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[ CAS No. 1025434-04-1 ] {[proInfo.proName]}

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Chemical Structure| 1025434-04-1
Chemical Structure| 1025434-04-1
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Product Details of [ 1025434-04-1 ]

CAS No. :1025434-04-1 MDL No. :MFCD02682488
Formula : C19H17NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :WKYFUFWCJIKRCS-KRWDZBQOSA-N
M.W : 323.34 Pubchem ID :66601066
Synonyms :
Chemical Name :(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)but-3-enoic acid

Calculated chemistry of [ 1025434-04-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 24
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.16
Num. rotatable bonds : 7
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 89.5
TPSA : 75.63 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.79 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.73
Log Po/w (XLOGP3) : 3.5
Log Po/w (WLOGP) : 3.16
Log Po/w (MLOGP) : 2.48
Log Po/w (SILICOS-IT) : 2.91
Consensus Log Po/w : 2.96

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -3.96
Solubility : 0.0356 mg/ml ; 0.00011 mol/l
Class : Soluble
Log S (Ali) : -4.77
Solubility : 0.00547 mg/ml ; 0.0000169 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.95
Solubility : 0.00365 mg/ml ; 0.0000113 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.57

Safety of [ 1025434-04-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501 UN#:N/A
Hazard Statements:H302-H312-H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1025434-04-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1025434-04-1 ]

