Alternatived Products of [ 95484-17-6 ]
Product Details of [ 95484-17-6 ]
CAS No. : 95484-17-6
MDL No. : MFCD26516661
Formula :
C12 H15 NO3
Boiling Point :
-
Linear Structure Formula : -
InChI Key : QVWVVHRNMKYYBJ-UHFFFAOYSA-N
M.W : 221.25
Pubchem ID : 11368024
Synonyms :
Calculated chemistry of [ 95484-17-6 ]
Physicochemical Properties
Num. heavy atoms :
16
Num. arom. heavy atoms :
6
Fraction Csp3 :
0.33
Num. rotatable bonds :
7
Num. H-bond acceptors :
3.0
Num. H-bond donors :
1.0
Molar Refractivity :
60.12
TPSA :
55.4 Ų
Pharmacokinetics
GI absorption :
High
BBB permeant :
Yes
P-gp substrate :
No
CYP1A2 inhibitor :
Yes
CYP2C19 inhibitor :
No
CYP2C9 inhibitor :
No
CYP2D6 inhibitor :
No
CYP3A4 inhibitor :
No
Log Kp (skin permeation) :
-6.88 cm/s
Lipophilicity
Log Po/w (iLOGP) :
2.41
Log Po/w (XLOGP3) :
1.09
Log Po/w (WLOGP) :
1.74
Log Po/w (MLOGP) :
1.45
Log Po/w (SILICOS-IT) :
1.92
Consensus Log Po/w :
1.72
Druglikeness
Lipinski :
0.0
Ghose :
None
Veber :
0.0
Egan :
0.0
Muegge :
0.0
Bioavailability Score :
0.55
Water Solubility
Log S (ESOL) :
-1.71
Solubility :
4.27 mg/ml ; 0.0193 mol/l
Class :
Very soluble
Log S (Ali) :
-1.85
Solubility :
3.16 mg/ml ; 0.0143 mol/l
Class :
Very soluble
Log S (SILICOS-IT) :
-3.7
Solubility :
0.0446 mg/ml ; 0.000201 mol/l
Class :
Soluble
Medicinal Chemistry
PAINS :
0.0 alert
Brenk :
0.0 alert
Leadlikeness :
1.0
Synthetic accessibility :
2.04
Application In Synthesis of [ 95484-17-6 ]
* 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 [ 95484-17-6 ]
1
[ 55-27-6 ]
[ 95484-17-6 ]
{3-[2-(3,4-Dihydroxy-phenyl)-2-hydroxy-ethylamino]-butyl}-carbamic acid benzyl ester; hydrochloride
[ No CAS ]
Yield Reaction Conditions Operation in experiment
47%
With sodium cyanoborohydride In methanol at 50℃;
2
[ 76197-40-5 ]
[ 100-51-6 ]
[ 95484-17-6 ]
Yield Reaction Conditions Operation in experiment
In benzene for 17h; Heating; Yield given;
3
[ 621-84-1 ]
[ 78-94-4 ]
[ 95484-17-6 ]
Yield Reaction Conditions Operation in experiment
88%
In dichloromethane at 20℃; for 14h;
83%
With Nafion(R) SAC-13 In acetonitrile at 20℃; for 12h;
76%
at 20℃;
60%
With dichloro bis(acetonitrile) palladium(II) In dichloromethane at 20℃; for 24h; Inert atmosphere;
Reference:
[1]Gaunt, Matthew J.; Spencer, Jonathan B.
[Organic Letters, 2001, vol. 3, # 1, p. 25 - 28]
[2]Wabnitz, Tobias C.; Yu, Jin-Quan; Spencer, Jonathan B.
[Synlett, 2003, # 7, p. 1070 - 1072]
[3]Srivastava, Neeta; Banik, Bimal K.
