(1R,5S)-6-Benzhydrylidene-bicyclo[3.2.1]octane

Base Information

• Chemical Name: (1R,5S)-6-Benzhydrylidene-bicyclo[3.2.1]octane
• CAS No.: 41977-09-7
• Molecular Formula: C₂₁H₂₂
• Molecular Weight: 274.406
• Mol file: 41977-09-7.mol

Synonyms:

Chemical Property of (1R,5S)-6-Benzhydrylidene-bicyclo[3.2.1]octane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,5S)-6-Benzhydrylidene-bicyclo[3.2.1]octane

There total 11 articles about (1R,5S)-6-Benzhydrylidene-bicyclo[3.2.1]octane 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:

(1R,5S,6R)-Bicyclo[3.2.1]oct-6-yl-diphenyl-methanol → 6-(Diphenylmethylen)bicyclo<3.2.1>octan (41977-09-7)

Guidance literature:

With toluene-4-sulfonic acid; calcium chloride;

DOI:10.1021/ja00793a054

Reference yield:

(3S)-5-Oxatricyclo<4.3.1.03,8>decan-4-one (30244-07-6,91739-64-9) → (1R,5S)-6-Benzhydrylidene-bicyclo[3.2.1]octane (41977-09-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 78 percent / Sodium periodate,sodium hydroxide / Ruthenium dioxide hydrate / H₂O

2: 74 percent / Hydrazine hydrate 85percent,sodium hydroxide / bis-(2-hydroxy-ethyl) ether / 1) reflux 1h 2) 200-210 degC

3: 99 percent / diethyl ether

4: 72 percent / diethyl ether / 1)10 min. 0 degC 2) 45 min room temp.

5: 0.51 g / Anhydrous calcium chloride,p-toluenesulfonic acid / benzene / 1.5 h / Heating

With sodium hydroxide; sodium periodate; toluene-4-sulfonic acid; hydrazine hydrate; calcium chloride; ruthenium(IV) oxide; In diethyl ether; water; diethylene glycol; benzene;

Reference yield:

(2R)-endo-Bicyclo<2.2.2>oct-5-ene-2-carboxylic Acid (20507-56-6) → (1R,5S)-6-Benzhydrylidene-bicyclo[3.2.1]octane (41977-09-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 900 mg / sulfuric acid 96percent / 0.08 h / 20 °C

2: 78 percent / Sodium periodate,sodium hydroxide / Ruthenium dioxide hydrate / H₂O

3: 74 percent / Hydrazine hydrate 85percent,sodium hydroxide / bis-(2-hydroxy-ethyl) ether / 1) reflux 1h 2) 200-210 degC

4: 99 percent / diethyl ether

5: 72 percent / diethyl ether / 1)10 min. 0 degC 2) 45 min room temp.

6: 0.51 g / Anhydrous calcium chloride,p-toluenesulfonic acid / benzene / 1.5 h / Heating

With sodium hydroxide; sodium periodate; sulfuric acid; toluene-4-sulfonic acid; hydrazine hydrate; calcium chloride; ruthenium(IV) oxide; In diethyl ether; water; diethylene glycol; benzene;

upstream raw materials:

methyl bicyclo<3.2.1>octane-6α-carboxylate

3(a)-Hydroxy-bicyclo<3.2.1>octan-6-endo-carbonsaeure-γ-lacton

(3S)-5-Oxatricyclo<4.3.1.0^3,8>decan-4-one

(1R,5S)-Bicyclo[3.2.1]octane-6-carboxylic acid

Downstream raw materials:

(1R,5S)-Bicyclo[3.2.1]octan-6-one

bicyclo[3.2.1]octan-6-one

Refernces

• 1、 Tichy, Milos,Farag, Ahmed,Budesinsky, Milos,Otroschenko, Ludmila P.,Shibanova, Tatjana A.,Blaha, Karel. "ISOMERIC OXATRICYCLODECANONES WITH NON-PLANAR LACTONE GROUPS: SYNTHESIS,ABSOLUTE CONFIGURATION,NMR AND X-RAY STUDY". . p. 513 - 532. Retrieved 2007/10/02.