[ 1025434-04-1 ] Synthesis Path-Downstream   1~27

  • 1
  • [ 1025434-04-1 ]
  • [ 500872-36-6 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride In dichloromethane at 20 - 40℃; for 2h;
With thionyl chloride In dichloromethane at 0℃; for 3h; Reflux; Inert atmosphere;
With thionyl chloride In dichloromethane at 0℃; for 3h; Reflux;
  • 2
  • [ 500872-35-5 ]
  • [ 1025434-04-1 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride In 1,4-dioxane at 80℃; for 48h;
  • 3
  • [ 1025434-04-1 ]
  • [3-(9<i>H</i>-fluoren-9-ylmethoxycarbonylamino)-2-oxo-3,6-dihydro-2<i>H</i>-benzo[<i>b</i>]azocin-1-yl]-acetic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: SOCl2 / CH2Cl2 / 2 h / 20 - 40 °C 2: 78 percent / CH2Cl2 / 16 h / 20 °C 3: 99 percent / Ru-containing catalyst / CH2Cl2 / 16 h / Heating
  • 4
  • [ 1025434-04-1 ]
  • [ 500872-38-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: SOCl2 / CH2Cl2 / 2 h / 20 - 40 °C 2: 78 percent / CH2Cl2 / 16 h / 20 °C
  • 5
  • [ 1025434-04-1 ]
  • [8-bromo-3-(9<i>H</i>-fluoren-9-ylmethoxycarbonylamino)-2-oxo-3,6-dihydro-2<i>H</i>-benzo[<i>b</i>]azocin-1-yl]-acetic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: SOCl2 / CH2Cl2 / 2 h / 20 - 40 °C 2: 65 percent / CH2Cl2 / 16 h / 20 °C 3: 94 percent / Ru-containing catalyst / CH2Cl2 / 16 h / Heating
  • 6
  • [ 1025434-04-1 ]
  • [3-(9<i>H</i>-fluoren-9-ylmethoxycarbonylamino)-8-methoxy-2-oxo-3,6-dihydro-2<i>H</i>-benzo[<i>b</i>]azocin-1-yl]-acetic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: SOCl2 / CH2Cl2 / 2 h / 20 - 40 °C 2: 77 percent / CH2Cl2 / 16 h / 20 °C 3: 99 percent / Ru-containing catalyst / CH2Cl2 / 16 h / Heating
  • 7
  • [ 1025434-04-1 ]
  • [ 500872-47-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: SOCl2 / CH2Cl2 / 2 h / 20 - 40 °C 2: 65 percent / CH2Cl2 / 16 h / 20 °C
  • 8
  • [ 1025434-04-1 ]
  • [ 500872-48-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: SOCl2 / CH2Cl2 / 2 h / 20 - 40 °C 2: 77 percent / CH2Cl2 / 16 h / 20 °C
  • 9
  • [ 500872-34-4 ]
  • [ 1025434-04-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: NaIO4 / methanol; H2O / 20 h / 0 - 20 °C 2: xylene / 72 h / 150 °C 3: aq. HCl / dioxane / 48 h / 80 °C
  • 10
  • methyl (2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-(methylsulfonyl)butanoate [ No CAS ]
  • [ 1025434-04-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: xylene / 72 h / 150 °C 2: aq. HCl / dioxane / 48 h / 80 °C
  • 11
  • [ 35661-60-0 ]
  • [ 35661-39-3 ]
  • [ 71989-23-6 ]
  • [ 71989-26-9 ]
  • [ 71989-35-0 ]
  • [ 71989-28-1 ]
  • [ 132388-59-1 ]
  • [ 132327-80-1 ]
  • [ 143824-78-6 ]
  • Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
  • [ 1025434-04-1 ]
  • H-(vinylglycyl)-QGTFTSDYSKYLDSRRAQDFVQWLMNTKRNRNNIA-NH2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide Automated synthesizer; solid phase reaction; Stage #2: solid phase reaction; Stage #3: Fmoc-Leu-OH; Fmoc-Ile-OH; Fmoc-Lys(tert-butoxycarbonyl); Fmoc-Thr(tBu)-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine; L-Asn(Trt); Fmoc-L-Gln(Trt)-OH; 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine; (S)-N-(Fmoc)vinylglycine Further stages;
  • 12
  • [ 1025434-04-1 ]
  • di-(tert-butyl) (2S,3E,6R)-6-[(tert-butoxycarbonyl)amino]-2-[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-heptenedioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: boron trifluoride diethyl etherate / dichloromethane; cyclohexane / Inert atmosphere 2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / Inert atmosphere; Reflux
  • 13
  • [ 98946-18-0 ]
  • [ 1025434-04-1 ]
  • tert-butyl (2S)-2-[(9H-(fluoren-9-ylmethoxy)carbonyl)]amino}-3-butenoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
933 mg With boron trifluoride diethyl etherate In dichloromethane; cyclohexane Inert atmosphere; 4.2.1 Cross-metathesis between allylglycine and vinylglycine derivatives General procedure: A solution of allylglycine derivative (0.50mmol) and vinylglycine derivative (0.90mmol) in dichloromethane (6mL) wasbubbled with Ar for 5min, and then cannulated into a flask containing the Grubbs' second generation catalyst (10mol%). Thereaction mixture was refluxed overnight. The mixture was concentrated in vacuo and the residue was purified by flash silica gel column chromatography (eluent: hexane/ethyl acetate 8:1 v/v) to afford the cross-coupled products 9 or 10, respectively.
  • 14
  • [ 24424-99-5 ]
  • [ 75266-38-5 ]
  • [ 1025434-04-1 ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate; In 1,4-dioxane; water;Inert atmosphere; Reflux; General procedure: A solution of allylglycine derivative (0.50mmol) and vinylglycine derivative (0.90mmol) in dichloromethane (6mL) wasbubbled with Ar for 5min, and then cannulated into a flask containing the Grubbs' second generation catalyst (10molpercent). Thereaction mixture was refluxed overnight. The mixture was concentrated in vacuo and the residue was purified by flash silica gel column chromatography (eluent: hexane/ethyl acetate 8:1 v/v) to afford the cross-coupled products 9 or 10, respectively.
