2,2-DIMETHYL-PROPIONIC ACID (1R,5S)-6,6-DIMETHYL-BICYCLO[3.1.1]HEPT-2-EN-2-YLMETHYL ESTER

Base Information

• Chemical Name: 2,2-DIMETHYL-PROPIONIC ACID (1R,5S)-6,6-DIMETHYL-BICYCLO[3.1.1]HEPT-2-EN-2-YLMETHYL ESTER
• CAS No.: 76163-95-6
• Molecular Formula: C15H24 O2
• Molecular Weight: 236.354
• Hs Code.: 2915900090
• Mol file: 76163-95-6.mol

Synonyms:Propanoicacid, 2,2-dimethyl-, (6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl ester,(1R)-

Chemical Property of 2,2-DIMETHYL-PROPIONIC ACID (1R,5S)-6,6-DIMETHYL-BICYCLO[3.1.1]HEPT-2-EN-2-YLMETHYL ESTER

Chemical Property:

• PSA: 26.30000
• LogP: 3.56810
• Storage Temp.: Refrigerator
• Solubility.: Dichloromethane, Ethyl Acetate, Methanol, Hexanes

Purity/Quality:

98% ^*data from raw suppliers

MyrtenolPivalate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,2-DIMETHYL-PROPIONIC ACID (1R,5S)-6,6-DIMETHYL-BICYCLO[3.1.1]HEPT-2-EN-2-YLMETHYL ESTER

There total 1 articles about 2,2-DIMETHYL-PROPIONIC ACID (1R,5S)-6,6-DIMETHYL-BICYCLO[3.1.1]HEPT-2-EN-2-YLMETHYL ESTER 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: 91.0%

(1R)-Myrtenol (19894-97-4) + pivaloyl chloride (3282-30-2) → (1R,5S)-2-[(2,2-dimethylpropoyloxy)methyl]-6,6-dimethylbicyclo[3.1.1]hept-2-ene (76163-95-6)

Guidance literature:

With pyridine; at 20 ℃; Cooling with ice;

Reference yield: 55.0%

(1R,5S)-2-[(2,2-dimethylpropoyloxy)methyl]-6,6-dimethylbicyclo[3.1.1]hept-2-ene (76163-95-6) → (1S,5R)-4-[(2,2-dimethylpropoyloxy)methyl]-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-one (76163-96-7)

Guidance literature:

(1R,5S)-2-[(2,2-dimethylpropoyloxy)methyl]-6,6-dimethylbicyclo[3.1.1]hept-2-ene; With 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; In dichloromethane; at -20 ℃; for 4h; Inert atmosphere;

With sodium hydroxide; In dichloromethane; water; at -20 - 0 ℃; for 1h; Inert atmosphere;

Reference yield:

(1R,5S)-2-[(2,2-dimethylpropoyloxy)methyl]-6,6-dimethylbicyclo[3.1.1]hept-2-ene (76163-95-6) → dexanabinol (112924-45-5,137428-19-4,112830-95-2)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium chromate / acetic acid; acetic anhydride / 72 h / 35 °C

2: lithium tri-tert-butoxyaluminohydride / tetrahydrofuran

3: boron trifluoride etherate / CH₂Cl₂ / -20 °C

4: lithium aluminum hydride

With lithium aluminium tetrahydride; sodium chromate(VI); lithium tri(t-butoxy)aluminum hydride; boron trifluoride diethyl etherate; In tetrahydrofuran; dichloromethane; acetic anhydride; acetic acid;

DOI:10.1016/S0957-4166(00)86322-3

upstream raw materials:

(1R)-Myrtenol

pivaloyl chloride

Downstream raw materials:

2,2-Dimethyl-propionic acid (1R,5R)-6,6-dimethyl-4-oxo-bicyclo[3.1.1]hept-2-en-2-ylmethyl ester

(1S,5R)-4-[(2,2-dimethylpropoyloxy)methyl]-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-one

(1S,5R)-4-[(2,2-dimethylpropoyloxy)methyl]-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-ol

2,2-Dimethyl-propionic acid (1R,5R)-4-hydroxy-6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-ylmethyl ester

Refernces

• 1、 -. "Cannabinoid compound as well as preparation method, composition and application thereof". Paragraph 0243-0246. . Retrieved 2020/12/30.
• 2、 -. "COMPOSITIONS COMPRISING CB RECEPTOR AGONISTS, USES THEREOF AND METHODS FOR THEIR PREPARATION". Page/Page column 20. . Retrieved 2010/04/28.