3-Phenyl-2,4,10-trioxa-adamantane

Base Information

• Chemical Name: 3-Phenyl-2,4,10-trioxa-adamantane
• CAS No.: 74091-54-6
• Molecular Formula: C₁₃H₁₄O₃
• Molecular Weight: 218.252
• Mol file: 74091-54-6.mol

Synonyms:3-Phenyl-2,4,10-trioxa-adamantane

Chemical Property of 3-Phenyl-2,4,10-trioxa-adamantane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Phenyl-2,4,10-trioxa-adamantane

There total 2 articles about 3-Phenyl-2,4,10-trioxa-adamantane 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: 100.0%

cis,cis-1,3,5-trihydroxycyclohexane (50409-12-6,13314-30-2) + orthobenzoic acid trimethyl ester (707-07-3) → 3-Phenyl-2,4,10-trioxa-adamantane (74091-54-6)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃;

DOI:10.1248/cpb.48.1545

Reference yield:

N-methyl-N-phenyl-benzamide (1934-92-5) → 3-Phenyl-2,4,10-trioxa-adamantane (74091-54-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dichloromethane / 20 h / 20 °C

1.2: 0.17 h / 20 °C

1.3: 0.25 h / 20 °C

2.1: boron trifluoride diethyl etherate / dichloromethane / 20 °C / Inert atmosphere

With boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1021/acs.joc.9b00108

Reference yield: 70.0%

3-Phenyl-2,4,10-trioxa-adamantane (74091-54-6) → cis-3,5-O-benzylidenecyclohexanol (310904-10-0)

Guidance literature:

With borane-THF; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -15 ℃; for 60h;

DOI:10.1248/cpb.48.1545

upstream raw materials:

cis,cis-1,3,5-trihydroxycyclohexane

orthobenzoic acid trimethyl ester

N-methyl-N-phenyl-benzamide

Downstream raw materials:

Benzoic acid (1S,3R,5S)-3,5-dihydroxy-cyclohexyl ester

cis-3,5-O-benzylidenecyclohexanol

3,5-O-benzylidenecyclohexanone

(3R,5S)-3,5-O-benzylidene-6-oxohexanoic acid

Refernces

• 1、 Honda,Endo,Ono. "Construction of an enantiomerically pure 6-substituted 3,5-syn-dihydroxyhexanoic acid system by an enantioselective deprotonation strategy: Formal synthesis of an antiobesity agent, (-)-tetrahydrolipstatin". . p. 1545 - 1548. Retrieved 2007/10/03.
• 2、 Bouab, Otmane,Lamaty, Gerard,Moreau, Claude,Pomares, Odile,Deslongchamps, Pierre,Ruest, Luc. "Acid catalysed hydrolysis of orthoesters: mechanism of hydrolysis of 2,4,10-trioxaadamantanes substituted in position 3". . p. 567 - 573. Retrieved 2007/10/02.