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Top quality factory supply 100306-34-1 (S)-3-Chloro-1-phenyl-1-propanol at low price
- Molecular Formula:C9H11ClO
- Molecular Weight:170.639
- Appearance/Colour:white to light yellow crystal powder
- Vapor Pressure:0.000651mmHg at 25°C
- Melting Point:58-60 °C(lit.)
- Refractive Index:1.543
- Boiling Point:296.4 °C at 760 mmHg
- PKA:13.92±0.20(Predicted)
- Flash Point:132 °C
- PSA：20.23000
- Density:1.149 g/cm3
- LogP:2.34890
(S)-3-Chloro-1-phenyl-1-propanol(Cas 100306-34-1) Usage
|
General Description |
(S)-3-Chloro-1-phenyl-1-propanol ((S)-CPPO) is a valuable chiral intermediate used in the synthesis of antidepressant drugs, such as fluoxetine. It can be enantioselectively produced through microbial or enzymatic reduction of 3-chloro-1-phenyl-1-propanone (3-CPP), demonstrating its significance as a building block in pharmaceutical synthesis. The biocatalytic methods employed for its preparation, such as using recombinant Escherichia coli or yeast reductases, highlight its role in efficient and stereoselective synthetic routes. |
InChI:InChI=1/C9H11ClO/c10-7-6-9(11)8-4-2-1-3-5-8/h1-5,9,11H,6-7H2/t9-/m0/s1
100306-34-1 Relevant articles
Preparation of fluoxetine by multiple flow processing steps
Ahmed-Omer, Batoul,Sanderson, Adam J.
, p. 3854 - 3862 (2011)
Microflow technology is established as a...
Production of chiral compound using recombinant Escherichia coli cells co-expressing reductase and glucose dehydrogenase in an ionic liquid/water two phase system
Choi, Hye Jeong,Uhm, Ki-Nam,Kim, Hyung-Kwoun
, p. 114 - 118 (2011)
(S)-3-Chloro-1-phenyl-1-propanol ((S)-CP...
Asymmetric reduction of ketones by employing Rhodotorula sp. AS2.2241 and synthesis of the β-blocker (R)-nifenalol
Yang, Wei,Xu, Jian-He,Xie, Yan,Xu, Yi,Zhao, Gang,Lin, Guo-Qiang
, p. 1769 - 1774 (2006)
A broad range of prochiral ketones were ...
Total Synthesis of Meayamycin B
Basu, Upamanyu,Bressin, Robert K.,Koide, Kazunori,Osman, Sami,Pohorilets, Ivanna
supporting information, p. 4637 - 4647 (2020/05/01)
Meayamycin B is currently the most poten...
Efficient Synthesis of (R)-2-Chloro-1-(2,4-dichlorophenyl)ethanol with a Ketoreductase from Scheffersomyces stipitis CBS 6045
Shang, Yue-Peng,Chen, Qi,Kong, Xu-Dong,Zhang, Yu-Jun,Xu, Jian-He,Yu, Hui-Lei
supporting information, p. 426 - 431 (2017/02/10)
By enzyme screening, a ketoreductase clo...
A convenient enantioselective CBS-reduction of arylketones in flow-microreactor systems
De Angelis, Sonia,De Renzo, Maddalena,Carlucci, Claudia,Degennaro, Leonardo,Luisi, Renzo
supporting information, p. 4304 - 4311 (2016/05/24)
A convenient, versatile, and green CBS-a...
Chiral N-heterocyclic carbene iridium catalyst for the enantioselective hydrosilane reduction of ketones
Manabe, Yoshiki,Shinohara, Kanako,Nakamura, Hanako,Teramoto, Hiro,Sakaguchi, Satoshi
, p. 138 - 145 (2016/06/15)
Enantioselective reduction of ketones wi...
