(+/-)-4R-[4-(1,1-DIMETHYLHEPTYL)-2,6-DIMETHOXYPHENYL]-6,6-DIMETHYL-1R,5R-BICYCLO[3.1.1]HEPT-2-ENE-2-METHANOL

Base Information

• Chemical Name: (+/-)-4R-[4-(1,1-DIMETHYLHEPTYL)-2,6-DIMETHOXYPHENYL]-6,6-DIMETHYL-1R,5R-BICYCLO[3.1.1]HEPT-2-ENE-2-METHANOL
• CAS No.: 256934-39-1
• Molecular Formula: C₂₇H₄₂O₃
• Molecular Weight: 414.629
• Mol file: 256934-39-1.mol

Synonyms:HU 308;

Chemical Property of (+/-)-4R-[4-(1,1-DIMETHYLHEPTYL)-2,6-DIMETHOXYPHENYL]-6,6-DIMETHYL-1R,5R-BICYCLO[3.1.1]HEPT-2-ENE-2-METHANOL

Chemical Property:

• Boiling Point: 508.668 °C at 760 mmHg
• PKA: 14.77±0.10(Predicted)
• Flash Point: 261.433 °C
• PSA: 38.69000
• Density: 0.999 g/cm³
• LogP: 6.63000
• Storage Temp.: Store at -20°C
• Solubility.: Soluble in DMSO

Purity/Quality:

99% ^*data from raw suppliers

HU308 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A specific CB2-specific agonist that inhibits forskolin-stimulated cAMP production in CB2-transfected cells. It reduces blood pressure, blocks defecation, and elicits anti-inflammatory and peripheral analgesic activity and thus may lead to new therapies for hypertension, inflammation, and pain. Controlled Substance.

Technology Process of (+/-)-4R-[4-(1,1-DIMETHYLHEPTYL)-2,6-DIMETHOXYPHENYL]-6,6-DIMETHYL-1R,5R-BICYCLO[3.1.1]HEPT-2-ENE-2-METHANOL

There total 8 articles about (+/-)-4R-[4-(1,1-DIMETHYLHEPTYL)-2,6-DIMETHOXYPHENYL]-6,6-DIMETHYL-1R,5R-BICYCLO[3.1.1]HEPT-2-ENE-2-METHANOL 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:

2-(3-myrtenyl-pivalate)-5-dimethylheptyl dimethylresorcinol (1220887-85-3) → HU-433 (1220887-84-2,256934-39-1)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; for 2h; Reflux;

Reference yield:

myrtenol (6712-78-3) → (+)-{(1S,4S,5S)-4-[4-(1,1-dimethylheptyl)-2,6-dimethoxyphenyl]-6,6-dimethylbicyclo[3.1.1]-hept-2-en-2-yl}methanol (256934-39-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: pyridine / dichloromethane / 4 - 20 °C / Inert atmosphere

2.1: tert.-butylhydroperoxide; chromium(VI) oxide / dichloromethane / 2.5 h / 20 °C

3.1: sodium tetrahydridoborate; ethanol / 0.9 h / 20 °C / Inert atmosphere

4.1: ethanol; toluene-4-sulfonic acid / dichloromethane; toluene / 0.08 h / 35 - 40 °C / Sonication; Inert atmosphere

4.2: 0.75 h / 20 °C / Inert atmosphere

5.1: potassium carbonate / acetone / Inert atmosphere

5.2: 48 h / 20 °C / Inert atmosphere

6.1: sodium methoxide; water monomer; methanol / acetone / 48 h / 37 °C / Inert atmosphere

With pyridine; chromium(VI) oxide; methanol; tert.-butylhydroperoxide; sodium tetrahydridoborate; ethanol; water monomer; sodium methoxide; potassium carbonate; toluene-4-sulfonic acid; In dichloromethane; acetone; toluene;

Reference yield:

[(1S,5R)-4-hydroxy-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]methyl 2,2-dimethylpropanoate (926645-58-1) → (+)-{(1S,4S,5S)-4-[4-(1,1-dimethylheptyl)-2,6-dimethoxyphenyl]-6,6-dimethylbicyclo[3.1.1]-hept-2-en-2-yl}methanol (256934-39-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: ethanol; toluene-4-sulfonic acid / dichloromethane; toluene / 0.08 h / 35 - 40 °C / Sonication; Inert atmosphere

1.2: 0.75 h / 20 °C / Inert atmosphere

2.1: potassium carbonate / acetone / Inert atmosphere

2.2: 48 h / 20 °C / Inert atmosphere

3.1: sodium methoxide; water monomer; methanol / acetone / 48 h / 37 °C / Inert atmosphere

With methanol; ethanol; water monomer; sodium methoxide; potassium carbonate; toluene-4-sulfonic acid; In dichloromethane; acetone; toluene;

upstream raw materials:

[(1S,5R)-4-hydroxy-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]methyl 2,2-dimethylpropanoate

2,2-Dimethyl-propionic acid (1S,4S,5S)-4-[4-(1,1-dimethyl-heptyl)-2,6-dihydroxy-phenyl]-6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-ylmethyl ester

(+)-α-pinene

myrtenol

Refernces

• 1、 -. "COMPOSITIONS COMPRISING CB RECEPTOR AGONISTS, USES THEREOF AND METHODS FOR THEIR PREPARATION". Page/Page column 22-23. . Retrieved 2010/04/28.