CCC(O)C O=S(C1=CC=CC=N1)(F)=O CC(C)(C)N=C(N(C)C)N(C)C c1ccccc1CCC(F)C 49
c1ccccc1CCC(O)C O=S(C1=CC=CC=N1)(F)=O CC(C)(C)N=P(N1CCCC1)(N2CCCC2)N3CCCC3 c1ccccc1CCC(F)C 53
c1ccccc1CCC(O)C O=S(C1=CC=C(C(F)(F)F)C=C1)(F)=O N\2=C1\N(CCCCC1)CCC/2 c1ccccc1CCC(F)C 52
c1ccccc1CCC(O)C O=S(C1=CC=C(C(F)(F)F)C=C1)(F)=O CN1CCCN2C1=NCCC2 c1ccccc1CCC(F)C 69
c1ccccc1CCC(O)C O=S(C1=CC=C(C(F)(F)F)C=C1)(F)=O CC(C)(C)N=C(N(C)C)N(C)C c1ccccc1CCC(F)C 57
c1ccccc1CCC(O)C O=S(C1=CC=C(C(F)(F)F)C=C1)(F)=O CC(C)(C)N=P(N1CCCC1)(N2CCCC2)N3CCCC3 c1ccccc1CCC(F)C 60
c1ccccc1CCC(O)C O=S(C1=CC=C([N+]([O-])=O)C=C1)(F)=O N\2=C1\N(CCCCC1)CCC/2 c1ccccc1CCC(F)C 54
c1ccccc1CCC(O)C O=S(C1=CC=C([N+]([O-])=O)C=C1)(F)=O CN1CCCN2C1=NCCC2 c1ccccc1CCC(F)C 63
c1ccccc1CCC(O)C O=S(C1=CC=C([N+]([O-])=O)C=C1)(F)=O CC(C)(C)N=C(N(C)C)N(C)C c1ccccc1CCC(F)C 55
c1ccccc1CCC(O)C O=S(C1=CC=C([N+]([O-])=O)C=C1)(F)=O CC(C)(C)N=P(N1CCCC1)(N2CCCC2)N3CCCC3 c1ccccc1CCC(F)C 51
c1ccccc1CCC(O)C C(C(C(F)(F)S(=O)(=O)F)(F)F)(C(F)(F)F)(F)F N\2=C1\N(CCCCC1)CCC/2 c1ccccc1CCC(F)C 39
c1ccccc1CCC(O)C C(C(C(F)(F)S(=O)(=O)F)(F)F)(C(F)(F)F)(F)F CN1CCCN2C1=NCCC2 c1ccccc1CCC(F)C 60
c1ccccc1CCC(O)C C(C(C(F)(F)S(=O)(=O)F)(F)F)(C(F)(F)F)(F)F CC(C)(C)N=C(N(C)C)N(C)C c1ccccc1CCC(F)C 61
c1ccccc1CCC(O)C C(C(C(F)(F)S(=O)(=O)F)(F)F)(C(F)(F)F)(F)F CC(C)(C)N=P(N1CCCC1)(N2CCCC2)N3CCCC3 c1ccccc1CCC(F)C 65
c1ccccc1-c2ccc(CO)cc2 Clc1ccc(S(=O)(=O)F)cc1 N\2=C1\N(CCCCC1)CCC/2 c1ccccc1-c2ccc(CF)cc2 11
c1ccccc1-c2ccc(CO)cc2 Clc1ccc(S(=O)(=O)F)cc1 CN1CCCN2C1=NCCC2 c1ccccc1-c2ccc(CF)cc2 36
c1ccccc1-c2ccc(CO)cc2 Clc1ccc(S(=O)(=O)F)cc1 CC(C)(C)N=C(N(C)C)N(C)C c1ccccc1-c2ccc(CF)cc2 83
c1ccccc1-c2ccc(CO)cc2 Clc1ccc(S(=O)(=O)F)cc1 CC(C)(C)N=P(N1CCCC1)(N2CCCC2)N3CCCC3 c1ccccc1-c2ccc(CF)cc2 92
c1ccccc1-c2ccc(CO)cc2 O=S(C1=CC=CC=N1)(F)=O N\2=C1\N(CCCCC1)CCC/2 c1ccccc1-c2ccc(CF)cc2 12
c1ccccc1-c2ccc(CO)cc2 O=S(C1=CC=CC=N1)(F)=O CN1CCCN2C1=NCCC2 c1ccccc1-c2ccc(CF)cc2 26
c1ccccc1-c2ccc(CO)cc2 O=S(C1=CC=CC=N1)(F)=O CC(C)(C)N=C(N(C)C)N(C)C c1ccccc1-c2ccc(CF)cc2 57
c1ccccc1-c2ccc(CO)cc2 O=S(C1=CC=CC=N1)(F)=O CC(C)(C)N=P(N1CCCC1)(N2CCCC2)N3CCCC3 c1ccccc1-c2ccc(CF)cc2 77
c1ccccc1-c2ccc(CO)cc2 O=S(C1=CC=C(C(F)(F)F)C=C1)(F)=O N\2=C1\N(CCCCC1)CCC/2 c1ccccc1-c2ccc(CF)cc2 17
c1ccccc1-c2ccc(CO)cc2 O=S(C1=CC=C(C(F)(F)F)C=C1)(F)=O CN1CCCN2C1=NCCC2 c1ccccc1-c2ccc(CF)cc2 36
c1ccccc1-c2ccc(CO)cc2 O=S(C1=CC=C(C(F)(F)F)C=C1)(F)=O CC(C)(C)N=C(N(C)C)N(C)C c1ccccc1-c2ccc(CF)cc2 83
c1ccccc1-c2ccc(CO)cc2 O=S(C1=CC=C(C(F)(F)F)C=C1)(F)=O CC(C)(C)N=P(N1CCCC1)(N2CCCC2)N3CCCC3 c1ccccc1-c2ccc(CF)cc2 99
c1ccccc1-c2ccc(CO)cc2 O=S(C1=CC=C([N+]([O-])=O)C=C1)(F)=O N\2=C1\N(CCCCC1)CCC/2 c1ccccc1-c2ccc(CF)cc2 21
c1ccccc1-c2ccc(CO)cc2 O=S(C1=CC=C([N+]([O-])=O)C=C1)(F)=O CN1CCCN2C1=NCCC2 c1ccccc1-c2ccc(CF)cc2 41
c1ccccc1-c2ccc(CO)cc2 O=S(C1=CC=C([N+]([O-])=O)C=C1)(F)=O CC(C)(C)N=C(N(C)C)N(C)C c1ccccc1-c2ccc(CF)cc2 83
c1ccccc1-c2ccc(CO)cc2 O=S(C1=CC=C([N+]([O-])=O)C=C1)(F)=O CC(C)(C)N=P(N1CCCC1)(N2CCCC2)N3CCCC3 c1ccccc1-c2ccc(CF)cc2 91
c1ccccc1-c2ccc(CO)cc2 C(C(C(F)(F)S(=O)(=O)F)(F)F)(C(F)(F)F)(F)F N\2=C1\N(CCCCC1)CCC/2 c1ccccc1-c2ccc(CF)cc2 23
c1ccccc1-c2ccc(CO)cc2 C(C(C(F)(F)S(=O)(=O)F)(F)F)(C(F)(F)F)(F)F CN1CCCN2C1=NCCC2 c1ccccc1-c2ccc(CF)cc2 37
c1ccccc1-c2ccc(CO)cc2 C(C(C(F)(F)S(=O)(=O)F)(F)F)(C(F)(F)F)(F)F CC(C)(C)N=C(N(C)C)N(C)C c1ccccc1-c2ccc(CF)cc2 48
c1ccccc1-c2ccc(CO)cc2 C(C(C(F)(F)S(=O)(=O)F)(F)F)(C(F)(F)F)(F)F CC(C)(C)N=P(N1CCCC1)(N2CCCC2)N3CCCC3 c1ccccc1-c2ccc(CF)cc2 68
