Desamino Chloro (S)-Fluoxetine

Base Information

• Chemical Name: Desamino Chloro (S)-Fluoxetine
• CAS No.: 114446-51-4
• Molecular Formula: C16H14ClF3O
• Molecular Weight: 314.7299696
• DSSTox Substance ID: DTXSID20446603
• Nikkaji Number: J1.365.963J
• Mol file: 114446-51-4.mol

Synonyms:Desamino Chloro (S)-Fluoxetine;114446-51-4;1-[(1S)-3-CHLORO-1-PHENYLPROPOXY]-4-(TRIFLUOROMETHYL)BENZENE;SCHEMBL2690834;DTXSID20446603;1-(Trifluoromethyl)-4-[(S)-1-phenyl-3-chloropropoxy]benzene

Chemical Property of Desamino Chloro (S)-Fluoxetine

Chemical Property:

• PSA: 9.23000
• LogP: 5.45440
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 314.0685272
• Heavy Atom Count: 21
• Complexity: 294

Purity/Quality:

98% ^*data from raw suppliers

DesaminoChloro(S)-Fluoxetine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(CCCl)OC2=CC=C(C=C2)C(F)(F)F
• Isomeric SMILES: C1=CC=C(C=C1)[C@H](CCCl)OC2=CC=C(C=C2)C(F)(F)F
• Uses: Fluoxetine (F597100) derivative.

Technology Process of Desamino Chloro (S)-Fluoxetine

There total 7 articles about Desamino Chloro (S)-Fluoxetine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 66.0%

4-hydroxybenzotrifluoride (402-45-9) + (1R)-3-chloro-1-phenylpropanol (100306-33-0,125712-82-5) → -(-)-1-chloro-3-phenyl-3-<4-(trifluoromethyl)phenoxy>propane (114446-51-4)

Guidance literature:

4-hydroxybenzotrifluoride; With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 4h; Inert atmosphere;

(1R)-3-chloro-1-phenylpropanol; In tetrahydrofuran; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.bmc.2008.10.065

Reference yield: 65.0%

(1R)-3-chloro-1-phenylpropanol (100306-33-0,125712-82-5) + α,α,α-trifluoro-p-cresol (402-45-9) → -(-)-1-chloro-3-phenyl-3-<4-(trifluoromethyl)phenoxy>propane (114446-51-4)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; Ambient temperature;

DOI:10.1021/jo00248a005

Reference yield: 54.0%

4-hydroxybenzotrifluoride (402-45-9) + 3-chloro-1-phenyl-propan-1-ol (18776-12-0,125712-82-5) → -(-)-1-chloro-3-phenyl-3-<4-(trifluoromethyl)phenoxy>propane (114446-51-4)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃;

DOI:10.1039/b000846j

upstream raw materials:

4-hydroxybenzotrifluoride

(1R)-3-chloro-1-phenylpropanol

α,α,α-trifluoro-p-cresol

3-chloro-1-phenyl-propan-1-ol

Downstream raw materials:

-(+)-fluoxetine hydrochloride

(S)-fluoxetine

(S)-1-phthalimido-3-(4-trifluormethyl-phenoxy)-3-phenyl-propane

N'-(S)-[1-(1-naphthyl)ethyl]-N-(S)-3-[4-(trifluoromethyl)phenoxy]-3-phenylpropylurea

Refernces

• 1、 Liu, Hui-Ling,Hoff, Bard Helge,Anthonsen, Thorleif. "Chemoenzymatic synthesis of the non-tricyclic antidepressants Fluoxetine, Tomoxetine and Nisoxetine". . p. 1767 - 1769. Retrieved 2007/10/03.
• 2、 -. "Novel process of producing phenyl or substituted phenylalkylamine pharmaceutical agents and novel chiral intermediates of high enantiomeric purity useful therein". . . Retrieved 2008/06/13.