  • 15
  • [ 1025434-04-1 ]
  • (S,S)-methyl 2-[N-[2-(N-Fmoc-amino)but-3-enoyl]-N-(2,4-dimethoxybenzyl)amino]hex-5-enoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride / dichloromethane / 3 h / 0 °C / Reflux; Inert atmosphere 2: dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere
  • 16
  • [ 1025434-04-1 ]
  • (S,S)-methyl 2-[N-[2-(N-Fmoc-amino)but-3-enoyl]-N-(2,4-dimethoxybenzyl)amino]hept-6-enoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride / dichloromethane / 3 h / 0 °C / Reflux; Inert atmosphere 2: dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere
  • 17
  • [ 1025434-04-1 ]
  • (3S,10S,Z) methyl 3-(N-Fmoc-amino)-1-(2,4-dimethoxybenzyl)-2-oxo-1,2,3,6,7,8-hexahydroazocine-8-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: thionyl chloride / dichloromethane / 3 h / 0 °C / Reflux; Inert atmosphere 2: dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 3: Grubbs catalyst first generation / dichloromethane / 72 h / Inert atmosphere; Reflux
  • 18
  • [ 1025434-04-1 ]
  • (3S,9S,Z)-methyl 3-(N-Fmoc-amino)-1-(2,4-dimethoxybenzyl)-2-oxo-1,2,3,6,7,8,9-heptahydro-1H-azonine-9-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: thionyl chloride / dichloromethane / 3 h / 0 °C / Reflux; Inert atmosphere 2: dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 3: Grubbs catalyst first generation / dichloromethane / 48 h / Inert atmosphere; Reflux
  • 19
  • [ 1025434-04-1 ]
  • (3S,8S,Z)-methyl 3-(N-Fmoc-amino)-2-oxo-1,2,3,6,7,8-hexahydroazocine-8-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: thionyl chloride / dichloromethane / 3 h / 0 °C / Reflux; Inert atmosphere 2: dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 3: Grubbs catalyst first generation / dichloromethane / 72 h / Inert atmosphere; Reflux 4: trifluoroacetic acid / dichloromethane / Inert atmosphere
  • 20
  • [ 1025434-04-1 ]
  • (3S,9S,Z)-methyl 3-(N-Fmoc-amino)-2-oxo-1,2,3,6,7,8,9-heptahydro-1H-azonine-9-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: thionyl chloride / dichloromethane / 3 h / 0 °C / Reflux; Inert atmosphere 2: dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 3: Grubbs catalyst first generation / dichloromethane / 48 h / Inert atmosphere; Reflux 4: trifluoroacetic acid / dichloromethane / Inert atmosphere
  • 21
  • [ 1025434-04-1 ]
  • (3R,4S,5S,8S)-methyl 3-(N-Fmoc-amino)-4-iodo-2-oxohexahydro-5H-pyrrolizine-8-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: thionyl chloride / dichloromethane / 3 h / 0 °C / Reflux; Inert atmosphere 2: dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 3: Grubbs catalyst first generation / dichloromethane / 72 h / Inert atmosphere; Reflux 4: trifluoroacetic acid / dichloromethane / Inert atmosphere 5: iodine; [bis(acetoxy)iodo]benzene / acetonitrile / 0.5 h / 80 °C / Inert atmosphere; Darkness
  • 22
  • [ 851909-11-0 ]
  • [ 1025434-04-1 ]
  • (Z,S)-methyl 2-[N-[2-(N-Fmoc-amino)but-3-enoyl]-N-(2,4-dimethoxybenzyl)amino]hex-5-enoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 24h; Inert atmosphere;
  • 23
  • [ 1025434-04-1 ]
  • (S,S)-methyl 2-[N-[2-(N-Fmoc-amino)but-3-enoyl]-N-(2,4-dimethoxybenzyl)amino]pent-4-enoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride / dichloromethane / 3 h / 0 °C / Reflux 2: dichloromethane / 3 h / 0 - 20 °C
  • 24
  • [ 1025434-04-1 ]
  • (3S,4R,5R,7S)-methyl 3-(N-Fmoc-amino)-5-iodo-6-acetoxy-2-oxoazocane-7-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: thionyl chloride / dichloromethane / 3 h / 0 °C / Reflux 2: dichloromethane / 3 h / 0 - 20 °C 3: Grubbs catalyst first generation / dichloromethane / 48 h / Reflux 4: trifluoroacetic acid / dichloromethane 5: iodine / toluene / 0.5 h / 80 °C
  • 25
  • [ 1025434-04-1 ]
  • (3S)-methyl 3-(N-Fmoc-amino)-2-oxo-2,3-dihydro-1H-azepine-7-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: thionyl chloride / dichloromethane / 3 h / 0 °C / Reflux 2: dichloromethane / 3 h / 0 - 20 °C 3: Grubbs catalyst first generation / dichloromethane / 48 h / Reflux 4: trifluoroacetic acid / dichloromethane 5: 1-<bis(adamantylcarbonyloxy)iodo>-4-methoxybenzene; iodine / toluene / 0.5 h / 80 °C / Darkness
  • 26
  • [ 1025434-04-1 ]
  • (3S,7S)-methyl 3-(N-Fmoc-amino)-1-(2,4-dimethoxybenzyl)-2-oxo-2,3,6,7-tetrahydro-1Hazepine-7-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: thionyl chloride / dichloromethane / 3 h / 0 °C / Reflux 2: dichloromethane / 3 h / 0 - 20 °C 3: Grubbs catalyst first generation / dichloromethane / 48 h / Reflux
  • 27
  • [ 1025434-04-1 ]
  • (3S,7S)-methyl 3-(N-Fmoc-amino)-2-oxo-2,3,6,7-tetrahydro-1H-azepine-7-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: thionyl chloride / dichloromethane / 3 h / 0 °C / Reflux 2: dichloromethane / 3 h / 0 - 20 °C 3: Grubbs catalyst first generation / dichloromethane / 48 h / Reflux 4: trifluoroacetic acid / dichloromethane
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