100306-34-1 Process route
-
-
936-59-4
3-chloropropiophenone
-
-
100306-34-1,125712-82-5
3-chloro-1-phenylpropanol
-
-
100306-33-0,125712-82-5
(1R)-3-chloro-1-phenylpropanol
| Conditions | Yield |
|---|---|
|
With
dimethylsulfide borane complex; C23H22BNO3;
In
tetrahydrofuran;
at 20 ℃;
for 2h;
Reagent/catalyst;
|
75% |
|
With
dimethylsulfide borane complex;
(+)-3-exo-amino-7,7-dimethoxynorbornan-2-exo-ol;
In
tetrahydrofuran;
at 25 ℃;
for 2h;
|
65% |
|
With
dimethylsulfide borane complex;
chiral diphenyloxazaborolidine;
In
tetrahydrofuran;
at 25 ℃;
Yield given. Yields of byproduct given. Title compound not separated from byproducts;
|
|
|
With
lithium borohydride; N,N′-dibenzoyl-L-cysteine; tert-butyl alcohol;
In
tetrahydrofuran;
at -78 - -30 ℃;
for 9h;
Yield given. Yields of byproduct given. Title compound not separated from byproducts;
|
|
|
With
9-borabicyclo[3.3.1]nonane dimer; borane-THF; (S)-diphenylprolinol;
In
tetrahydrofuran;
at 20 ℃;
for 1h;
Title compound not separated from byproducts;
|
|
|
With
borane; (2R,3S,4S,5R)-2,5-diamino-1,6-diphenyl-3,4-hexanediol;
In
tetrahydrofuran;
at 35 ℃;
for 5h;
Title compound not separated from byproducts;
|
|
|
chiral benzodioxole-based copper;
In
tetrahydrofuran; toluene; tert-butyl alcohol;
at -78 ℃;
for 8h;
Title compound not separated from byproducts;
|
|
|
With
dimethylsulfide borane complex;
In
tetrahydrofuran;
at 20 ℃;
Title compound not separated from byproducts.;
|
|
|
With
hydrogen;
Cp*Ir(OTf)[(S,S)-Msdpen];
In
methanol;
at 60 ℃;
for 24h;
under 7600.51 Torr;
Product distribution / selectivity;
|
77 % ee |
|
With
ketoreductase 108; NADPH;
at 30 ℃;
pH=6.0;
optical yield given as %ee;
aq. phosphate buffer;
Enzymatic reaction;
|
|
|
With
borane N,N-diethylaniline complex; (S)-Corey-Bakshi-Shibata oxazaborolidine;
In
1,2-dimethoxyethane; dichloromethane; water;
at 25 - 30 ℃;
for 12h;
optical yield given as %ee;
enantioselective reaction;
Inert atmosphere;
|
|
|
With
sodium t-butanolate; tert-butyl alcohol; (S)-2,2',6,6'-tetramethoxy-4,4'-bis(di(3,5-xylyl)phosphino)-3,3'-bipyridine;
In
toluene;
at 0 ℃;
for 14h;
Overall yield = 90 %;
|
88 % ee |
|
With
[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; (S,S,S,S)-N,N-bis(1,2-diphenylethylenediamino)-1,3-benzenedisulfonylamine; sodium formate;
In
water;
at 60 ℃;
for 11h;
enantioselective reaction;
Inert atmosphere;
|
85.2 % ee |
|
With
diborane; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole;
|
82 % ee |
|
With
dimethylsulfide borane complex; (1R,2S,3R,5R)-2-(1',3',2'-dioxaborolan-2'-yloxy)apopinan-3-amine;
In
tetrahydrofuran;
at 20 ℃;
for 1h;
Overall yield = 96 %; enantioselective reaction;
|
80 % ee |
|
With
diborane; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole;
In
tetrahydrofuran; 2-methyltetrahydrofuran;
at 0 ℃;
Solvent;
Temperature;
Overall yield = 94 %; Overall yield = 92 mg; enantioselective reaction;
Flow reactor;
Green chemistry;
|
80 % ee |
|
With
silver tetrafluoroborate; diethoxymethylane; C26H29N3O2*Cl(1-)*Ir(1+)*C8H12;
at 20 ℃;
for 20h;
Overall yield = 82 %; stereoselective reaction;
|
66 % ee |
|
With
D-glucose; dehydrogenase from Bacillus megaterium; ketoreductase cloned from Scheffersomyces stipitis CBS 6045; NADP;
In
aq. phosphate buffer; dimethyl sulfoxide;
at 30 ℃;
for 6h;
pH=6.5;
enantioselective reaction;
|
87.7 % ee |
|
With
sodium tetrahydroborate; borane-THF; (R)-1,1'-Bi-2-naphthol;
In
tetrahydrofuran;
at -78 - 24 ℃;
for 12h;
Overall yield = 49 percentSpectr.;
|
-
-
936-59-4
3-chloropropiophenone
-
-
100306-34-1,125712-82-5
3-chloro-1-phenylpropanol
| Conditions | Yield |
|---|---|
|
With
potassium formate;
Cp*IrCl[(S,S)-MsDPEN];
In
water; toluene;
at 50 ℃;
for 24h;
Product distribution / selectivity;
|
94% |
|
3-chloropropiophenone;
With
(S)-2,2',6,6'-tetramethoxy-4,4'-bis(diphenylphosphino)-3,3'-bipyridine; phenylsilane; copper(II) acetate monohydrate;
In
toluene;
at -20 ℃;
for 48h;
With
hydrogenchloride;
In
water; toluene;
Reagent/catalyst;
enantioselective reaction;
|
94% |
|
With
dimethylsulfide borane complex; (R)-2-[(1,3,2-dioxaborolan-2-yloxy)diphenylmethyl]pyrrolidine;
