Cyclohexanone, 2-amino-2-(2-chlorophenyl)-6-hydroxy-

Base Information

• Chemical Name: Cyclohexanone, 2-amino-2-(2-chlorophenyl)-6-hydroxy-
• CAS No.: 81395-70-2
• Molecular Formula: C₁₂H₁₄ClNO₂
• Molecular Weight: 239.702
• UNII: 6VAD9SC8NW
• DSSTox Substance ID: DTXSID701001963
• Nikkaji Number: J3.637.847F
• Wikipedia: Hydroxynorketamine
• Wikidata: Q20164362
• ChEMBL ID: CHEMBL3544557
• Mol file: 81395-70-2.mol

Synonyms:(2R,6R)-HNK;(2R,6R)-hydroxynorketamine;6-hydroxynorketamine;6-hydroxynorketamine, (+-)-isomer;6-hydroxynorketamine, (2S-cis)-isomer

Chemical Property of Cyclohexanone, 2-amino-2-(2-chlorophenyl)-6-hydroxy-

Chemical Property:

• Vapor Pressure: 6.33E-08mmHg at 25°C
• Boiling Point: 423.4°C at 760 mmHg
• Flash Point: 209.9°C
• PSA: 63.32000
• Density: 1.316g/cm³
• LogP: 2.30820
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 239.0713064
• Heavy Atom Count: 16
• Complexity: 284

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CC(C(=O)C(C1)(C2=CC=CC=C2Cl)N)O

Technology Process of Cyclohexanone, 2-amino-2-(2-chlorophenyl)-6-hydroxy-

There total 62 articles about Cyclohexanone, 2-amino-2-(2-chlorophenyl)-6-hydroxy- 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: 85.0%

(S)-ketamine (100477-72-3,33643-46-8,33643-49-1) → (2S,6S)-2-amino-2-(2-chlorophenyl)-6-hydroxycyclohexan-1-one (120199-64-6,81395-70-2)

Guidance literature:

In water; at 25 ℃; Enzymatic reaction;

DOI:10.1021/acscatal.9b05384

Reference yield: 44.0%

tert-butyl ((1R,3S)-1-(2-chlorophenyl)-3-hydroxy-2-oxocyclohexyl)carbamate → (2R,6S)-2-amino-2-(2-chlorophenyl)-6-hydroxycyclohexan-1-one (120199-64-6,81395-70-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 0.75h;

DOI:10.1021/acs.orglett.7b02177

Reference yield: 28.0%

[(1S,3S)-1-(2-Chloro-phenyl)-2-oxo-3-trimethylsilanyloxy-cyclohexyl]-carbamic acid methyl ester (103904-71-8) → (Z)-6-hydroxynorketamine (104010-58-4,120199-64-6,81395-70-2)

Guidance literature:

With trimethylsilyl iodide; In dichloromethane; for 0.5h; Ambient temperature;

DOI:10.1021/jm00161a043

upstream raw materials:

ketamine

norketamine

2-bromo-1-chlorobenzene

cyclohexanone

Refernces

• 1、 Zheng, Zhen,Kyzer, Jillian L.,Worob, Adam,Wenthur, Cody J.. "Family of Structurally Related Bioconjugates Yields Antibodies with Differential Selectivity against Ketamine and 6-Hydroxynorketamine". . p. 4113 - 4122. Retrieved 2021/11/01.
• 2、 -. "CRYSTAL FORMS AND METHODS OF SYNTHESIS OF (2R, 6R)-HYDROXYNORKETAMINE AND (2S, 6S)-HYDROXYNORKETAMINE". . . Retrieved 2019/02/19.