13-Methyl-17-norabieta-7,15-diene

Base Information

• Chemical Name: 13-Methyl-17-norabieta-7,15-diene
• CAS No.: 1686-66-4
• Molecular Formula: C₂₀H₃₂
• Molecular Weight: 272.474
• Mol file: 1686-66-4.mol

Synonyms:Phenanthrene,7-ethenyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydro-1,1,4a,7-tetramethyl-,[4aS-(4aa,4bb,7b,10ab)]-; Podocarp-7-ene, 13b-methyl-13-vinyl- (7CI,8CI);Isopimara-7,15-diene; Isopimaradiene

Chemical Property of 13-Methyl-17-norabieta-7,15-diene

Chemical Property:

• PSA: 0.00000
• LogP: 6.14150

Purity/Quality:

98.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 13-Methyl-17-norabieta-7,15-diene

There total 18 articles about 13-Methyl-17-norabieta-7,15-diene 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%

cis-4a-cisoid-4a,4b-trans-4b-perhydro-2α,4bβ,8,8-tetramethyl-2β-vinylphenanthrene-10α-ol (82521-53-7,91599-27-8,124511-38-2) → cisoid-4a,4b-trans-4b-1,2,3,4,5,6,7,8,8a,9-dodecahydro-2α,4bβ,8,8-tetramethyl-2β-vinylphenanthrene (9βH-pimara-7,19-diene) (1686-66-4,21561-91-1,34232-20-7,68556-53-6,107541-02-6,107713-21-3,107983-51-7,124511-39-3,140147-41-7)

Guidance literature:

With trichlorophosphate; In pyridine; at 0 ℃; for 0.166667h;

DOI:10.1016/S0040-4020(01)80107-1

Reference yield:

(2S,4aS,4bR,8R,8aR)-2,4b,8-Trimethyl-8-phenylsulfanylmethyl-2-vinyl-1,2,3,4,4a,4b,5,6,7,8,8a,9-dodecahydro-phenanthrene (142699-20-5,142699-21-6) → isopimara-7,15-diene (1686-66-4)

Guidance literature:

With lithium-sodium alloy; ammonia; In tetrahydrofuran; at -33 ℃; for 1h;

DOI:10.1021/jo00043a013

Reference yield:

(E,E,E)-geranylgeranyl diphosphate (6699-20-3,13100-78-2,64732-91-8) → isopimara-7,15-diene (1686-66-4)

Guidance literature:

With recombinant cyclase from A_. fumigatus; In aq. phosphate buffer; at 16 ℃; for 72h; pH=7; Reagent/catalyst; Enzymatic reaction;

DOI:10.1021/acs.jnatprod.6b00764

upstream raw materials:

Isopimar-15-en-7-one

(2S,4aS,4bR,8R,8aR)-2,4b,8-Trimethyl-8-phenylsulfanylmethyl-2-vinyl-1,2,3,4,4a,4b,5,6,7,8,8a,9-dodecahydro-phenanthrene

pimara-7,15-dien-18-ol

isopimaric acid

Refernces

• 1、 Zhou, Ke,Xu, Meimei,Tiernan, Mollie,Xie, Qian,Peters, Reuben J.,Toyomasu, Tomonobu,Sugawara, Chizu,Oku, Madoka,Usui, Masami,Mitsuhashi, Wataru,Chono, Makiko,Chandler, Peter M.. "Functional characterization of wheat ent-kaurene(-like) synthases indicates continuing evolution of labdane-related diterpenoid metabolism in the cereals". . p. 47 - 55,9. Retrieved 2012/12/12.
• 2、 Chu, Min,Coates, Robert M.. "Partial Synthesis of 9,10-Syn Diterpenes via Tosylhydrazone Reduction: (-)-(9β)-Pimara-7,15-diene and (-)-(9β)-Isopimaradiene". . p. 4590 - 4597. Retrieved 2007/10/02.