cis-1,3,4,8b-Tetrahydro-4a(2H)-biphenylenol

Base Information

• Chemical Name: cis-1,3,4,8b-Tetrahydro-4a(2H)-biphenylenol
• CAS No.: 54881-56-0
• Molecular Formula: C₁₂H₁₄O
• Molecular Weight: 174.243
• DSSTox Substance ID: DTXSID20970216
• Nikkaji Number: J3.536.940F
• Mol file: 54881-56-0.mol

Synonyms:cis-1,3,4,8b-Tetrahydro-4a(2H)-biphenylenol;2,3,4,8b-tetrahydro-1H-biphenylen-4a-ol;54881-56-0;31274-15-4;4a(2H)-Biphenylenol, 1,3,4,8b-tetrahydro-;4a(2H)-Biphenylenol, 1,3,4,8b-tetrahydro-, cis-;DTXSID20970216;AKOS004907528;LS-44375;1,3,4,8b-Tetrahydrobiphenylen-4a(2H)-ol;1,2,3,4,4a,8b-Hexahydrobiphenylene-4a-ol;J3.536.940F

Chemical Property of cis-1,3,4,8b-Tetrahydro-4a(2H)-biphenylenol

Chemical Property:

• Melting Point: 106-108 °C
• Boiling Point: 310.0±21.0 °C(Predicted)
• PKA: 14.05±0.20(Predicted)
• Density: 1.205±0.06 g/cm3(Predicted)
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 174.104465066
• Heavy Atom Count: 13
• Complexity: 213

Purity/Quality:

CIS-1,3,4,8BETA-TETRAHYDRO-4A(2H)-BIPHENYLENOL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CCC2(C(C1)C3=CC=CC=C32)O

Technology Process of cis-1,3,4,8b-Tetrahydro-4a(2H)-biphenylenol

There total 3 articles about cis-1,3,4,8b-Tetrahydro-4a(2H)-biphenylenol 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: 80.0%

iodobenzene (591-50-4) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → 1,3,4,8b-tetrahydrobiphenylen-4a(2H)-ol (31274-15-4,54881-56-0)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 5h; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.9b03652

Reference yield: 55.0%

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → (RS)-2-phenylcyclohexanone (1444-65-1) + 1,3,4,8b-tetrahydrobiphenylen-4a(2H)-ol (31274-15-4,54881-56-0)

Guidance literature:

cyclohexanone; With tetramethylpiperidine; tert.-butyl lithium; In tetrahydrofuran; hexane; at -40 ℃;

halobenzene; In tetrahydrofuran; hexane; at -40 ℃; for 5h;

DOI:10.1139/v03-099

Reference yield:

bromobenzene (108-86-1,52753-63-6) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → 1,3,4,8b-tetrahydrobiphenylen-4a(2H)-ol (31274-15-4,54881-56-0)

Guidance literature:

With sodium amide;

upstream raw materials:

bromobenzene

cyclohexanone

iodobenzene

Downstream raw materials:

(RS)-2-phenylcyclohexanone

7,8,9,10-tetrahydro-6H-benzocycloocten-5-one

1,2,3,4-tetrahydrocarbazole

5-benzoylvaleric acid

Refernces

• 1、 Rosa, David,Chtchemelinine, Andrei,Orellana, Arturo. "Tandem decarboxylative allylation and fragmentation of allyl benzocyclobutenyl carbonates: Access to ortho-functionalized aryls from aryl bromides". experimental part. p. 1885 - 1891. Retrieved 2012/08/14.
• 2、 Adam, G.,Andrieux, J.,Plat, M. "DECOMPOSITION ACIDO-CATALYSEE D'AZIDES TERTIAIRES BENZOCYCLOBUTENIQUES. NOUVELLE METHODE DE SYNTHESE DU NOYAU INDOLIQUE PAR EXTENSION DU CYCLE". . p. 399 - 408. Retrieved 2007/10/02.