1,2,3,4,4a,10b-hexahydro-6H-benzo[c]chromen-6-one

Base Information

• Chemical Name: 1,2,3,4,4a,10b-hexahydro-6H-benzo[c]chromen-6-one
• CAS No.: 6538-16-5
• Molecular Formula: C₁₃H₁₄O₂
• Molecular Weight: 202.253
• Mol file: 6538-16-5.mol

Synonyms:

Chemical Property of 1,2,3,4,4a,10b-hexahydro-6H-benzo[c]chromen-6-one

Chemical Property:

• Vapor Pressure: 3.14E-05mmHg at 25°C

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2,3,4,4a,10b-hexahydro-6H-benzo[c]chromen-6-one

There total 10 articles about 1,2,3,4,4a,10b-hexahydro-6H-benzo[c]chromen-6-one 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: 65.0%

N-quinolin-8-yl-benzamide (33757-48-1) + cyclohexane-1,2-epoxide (286-20-4) → cis-1,2,3,4,4a,10b-hexahydro-4H-dibenzopyran-6-one (72331-10-3,6538-16-5)

Guidance literature:

With nickel(II) acetate tetrahydrate; In diethylene glycol dimethyl ether; at 200 ℃; for 1h; stereospecific reaction; Sealed tube; Microwave irradiation; Inert atmosphere;

DOI:10.1002/anie.201807664

Reference yield:

cis-1,2,4a,10b-tetrahydro-4H-dibenzopyran-6-one (90992-10-2) → cis-1,2,3,4,4a,10b-hexahydro-4H-dibenzopyran-6-one (72331-10-3,6538-16-5)

Guidance literature:

With hydrogen; nickel; In ethanol; for 24h; under 3102.9 Torr;

DOI:10.1021/ja00330a041

Reference yield:

cyclohexa-1,3-diene (1165952-91-9) → cis-1,2,3,4,4a,10b-hexahydro-4H-dibenzopyran-6-one (72331-10-3,6538-16-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Tl(O₂CCF₃)3; 2.) PdCl₂, LiCl; 3.)Et₃N, Na₂CO₃

2: H₂ / Raney nickel / ethanol / 24 h / 3102.9 Torr

With hydrogen; sodium carbonate; triethylamine; lithium chloride; palladium dichloride; thallium(III) trifluoroacetate; nickel; In ethanol;

DOI:10.1021/ja00330a041

upstream raw materials:

(1R,2R)-2-phenylcyclohexanol

carbon monoxide

cis-2-phenylcyclohexanol

cis-1,2,4a,10b-tetrahydro-4H-dibenzopyran-6-one

Refernces

• 1、 Wen, Zhen-Kang,Ge, Xiao-Min,Zhao, Ze-Kai,Chao, Jian-Bin. "Palladium/Acid Relay Catalyzed Tandem Heck Coupling/6-Endo Cyclization between ortho-Halogenated Benzoates and Unactivated Terminal Alkenes for the Synthesis of 1-Isochromanones". supporting information. p. 983 - 988. Retrieved 2019/01/30.
• 2、 Larock, Richard C.,Fellows, Constance A.. "Synthesis of Aromatic Carbonyl Compounds via Thallation-Carbonylation of Arenes". . p. 1900 - 1907. Retrieved 2007/10/02.