(+)-Apoverbenone

Base Information

• Chemical Name: (+)-Apoverbenone
• CAS No.: 35408-03-8
• Molecular Formula: C9H12O
• Molecular Weight: 136.194
• European Community (EC) Number: 863-697-8
• Nikkaji Number: J437.088K
• Mol file: 35408-03-8.mol

Synonyms:(+)-Apoverbenone;35408-03-8;(1R,5R)-6,6-Dimethylbicyclo[3.1.1]hept-3-en-2-one;Bicyclo[3.1.1]hept-3-en-2-one, 6,6-dimethyl-, (1R)-;SCHEMBL2762377;NNPXUZFTLBPVNP-BQBZGAKWSA-N;EN300-344967

Chemical Property of (+)-Apoverbenone

Chemical Property:

• PSA: 17.07000
• LogP: 1.78760
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 136.088815002
• Heavy Atom Count: 10
• Complexity: 213

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(C2CC1C(=O)C=C2)C
• Isomeric SMILES: CC1([C@@H]2C[C@H]1C(=O)C=C2)C

Technology Process of (+)-Apoverbenone

There total 21 articles about (+)-Apoverbenone 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: 96.0%

(1R,3S,5R,RS)-6,6-dimethyl-3-(phenylsulfoxy)bicyclo<3.1.1>heptan-2-one (214827-15-3) → (+)-apoverbenone (35408-03-8)

Guidance literature:

With potassium carbonate; In toluene; at 120 ℃; for 4h;

DOI:10.1021/jo9807316

Reference yield: 93.0%

(1R,5R)-3-Benzenesulfinyl-6,6-dimethyl-bicyclo[3.1.1]heptan-2-one → (+)-apoverbenone (35408-03-8)

Guidance literature:

With potassium carbonate; In toluene; at 120 ℃; for 4h;

DOI:10.1021/jo9807316

Reference yield: 93.0%

(1R,3R,5R,SS)-6,6-dimethyl-3-(phenylsulfoxy)bicyclo<3.1.1>heptan-2-one (214827-20-0) → (+)-apoverbenone (35408-03-8)

Guidance literature:

With potassium carbonate; In toluene; at 120 ℃;

DOI:10.1021/jo9807316

upstream raw materials:

(-)-nopinone enol acetate

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

(1R,3S,5R)-6,6-dimethyl-3-(phenylseleno)bicyclo<3.1.1>heptan-2-one

(+)-cis-3-bromonopinone

Downstream raw materials:

(-)-4-<2,6-Dimethoxy-4-(1,1-dimethylheptyl)phenyl>-6,6-dimethylbicyclo<3.1.1>hept-3-en-2-one

4-(2-Methoxy-4-pentyl-6-(methoxymethoxy)phenyl)-6,6-dimethylbicyclo<3.1.1>hept-3-en-2-one

4-(2,6-Bis(methoxymethoxy)-4-pentylphenyl)-6,6-dimethylbicyclo<3.1.1>hept-3-en-2-one

4-(2-Methoxy-6-hydroxyphenyl)-6,6-dimethylbicyclo<3.1.1>hept-3-en-2-one

Refernces

• 1、 -. "Novel Labelled Cannabinergic Ligands and Related Analogs". Paragraph 0152; 0155. . Retrieved 2021/10/02.
• 2、 Kmieciak, Anna,Krzemiński, Marek P.. "Chiral terpene auxiliaries V: Synthesis of new chiral γ-hydroxyphosphine oxides derived from α-pinene". . p. 2493 - 2499. Retrieved 2019/12/11.