Alternatived Products of [ 1025434-04-1 ]
Product Details of [ 1025434-04-1 ]
CAS No. : 1025434-04-1
MDL No. : MFCD02682488
Formula :
C19 H17 NO4
Boiling Point : -
Linear Structure Formula : -
InChI Key : WKYFUFWCJIKRCS-KRWDZBQOSA-N
M.W : 323.34 Pubchem ID : 66601066
Synonyms :
Calculated chemistry of [ 1025434-04-1 ]
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 ]
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 ]
1
[ 1025434-04-1 ]
[ 500872-36-6 ]
Yield Reaction Conditions Operation 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;
Reference：
[1]Organ, Michael G; Xu, Juan; N'Zemba, Blaise
[Tetrahedron Letters, 2002, vol. 43, # 45, p. 8177 - 8180]
[2]Atmuri, N. D. Prasad; Lubell, William D.
[Journal of Organic Chemistry, 2015, vol. 80, # 10, p. 4904 - 4918]
[3]Atmuri, N.D. Prasad; Reilley, David J.; Lubell, William D.
[Organic Letters, 2017, vol. 19, # 19, p. 5066 - 5069]
2
[ 500872-35-5 ]
[ 1025434-04-1 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: SOCl2 / CH2 Cl2 / 2 h / 20 - 40 °C
2: 78 percent / CH2 Cl2 / 16 h / 20 °C
3: 99 percent / Ru-containing catalyst / CH2 Cl2 / 16 h / Heating
4
[ 1025434-04-1 ]
[ 500872-38-8 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: SOCl2 / CH2 Cl2 / 2 h / 20 - 40 °C
2: 78 percent / CH2 Cl2 / 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 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: SOCl2 / CH2 Cl2 / 2 h / 20 - 40 °C
2: 65 percent / CH2 Cl2 / 16 h / 20 °C
3: 94 percent / Ru-containing catalyst / CH2 Cl2 / 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 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: SOCl2 / CH2 Cl2 / 2 h / 20 - 40 °C
2: 77 percent / CH2 Cl2 / 16 h / 20 °C
3: 99 percent / Ru-containing catalyst / CH2 Cl2 / 16 h / Heating
7
[ 1025434-04-1 ]
[ 500872-47-9 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: SOCl2 / CH2 Cl2 / 2 h / 20 - 40 °C
2: 65 percent / CH2 Cl2 / 16 h / 20 °C
8
[ 1025434-04-1 ]
[ 500872-48-0 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: SOCl2 / CH2 Cl2 / 2 h / 20 - 40 °C
2: 77 percent / CH2 Cl2 / 16 h / 20 °C
9
[ 500872-34-4 ]
[ 1025434-04-1 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: NaIO4 / methanol; H2 O / 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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;
Reference：
[1]Location in patent: experimental part
Santoprete, Alessia; Capito, Elena; Carrington, Paul E.; Pocai, Alessandro; Finotto, Marco; Langella, Annunziata; Ingallinella, Paolo; Zytko, Karolina; Bufali, Simone; Cianetti, Simona; Veneziano, Maria; Bonelli, Fabio; Zhu, Lan; Monteagudo, Edith; Marsh, Donald J.; Sinharoy, Ranabir; Bianchi, Elisabetta; Pessi, Antonello
[Journal of Peptide Science, 2011, vol. 17, # 4, p. 270 - 280]
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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
Life Science
For Research Only
100K+ Compounds
Competitive Price
1-2 Day Shipping