O[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 Clc1ccc(S(=O)(=O)F)cc1 N\2=C1\N(CCCCC1)CCC/2 F[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 1
O[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 Clc1ccc(S(=O)(=O)F)cc1 CN1CCCN2C1=NCCC2 F[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 1
O[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 Clc1ccc(S(=O)(=O)F)cc1 CC(C)(C)N=C(N(C)C)N(C)C F[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 1
O[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 Clc1ccc(S(=O)(=O)F)cc1 CC(C)(C)N=P(N1CCCC1)(N2CCCC2)N3CCCC3 F[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 3
O[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 O=S(C1=CC=CC=N1)(F)=O N\2=C1\N(CCCCC1)CCC/2 F[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 1
O[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 O=S(C1=CC=CC=N1)(F)=O CN1CCCN2C1=NCCC2 F[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 2
O[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 O=S(C1=CC=CC=N1)(F)=O CC(C)(C)N=C(N(C)C)N(C)C F[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 1
O[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 O=S(C1=CC=CC=N1)(F)=O CC(C)(C)N=P(N1CCCC1)(N2CCCC2)N3CCCC3 F[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 1
O[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 O=S(C1=CC=C(C(F)(F)F)C=C1)(F)=O N\2=C1\N(CCCCC1)CCC/2 F[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 3
O[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 O=S(C1=CC=C(C(F)(F)F)C=C1)(F)=O CN1CCCN2C1=NCCC2 F[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 4
O[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 O=S(C1=CC=C(C(F)(F)F)C=C1)(F)=O CC(C)(C)N=C(N(C)C)N(C)C F[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 5
O[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 O=S(C1=CC=C(C(F)(F)F)C=C1)(F)=O CC(C)(C)N=P(N1CCCC1)(N2CCCC2)N3CCCC3 F[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 12
O[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 O=S(C1=CC=C([N+]([O-])=O)C=C1)(F)=O N\2=C1\N(CCCCC1)CCC/2 F[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 11
O[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 O=S(C1=CC=C([N+]([O-])=O)C=C1)(F)=O CN1CCCN2C1=NCCC2 F[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 12
O[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 O=S(C1=CC=C([N+]([O-])=O)C=C1)(F)=O CC(C)(C)N=C(N(C)C)N(C)C F[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 12
O[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 O=S(C1=CC=C([N+]([O-])=O)C=C1)(F)=O CC(C)(C)N=P(N1CCCC1)(N2CCCC2)N3CCCC3 F[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 22
O[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 C(C(C(F)(F)S(=O)(=O)F)(F)F)(C(F)(F)F)(F)F N\2=C1\N(CCCCC1)CCC/2 F[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 83
O[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 C(C(C(F)(F)S(=O)(=O)F)(F)F)(C(F)(F)F)(F)F CN1CCCN2C1=NCCC2 F[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 79
O[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 C(C(C(F)(F)S(=O)(=O)F)(F)F)(C(F)(F)F)(F)F CC(C)(C)N=C(N(C)C)N(C)C F[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 89
O[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 C(C(C(F)(F)S(=O)(=O)F)(F)F)(C(F)(F)F)(F)F CC(C)(C)N=P(N1CCCC1)(N2CCCC2)N3CCCC3 F[C@@H]1C[C@H](OCC2=CC=CC=C2)C1 82
