(+/-)-(Z)-3-(2-cyclohexylidene-ethylidene)-t-5-methoxymethoxy-4-methylenecyclohexan-r-1-ol

Base Information

• Chemical Name: (+/-)-(Z)-3-(2-cyclohexylidene-ethylidene)-t-5-methoxymethoxy-4-methylenecyclohexan-r-1-ol
• CAS No.: 88908-94-5
• Molecular Formula: C₁₇H₂₆O₃
• Molecular Weight: 278.392
• Mol file: 88908-94-5.mol

Synonyms:(+/-)-(Z)-3-(2-cyclohexylidene-ethylidene)-t-5-methoxymethoxy-4-methylenecyclohexan-r-1-ol

Chemical Property of (+/-)-(Z)-3-(2-cyclohexylidene-ethylidene)-t-5-methoxymethoxy-4-methylenecyclohexan-r-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-(Z)-3-(2-cyclohexylidene-ethylidene)-t-5-methoxymethoxy-4-methylenecyclohexan-r-1-ol

There total 13 articles about (+/-)-(Z)-3-(2-cyclohexylidene-ethylidene)-t-5-methoxymethoxy-4-methylenecyclohexan-r-1-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: 65.3%

(+/-)-2-hydroxy-2-<(3β-methoxymethoxy-2-methylenebicyclo<3.1.0>hexane)-1>ethylidenecyclohexane (88908-93-4,88979-90-2,98758-87-3) → (+/-)-(Z)-3-(2-cyclohexylidene-ethylidene)-t-5-methoxymethoxy-4-methylenecyclohexan-r-1-ol (88908-94-5)

Guidance literature:

toluene-4-sulfonic acid; In 1,4-dioxane; water; at 55 ℃; for 0.166667h;

DOI:10.1016/S0040-4039(00)88315-X

Reference yield: 65.3%

(+/-)-α-cyclohexylidenemethyl-3-methoxymethoxy-2-methylenebicyclo<3.1.0>hexane-1-methanol (98758-87-3) → (+/-)-(Z)-3-(2-cyclohexylidene-ethylidene)-t-5-methoxymethoxy-4-methylenecyclohexan-r-1-ol (88908-94-5)

Guidance literature:

With toluene-4-sulfonic acid; In 1,4-dioxane; water; at 50 ℃; for 0.166667h;

Reference yield:

2-oxo-bicyclo[3.1.0]hexane-1-carboxylic acid methyl ester (61996-11-0) → (+/-)-(Z)-3-(2-cyclohexylidene-ethylidene)-t-5-methoxymethoxy-4-methylenecyclohexan-r-1-ol (88908-94-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 47 percent / BuLi / tetrahydrofuran

2: 41.3 percent / SeO₂, tert-butyl hydroperoxide / CH₂Cl₂ / 3 h / Ambient temperature

3: 96 percent / diisopropylethylamine

4: 83.4 percent / LiAlH₄

5: 71 percent / pyridinium chlorochromate / CH₂Cl₂

6: 1) n-butyllithium / 1) THF, -20 deg C, 2 h; 2) -78 deg C, 30 min

7: 65.3 percent / p-toluenesulphonic acid / dioxane; H₂O / 0.17 h / 55 °C

With tert.-butylhydroperoxide; lithium aluminium tetrahydride; n-butyllithium; selenium(IV) oxide; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; toluene-4-sulfonic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water;

DOI:10.1016/S0040-4039(00)88315-X

upstream raw materials:

(+/-)-2-hydroxy-2-<(3β-methoxymethoxy-2-methylenebicyclo<3.1.0>hexane)-1>ethylidenecyclohexane

(+/-)-α-cyclohexylidenemethyl-3-methoxymethoxy-2-methylenebicyclo<3.1.0>hexane-1-methanol

(+/-)-methyl 2-methylenebicyclo<3.1.0>hexane-1-carboxylate

(+/-)-methyl 3β-hydroxy-2-methylenebicyclo<3.1.0>hexane-1-carboxylate

Downstream raw materials:

(+/-)-(Z)-2-(3β,5α-dihydroxy-2-methylene-cyclohexylidene)ethylidenecyclohexane