(1R,2R,3R,6R,7S,9R)-9-Phenoxymethyl-4-oxa-tricyclo[4.2.1.0^3,7]nonan-2-ol

Base Information

• Chemical Name: (1R,2R,3R,6R,7S,9R)-9-Phenoxymethyl-4-oxa-tricyclo[4.2.1.0^3,7]nonan-2-ol
• CAS No.: 141602-69-9
• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.306
• Mol file: 141602-69-9.mol

Synonyms:(1R,2R,3R,6R,7S,9R)-9-Phenoxymethyl-4-oxa-tricyclo[4.2.1.0^3,7]nonan-2-ol

Chemical Property of (1R,2R,3R,6R,7S,9R)-9-Phenoxymethyl-4-oxa-tricyclo[4.2.1.0^3,7]nonan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,3R,6R,7S,9R)-9-Phenoxymethyl-4-oxa-tricyclo[4.2.1.0^3,7]nonan-2-ol

There total 3 articles about (1R,2R,3R,6R,7S,9R)-9-Phenoxymethyl-4-oxa-tricyclo[4.2.1.0^3,7]nonan-2-ol 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: 70.0%

Toluene-4-sulfonic acid (1R,2R,3R,6R,7S,9R)-2-hydroxy-4-oxa-tricyclo[4.2.1.03,7]non-9-ylmethyl ester (89502-67-0,96243-76-4) + phenol (108-95-2,27073-41-2) → (1R,2R,3R,6R,7S,9R)-9-Phenoxymethyl-4-oxa-tricyclo[4.2.1.03,7]nonan-2-ol (141602-69-9)

Guidance literature:

With potassium hydroxide; In dimethyl sulfoxide; for 12h;

DOI:10.1039/C39920000419

Reference yield:

(+/-)-(2-endo,3-exo)-bicyclo[2.2.1]hept-5-eno-2,3-dimethanol (699-96-7,448922-61-0) → (1R,2R,3R,6R,7S,9R)-9-Phenoxymethyl-4-oxa-tricyclo[4.2.1.03,7]nonan-2-ol (141602-69-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / 3-chloroperbenzoic acid (3-CPBA) / CH₂Cl₂ / 12 h / 0 - 20 °C

2: pyridine / 10 h / 0 °C

3: 70 percent / KOH / dimethylsulfoxide / 12 h

With pyridine; potassium hydroxide; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; dimethyl sulfoxide;

DOI:10.1039/C39920000419

Reference yield:

(1R,2R,3R,6R,7S,9R)-9-Hydroxymethyl-4-oxa-tricyclo[4.2.1.03,7]nonan-2-ol (102228-27-3,141661-18-9) → (1R,2R,3R,6R,7S,9R)-9-Phenoxymethyl-4-oxa-tricyclo[4.2.1.03,7]nonan-2-ol (141602-69-9)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 10 h / 0 °C

2: 70 percent / KOH / dimethylsulfoxide / 12 h

With pyridine; potassium hydroxide; In dimethyl sulfoxide;

DOI:10.1039/C39920000419

upstream raw materials:

Toluene-4-sulfonic acid (1R,2R,3R,6R,7S,9R)-2-hydroxy-4-oxa-tricyclo[4.2.1.0^3,7]non-9-ylmethyl ester

phenol

(+/-)-(2-endo,3-exo)-bicyclo[2.2.1]hept-5-eno-2,3-dimethanol

(1R,2R,3R,6R,7S,9R)-9-Hydroxymethyl-4-oxa-tricyclo[4.2.1.0^3,7]nonan-2-ol

Downstream raw materials:

(4aS,7S,7aS)-7-Phenoxymethyl-4,4a,7,7a-tetrahydro-1H-cyclopenta[c]pyran-3-one

(1R,4R,5S,6R)-5-Hydroxymethyl-6-phenoxymethyl-bicyclo[2.2.1]heptan-2-one

(4aS,7S,7aS)-7-Phenoxymethyl-1,3,4,4a,7,7a-hexahydro-cyclopenta[c]pyran-3-ol