(4R,4aS,6R)-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-chloro-1-methylethyl)-2(3H)-naphthalenone

Base Information

• Chemical Name: (4R,4aS,6R)-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-chloro-1-methylethyl)-2(3H)-naphthalenone
• CAS No.: 72453-44-2
• Molecular Formula: C₁₅H₂₃ClO
• Molecular Weight: 254.8
• Mol file: 72453-44-2.mol

Synonyms:(4R,4aS,6R)-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-chloro-1-methylethyl)-2(3H)-naphthalenone

Chemical Property of (4R,4aS,6R)-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-chloro-1-methylethyl)-2(3H)-naphthalenone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (4R,4aS,6R)-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-chloro-1-methylethyl)-2(3H)-naphthalenone

There total 1 articles about (4R,4aS,6R)-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-chloro-1-methylethyl)-2(3H)-naphthalenone 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:

(1R,5S)-(+)-nopinone (38651-65-9) → (4R,4aS,6R)-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-chloro-1-methylethyl)-2(3H)-naphthalenone (72453-44-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 88 percent / triethylamine / dimethylformamide / 24 h / 95 °C

2: 96 percent / TiCl₄ / CH₂Cl₂ / 1.5 h / -78 °C

3: 90 percent / p-toluenesulfonic acid / benzene / 2 h / Heating

4: 81 percent / TiCl₄ / CH₂Cl₂

5: 71 percent / NaNH₂ / benzene

6: 1.) O₃; 2.) Zn/CH₃COOH / 1.) -78 deg C, 30 min; 2.) room temperature overnight.

7: 73 percent / HCl / acetic acid / 21 h / Ambient temperature

With hydrogenchloride; titanium tetrachloride; toluene-4-sulfonic acid; ozone; sodium amide; acetic acid; triethylamine; zinc; In dichloromethane; acetic acid; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo01292a010

Reference yield: 93.0%

(4R,4aS,6R)-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-chloro-1-methylethyl)-2(3H)-naphthalenone (72453-44-2) → (+)-nootkatone (4674-50-4)

Guidance literature:

With sodium acetate; In water; acetic acid; at 100 ℃; for 2h;

Reference yield: 81.0%

(4R,4aS,6R)-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-chloro-1-methylethyl)-2(3H)-naphthalenone (72453-44-2) → (4R,4aS)-(+)-4,4a-dimethyl-6-isopropylidene-4,4a,5,6,7,8-hexahydro-(3H)-naphthalen-2-one (15764-04-2,89-89-4)

Guidance literature:

With silica gel; In chloroform; at 60 ℃; for 27h;

DOI:10.1021/jo01292a010

upstream raw materials:

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

Downstream raw materials:

(4R,4aS)-(+)-4,4a-dimethyl-6-isopropylidene-4,4a,5,6,7,8-hexahydro-(3H)-naphthalen-2-one

(+)-nootkatone

Refernces

• 1、 Yanami, Tetsuji,Miyashita, Masaaki,Yoshikoshi, Akira. "Synthetic Study of (+)-Nootkatone from (-)-β-Pinene". . p. 607 - 612. Retrieved 2007/10/02.