[Journal of Organic Chemistry, 2003, vol. 68, # 6, p. 2109 - 2114]
[4]Nonaka, Shiori; Sugimoto, Kenji; Ueda, Hirofumi; Tokuyama, Hidetoshi
[Advanced Synthesis and Catalysis, 2016, vol. 358, # 3, p. 380 - 385]
4
[ 621-84-1 ]
[ 78-94-4 ]
[ 95484-17-6 ]
bis-(3-oxo-butyl)-carbamic acid benzyl ester
[ No CAS ]
Yield Reaction Conditions Operation in experiment
1: 81%
2: 18%
In acetonitrile at 20℃; for 4h;
5
[ 867-13-0 ]
[ 95484-17-6 ]
[ 612065-56-2 ]
Yield Reaction Conditions Operation in experiment
78%
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: 4-N-(benzyloxycarbonyl)-butan-2-one In tetrahydrofuran at 20℃;
6
[ 7396-44-3 ]
[ 95484-17-6 ]
[ 612065-80-2 ]
7
[ 612065-83-5 ]
[ 95484-17-6 ]
Yield Reaction Conditions Operation in experiment
85%
With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -60℃;
8
[ 65564-05-8 ]
[ 95484-17-6 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 77 percent / tetrahydrofuran / -78 °C
2: 85 percent / (COCl)2; DMSO / CH2 Cl2 / -60 °C
9
[ 34637-22-4 ]
[ 95484-17-6 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: 83 percent / (COCl)2; DMSO / CH2 Cl2 / -60 °C
2: 77 percent / tetrahydrofuran / -78 °C
3: 85 percent / (COCl)2; DMSO / CH2 Cl2 / -60 °C
10
[ 501-53-1 ]
[ 95484-17-6 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: 92 percent / Na2 CO3 / H2 O
2: 83 percent / (COCl)2; DMSO / CH2 Cl2 / -60 °C
3: 77 percent / tetrahydrofuran / -78 °C
4: 85 percent / (COCl)2; DMSO / CH2 Cl2 / -60 °C
11
[ 95484-17-6 ]
2-hydroxy-(6-methyl-2-oxo-[1,3]oxazinan-6-yl)acetic acid ethyl ester
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C
1.2: 78 percent / tetrahydrofuran / 20 °C
2.1: 71 percent / m-CPBA / CH2 Cl2 / 24 h / Heating
3.1: 80 percent / BF3 *Et2 O / CH2 Cl2 / 2 h / -78 °C
4.1: 100 percent / hydrogen / Pd-C / ethanol / 12 h / 760 Torr
12
[ 95484-17-6 ]
(1R,6R)-6-Methyl-2-oxo-7-oxa-3-aza-bicyclo[4.1.0]heptane-3-carboxylic acid benzyl ester
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C
1.2: 78 percent / tetrahydrofuran / 20 °C
2.1: 94 percent / AD-mix-β; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 0 °C
3.1: 83 percent / Et3 N / CH2 Cl2
4.1: 90 percent / K2 CO3 / ethanol
5.1: NaH / dimethylformamide
13
[ 95484-17-6 ]
(2R,3R)-3-(2-Benzyloxycarbonylamino-ethyl)-3-methyl-oxirane-2-carboxylic acid ethyl ester
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C
1.2: 78 percent / tetrahydrofuran / 20 °C
2.1: 94 percent / AD-mix-β; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 0 °C
3.1: 83 percent / Et3 N / CH2 Cl2
4.1: 90 percent / K2 CO3 / ethanol
14
[ 95484-17-6 ]
3-(2-benzyloxycarbonylaminoethyl)-3-methyloxirane-2-carboxylic acid ethyl ester
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C
1.2: 78 percent / tetrahydrofuran / 20 °C
2.1: 71 percent / m-CPBA / CH2 Cl2 / 24 h / Heating
15
[ 95484-17-6 ]
(S)-Benzyloxy-((S)-6-methyl-2-oxo-[1,3]oxazinan-6-yl)-acetic acid ethyl ester
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C
1.2: 78 percent / tetrahydrofuran / 20 °C
2.1: 71 percent / m-CPBA / CH2 Cl2 / 24 h / Heating
3.1: 80 percent / BF3 *Et2 O / CH2 Cl2 / 2 h / -78 °C
