(4S,5S)-1-acetoxy-4-isopropenyl-5-methyl-5-vinyl-1-cyclohexene

Base Information

• Chemical Name: (4S,5S)-1-acetoxy-4-isopropenyl-5-methyl-5-vinyl-1-cyclohexene
• CAS No.: 128261-61-0
• Molecular Formula: C₁₄H₂₀O₂
• Molecular Weight: 220.312
• Mol file: 128261-61-0.mol

Synonyms:(4S,5S)-1-acetoxy-4-isopropenyl-5-methyl-5-vinyl-1-cyclohexene

Chemical Property of (4S,5S)-1-acetoxy-4-isopropenyl-5-methyl-5-vinyl-1-cyclohexene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-1-acetoxy-4-isopropenyl-5-methyl-5-vinyl-1-cyclohexene

There total 16 articles about (4S,5S)-1-acetoxy-4-isopropenyl-5-methyl-5-vinyl-1-cyclohexene 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: 75.0%

(1R,4S,5R)-(+)-4,6,6-trimethyl-4-vinylbicyclo<3.1.1>heptan-2-one (128261-62-1) + acetic anhydride (108-24-7) → (4S,5S)-1-acetoxy-4-isopropenyl-5-methyl-5-vinyl-1-cyclohexene (128261-61-0)

Guidance literature:

With boron trifluoride diethyl etherate; at 0 ℃; for 0.916667h; Inert atmosphere;

DOI:10.1002/anie.201610484

Reference yield: 68.0%

(1R,4S,5R)-(+)-4,6,6-trimethyl-4-vinylbicyclo<3.1.1>heptan-2-one (128261-62-1) → (4S,5S)-1-acetoxy-4-isopropenyl-5-methyl-5-vinyl-1-cyclohexene (128261-61-0)

Guidance literature:

With boron trifluoride diethyl etherate; zinc diacetate; In acetic anhydride; for 20h; Ambient temperature;

Reference yield:

(1R,5S)-(+)-nopinone (38651-65-9) → (4S,5S)-1-acetoxy-4-isopropenyl-5-methyl-5-vinyl-1-cyclohexene (128261-61-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 1) lithium diisopropylamide / 1) THF, hexane, -78 deg C, 30 min, 0 deg C, 30 min, 2) -78 deg C, 20 min, to r.t., 5 h, r.t., 15 h

2: m-CPBA / CH₂Cl₂ / 1) 0 deg C, 1 h, 2) r.t., 10 h

3: Ac₂O, methanesulfonic acid / CH₂Cl₂ / 1) 0 deg C, 1 h, 2) r.t., 15 h

4: 93 percent / CuBr*Me₂S / tetrahydrofuran / 7 h

5: m-CPBA / CH₂Cl₂ / 1) 0 deg C, 1h, 2) r.t., 10 h

6: Ac₂O, methanesulfonic acid / CH₂Cl₂ / 1) 0 deg C, 1 h, 2) r.t., 15 h

7: 93 percent / m-CPBA / CH₂Cl₂ / 1) 0 deg C, 30 min, 2) r.t., 2 h

8: 1) CuI / 1) THF, -50 deg C, 30 min, 2) -50 deg C, 1.5 h

9: 97 percent / NH₃ (liquid), Li / tetrahydrofuran / 0.5 h

10: 68 percent / BF₃*Et₂O, Zn(OAc)2 / 48 h / Ambient temperature

With copper(l) iodide; copper(I) bromide dimethylsulfide complex; methanesulfonic acid; boron trifluoride diethyl etherate; zinc diacetate; ammonia; acetic anhydride; lithium; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00025a023

upstream raw materials:

(1R,4S,5R)-(+)-4,6,6-trimethyl-4-vinylbicyclo<3.1.1>heptan-2-one

acetic anhydride

(1R,5S)-(+)-nopinone

beta-pinene

Downstream raw materials:

(4S)-trans-β-elemenone

((1R,2R,4S,5S)-2-Hydroxy-5-isopropenyl-4-methyl-4-vinyl-cyclohexyl)-acetic acid methyl ester

11β-phenylseleno-5,7,8αH-elema-1,3-dien-8,12-olide

(3S,3aS,5S,6S,7aR)-5-Isopropenyl-6-methyl-3-phenylselanyl-6-vinyl-hexahydro-benzofuran-2-one

Refernces

• 1、 Du, Biao,Yuan, Changchun,Yu, Tianzi,Yang, Li,Yang, Yang,Liu, Bo,Qin, Song. "Asymmetric total synthesis of onoseriolide, bolivianine, and isobolivianine". . p. 2613 - 2622. Retrieved 2014.
• 2、 Kato, Michiharu,Watanabe, Masataka,Vogler, Bernhard,Awen, Bahlul Z.,Masuda, Yoshiaki,et al.. "The Use of 4,4-Disubstituted Nopinones for Natural-Product Synthesis. Synthesis of Elemanoid Sesquiterpenes". . p. 7071 - 7076. Retrieved 2007/10/02.