O[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 Clc1ccc(S(=O)(=O)F)cc1 N\2=C1\N(CCCCC1)CCC/2 F[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 25
O[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 Clc1ccc(S(=O)(=O)F)cc1 CN1CCCN2C1=NCCC2 F[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 30
O[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 Clc1ccc(S(=O)(=O)F)cc1 CC(C)(C)N=C(N(C)C)N(C)C F[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 29
O[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 Clc1ccc(S(=O)(=O)F)cc1 CC(C)(C)N=P(N1CCCC1)(N2CCCC2)N3CCCC3 F[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 30
O[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 O=S(C1=CC=CC=N1)(F)=O N\2=C1\N(CCCCC1)CCC/2 F[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 45
O[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 O=S(C1=CC=CC=N1)(F)=O CN1CCCN2C1=NCCC2 F[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 40
O[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 O=S(C1=CC=CC=N1)(F)=O CC(C)(C)N=C(N(C)C)N(C)C F[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 39
O[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 O=S(C1=CC=CC=N1)(F)=O CC(C)(C)N=P(N1CCCC1)(N2CCCC2)N3CCCC3 F[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 33
O[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 O=S(C1=CC=C(C(F)(F)F)C=C1)(F)=O N\2=C1\N(CCCCC1)CCC/2 F[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 41
O[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 O=S(C1=CC=C(C(F)(F)F)C=C1)(F)=O CN1CCCN2C1=NCCC2 F[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 47
O[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 O=S(C1=CC=C(C(F)(F)F)C=C1)(F)=O CC(C)(C)N=C(N(C)C)N(C)C F[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 39
O[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 O=S(C1=CC=C(C(F)(F)F)C=C1)(F)=O CC(C)(C)N=P(N1CCCC1)(N2CCCC2)N3CCCC3 F[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 33
O[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 O=S(C1=CC=C([N+]([O-])=O)C=C1)(F)=O N\2=C1\N(CCCCC1)CCC/2 F[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 48
O[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 O=S(C1=CC=C([N+]([O-])=O)C=C1)(F)=O CN1CCCN2C1=NCCC2 F[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 48
O[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 O=S(C1=CC=C([N+]([O-])=O)C=C1)(F)=O CC(C)(C)N=C(N(C)C)N(C)C F[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 40
O[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 O=S(C1=CC=C([N+]([O-])=O)C=C1)(F)=O CC(C)(C)N=P(N1CCCC1)(N2CCCC2)N3CCCC3 F[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 32
O[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 C(C(C(F)(F)S(=O)(=O)F)(F)F)(C(F)(F)F)(F)F N\2=C1\N(CCCCC1)CCC/2 F[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 59
O[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 C(C(C(F)(F)S(=O)(=O)F)(F)F)(C(F)(F)F)(F)F CN1CCCN2C1=NCCC2 F[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 74
O[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 C(C(C(F)(F)S(=O)(=O)F)(F)F)(C(F)(F)F)(F)F CC(C)(C)N=C(N(C)C)N(C)C F[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 64
O[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 C(C(C(F)(F)S(=O)(=O)F)(F)F)(C(F)(F)F)(F)F CC(C)(C)N=P(N1CCCC1)(N2CCCC2)N3CCCC3 F[C@H]1C[C@@H](C(OC)=O)N(C(OC(C)(C)C)=O)C1 58
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