16
[ 95484-17-6 ]
[ 612065-57-3 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C
1.2: 78 percent / tetrahydrofuran / 20 °C
2.1: 94 percent / AD-mix-β; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 0 °C
17
[ 95484-17-6 ]
(6-methyl-2-oxo-[1,3]oxazinan-6-yl)(toluene-4-sulfonyloxy)acetic acid ethyl ester
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C
1.2: 78 percent / tetrahydrofuran / 20 °C
2.1: 71 percent / m-CPBA / CH2 Cl2 / 24 h / Heating
3.1: 80 percent / BF3 *Et2 O / CH2 Cl2 / 2 h / -78 °C
4.1: 100 percent / hydrogen / Pd-C / ethanol / 12 h / 760 Torr
5.1: 92 percent / pyridine / 20 °C
18
[ 95484-17-6 ]
(2R,3R)-3-(2-Benzyloxycarbonylamino-ethyl)-3-methyl-oxirane-2-carboxylic acid benzyl ester
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1.1: NaH / dimethylformamide / 0 °C
1.2: 80 percent / dimethylformamide / 20 °C
2.1: AD-mix-β; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 0 °C
3.1: Et3 N / CH2 Cl2
4.1: DBU
19
[ 95484-17-6 ]
[ 612065-81-3 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1.1: NaH / dimethylformamide / 0 °C
1.2: 80 percent / dimethylformamide / 20 °C
2.1: AD-mix-β; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 0 °C
20
[ 95484-17-6 ]
(2R,3S)-5-Benzyloxycarbonylamino-2,3-dihydroxy-3-methyl-pentanoic acid benzyl ester
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1.1: NaH / dimethylformamide / 0 °C
1.2: 80 percent / dimethylformamide / 20 °C
2.1: AD-mix-β; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 0 °C
21
[ 95484-17-6 ]
[ 612065-82-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C
1.2: 78 percent / tetrahydrofuran / 20 °C
2.1: 94 percent / AD-mix-β; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 0 °C
3.1: 83 percent / Et3 N / CH2 Cl2
22
[ 95484-17-6 ]
(2S,3R)-5-Benzyloxycarbonylamino-3-hydroxy-3-methyl-2-(toluene-4-sulfonyloxy)-pentanoic acid benzyl ester
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1.1: NaH / dimethylformamide / 0 °C
1.2: 80 percent / dimethylformamide / 20 °C
2.1: AD-mix-β; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 0 °C
3.1: Et3 N / CH2 Cl2
23
benzyl (3-(methoxy(methyl)amino)-3-oxopropyl)carbamate
[ No CAS ]
[ 75-16-1 ]
[ 95484-17-6 ]
Yield Reaction Conditions Operation in experiment
In tetrahydrofuran; diethyl ether at 0℃;
24
[ 14150-94-8 ]
[ 95484-17-6 ]
[ 1119103-51-3 ]
[ 1119103-57-9 ]
25
[ 95484-17-6 ]
[ 149-73-5 ]
benzyl 3,3-dimethoxybutylcarbamate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
69%
With toluene-4-sulfonic acid In methanol at 45℃; for 3.5h; Inert atmosphere;
26
[ 22065-57-2 ]
[ 95484-17-6 ]
1-benzyl 2-ethyl cis-3-hydroxy-3-methyl-2-phenylpyrrolidine-1,2-dicarboxylate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
96%
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)] In dichloromethane for 1.5h; Reflux; Inert atmosphere; diastereoselective reaction;
Reference:
[1]Nicolle, Simon M.; Lewis, William; Hayes, Christopher J.; Moody, Christopher J.
[Angewandte Chemie - International Edition, 2016, vol. 55, # 11, p. 3749 - 3753][Angew. Chem., 2016, vol. 128, # 11, p. 3813 - 3817,5]