In
tetrahydrofuran;
at 20 ℃;
for 2h;
|
94% |
|
With
dimethylsulfide borane complex; (R)-2-[(1,3,2-dioxaborolan-2-yloxy)diphenylmethyl]pyrrolidine;
In
tetrahydrofuran;
at 20 ℃;
for 2.16667h;
|
94% |
|
With
borane N,N-diethylaniline complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole;
In
dichloromethane; toluene;
at -7 - 20 ℃;
for 0.166667h;
optical yield given as %ee;
enantioselective reaction;
|
88% |
|
With
potassium phosphate; Candida tenuis xylose reductase; NADH;
In
methanol;
for 24h;
|
80% |
|
3-chloropropiophenone;
With
borane N,N-diethylaniline complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole;
In
toluene;
at 20 ℃;
for 6h;
Inert atmosphere;
With
hydrogenchloride;
In
methanol; water; toluene;
for 0.166667h;
optical yield given as %ee;
enantioselective reaction;
Inert atmosphere;
|
79% |
|
With
borane; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole;
In
tetrahydrofuran;
optical yield given as %ee;
|
77% |
|
With
(S)-2,2',6,6'-tetramethoxy-4,4'-bis(diphenylphosphino)-3,3'-bipyridine; phenylsilane; copper(II) acetate monohydrate;
In
toluene;
at -20 ℃;
for 24h;
Inert atmosphere;
Schlenk technique;
|
73% |
|
With
potassium phosphate buffer; Rhodotorula sp. AS22241;
at 30 ℃;
for 20h;
pH=7.0;
|
50% |
|
With
dIpc2BCl;
In
tetrahydrofuran;
at -25 ℃;
Product distribution;
other ring and chain substituted haloaralkyl ketones;
|
|
|
Multi-step reaction with 3 steps
1: 88 percent / NaBH4 / ethanol / 2 h / 20 °C
2: 93 percent / pyridine; DMAP / CH2Cl2 / 0 - 20 °C
3: aq. phosphate buffer; Novozyme 435 / 288 h / 30 °C / pH 7
With
pyridine; dmap; sodium tetrahydroborate; phosphate buffer; novozyme 435;
In
ethanol; dichloromethane;
1: Reduction / 2: Esterification / 3: Hydrolysis;
|
|
|
Multi-step reaction with 2 steps
1: 88 percent / NaBH4 / ethanol / 2 h / 20 °C
2: 33 percent / Novozyme 435 / hexane / 192 h / 30 °C
With
sodium tetrahydroborate; novozyme 435;
In
ethanol; hexane;
1: Reduction / 2: Esterification;
|
|
|
Multi-step reaction with 4 steps
1: LiAlH4 / diethyl ether
2: pyridine / CH2Cl2
4: 100 percent / K2CO3, MeOH
With
pyridine; methanol; lithium aluminium tetrahydride; potassium carbonate;
In
diethyl ether; dichloromethane;
|
|
|
With
(S)-2,2',6,6'-tetramethoxy-4,4'-bis(diphenylphosphino)-3,3'-bipyridine; phenylsilane; copper diacetate;
In
toluene;
at -20 ℃;
for 36h;
stereoselective reaction;
|
|
|
With
NADPH; 1-butyl-3-methylimidazolium trifluoromethanesulfonimide;
In
Tween-40;
for 8h;
pH=7 - 7.5;
optical yield given as %ee;
enantioselective reaction;
Tris-HCl buffer;
Enzymatic reaction;
|
100 mmol |
|
With
yeast culture of Candida viswanathii KCh 120;
In
acetone;
at 25 ℃;
for 24h;
enantioselective reaction;
Microbiological reaction;
|
84 mg |
|
With
potassium phosphate; Candida tenuis xylose reductase; NADH;
In
methanol;
for 24h;
|
100306-34-1 Upstream products
-
936-59-4
3-chloropropiophenone
-
142037-19-2
Chloro-acetic acid (S)-3-chloro-1-phenyl-propyl ester
-
108-22-5
Isopropenyl acetate
-
18776-12-0
3-chloro-1-phenyl-propan-1-ol
100306-34-1 Downstream products
-
145294-62-8
(R)-(+)-1-chloro-3-(4-iodo-2-methylphenoxy)-3-phenylpropane
-
114133-36-7
(S)-(-)-3-iodo-1-phenyl-1-propanol
-
114446-47-8
-(-)-1-chloro-3-phenyl-3-(2-methylphenoxy)propane -
114446-48-9
-(+)-1-chloro-3-phenyl-3-<4-(trifluoromethyl)phenoxy>propane
Relative Products
- Acid Yellow 114
- Lodoxamidetromethamine
- 5-Bromoindole
- Tetraheptylammonium bromide
- THIODIGLYCOLIC ACID
- TERPIN MONOHYDRATE
- Dichloro(p-cymene)ruthenium(II) dimer
- N-Benzoyl-5'-O-(4,4-Dimethoxytrityl)-2'-O-[(tert-butyl)dimethylsilyl]adenosine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite
- 2,5-Dibromopyridine
- 5-Amino-2,4,6-triiodoisophthalic acid
- Solvent Blue 36
- 4(3H)-Quinazolinone, 3-(2-bromophenyl)-2-methyl-
- D-Tetrandrine
- Dysprosium163
- 3,4-dihydroxystyrene
- Pyrrolo[3,4-c]pyrrole-1,4-dione, 3,6-bis(4-bromophenyl)-2,5-dihydro-
- PARTIALLY HYDROGENATED ROSIN
- N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid disodium salt
- Imperatorin
- Anethole