(1R,3R,4S,5R,S_S)-4,6,6-trimethyl-3-(phenylsulfoxy)bicyclo<3.1.1>heptan-2-one

Base Information

• Chemical Name: (1R,3R,4S,5R,S_S)-4,6,6-trimethyl-3-(phenylsulfoxy)bicyclo<3.1.1>heptan-2-one
• CAS No.: 214827-18-6
• Molecular Formula: C₁₆H₂₀O₂S
• Molecular Weight: 276.4
• Mol file: 214827-18-6.mol

Synonyms:(1R,3R,4S,5R,S_S)-4,6,6-trimethyl-3-(phenylsulfoxy)bicyclo<3.1.1>heptan-2-one

Chemical Property of (1R,3R,4S,5R,S_S)-4,6,6-trimethyl-3-(phenylsulfoxy)bicyclo<3.1.1>heptan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3R,4S,5R,S_S)-4,6,6-trimethyl-3-(phenylsulfoxy)bicyclo<3.1.1>heptan-2-one

There total 11 articles about (1R,3R,4S,5R,S_S)-4,6,6-trimethyl-3-(phenylsulfoxy)bicyclo<3.1.1>heptan-2-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: 85.0%

(1R,3RS,4S,5R)-4,6,6-Trimethyl-3-(phenylthio)bicyclo<3.1.1>heptan-2-one (128261-65-4,128261-70-1) → (1R,3R,4S,5R,SS)-4,6,6-trimethyl-3-(phenylsulfoxy)bicyclo<3.1.1>heptan-2-one (214827-18-6) + (1R,3R,4S,5R,RS)-4,6,6-trimethyl-3-(phenylsulfoxy)bicyclo<3.1.1>heptan-2-one (214827-21-1)

Guidance literature:

With sodium periodate; In methanol; water; at 0 ℃; for 24h;

DOI:10.1021/jo9807316

Reference yield: 67.0%

(1R,3R,4S,5R)-4,6,6-trimethyl-3-(phenylthio)bicyclo<3.1.1>heptan-2-one (128261-70-1) → (1R,3R,4S,5R,SS)-4,6,6-trimethyl-3-(phenylsulfoxy)bicyclo<3.1.1>heptan-2-one (214827-18-6) + (1R,3R,4S,5R,RS)-4,6,6-trimethyl-3-(phenylsulfoxy)bicyclo<3.1.1>heptan-2-one (214827-21-1)

Guidance literature:

With sodium periodate; In methanol; water; at 0 ℃; for 24h;

DOI:10.1021/jo9807316

Reference yield:

(1R,5S)-(+)-nopinone (38651-65-9) → (1R,3R,4S,5R,SS)-4,6,6-trimethyl-3-(phenylsulfoxy)bicyclo<3.1.1>heptan-2-one (214827-18-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 14 percent / LDA / tetrahydrofuran

2: 63 percent / NaIO₄ / H₂O; methanol / 24 h / 0 °C

3: 93 percent / K₂CO₃ / toluene / 120 °C

4: 1.) CuI / 1.) ether, 1 h, 2.) ether, 2 h

5: 1.) diisopropylamine, BuLi / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, -78 deg C to room temp., 6 h

6: 67 percent / NaIO₄ / H₂O; methanol / 24 h / 0 °C

With sodium periodate; copper(l) iodide; n-butyllithium; potassium carbonate; diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; water; toluene;

DOI:10.1021/jo9807316

upstream raw materials:

(1R,3RS,4S,5R)-4,6,6-Trimethyl-3-(phenylthio)bicyclo<3.1.1>heptan-2-one

(1R,3R,4S,5R)-4,6,6-trimethyl-3-(phenylthio)bicyclo<3.1.1>heptan-2-one

S-Phenyl benzenethiosulfonate

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

Downstream raw materials:

Verbenone