(1S,3R)-3-(2-hydroxy-4-methylphenyl)-1,3-dimethyl-2-methylidenecyclopentanol

Base Information

• Chemical Name: (1S,3R)-3-(2-hydroxy-4-methylphenyl)-1,3-dimethyl-2-methylidenecyclopentanol
• CAS No.: 154699-13-5
• Molecular Formula: C₁₅H₂₀O₂
• Molecular Weight: 232.323
• Mol file: 154699-13-5.mol

Synonyms:(1S,3R)-3-(2-hydroxy-4-methylphenyl)-1,3-dimethyl-2-methylidenecyclopentanol

Chemical Property of (1S,3R)-3-(2-hydroxy-4-methylphenyl)-1,3-dimethyl-2-methylidenecyclopentanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3R)-3-(2-hydroxy-4-methylphenyl)-1,3-dimethyl-2-methylidenecyclopentanol

There total 2 articles about (1S,3R)-3-(2-hydroxy-4-methylphenyl)-1,3-dimethyl-2-methylidenecyclopentanol 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: 88.0%

(3R)-3-<2-(tert-Butyldimethylsiloxy)-4-methylphenyl>-1,3-dimethyl-2-methylidenecyclopentanol → (1S,3R)-3-(2-hydroxy-4-methylphenyl)-1,3-dimethyl-2-methylidenecyclopentanol (154699-13-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1021/jo00080a014

Reference yield: 40.0%

(1S,3R)-3-(2-methoxymethoxy-4-methylphenyl)-1,3-di-methyl-2-methylenecyclopentanol (1236304-80-5) → (1S,3R)-3-(2-hydroxy-4-methylphenyl)-1,3-dimethyl-2-methylidenecyclopentanol (154699-13-5)

Guidance literature:

With hydrogenchloride; water; In isopropyl alcohol; at 0 ℃; for 30h;

DOI:10.1016/j.tet.2010.04.134

Reference yield:

(1S,3R)-3-(2-hydroxy-4-methylphenyl)-1,3-dimethyl-2-methylidenecyclopentanol (154699-13-5) → (-)-Aplysin (6790-63-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 88 percent / Hg(OCOCF₃)2 / tetrahydrofuran / 2 h / Ambient temperature

2: 100 percent / POCl₃, pyridine / 18 h / Ambient temperature

3: 79 percent / H₂ / PtO₂ / ethanol / 3 h / Ambient temperature

4: 84 percent / NaHCO₃, Br₂ / CHCl₃ / 0.17 h / Ambient temperature

With pyridine; hydrogen; bromine; mercury(II) trifluoroacetate; sodium hydrogencarbonate; trichlorophosphate; platinum(IV) oxide; In tetrahydrofuran; ethanol; chloroform;

DOI:10.1021/jo00080a014

upstream raw materials:

(1S,3R)-3-(2-methoxymethoxy-4-methylphenyl)-1,3-di-methyl-2-methylenecyclopentanol

Downstream raw materials:

(-)-Debromoaplysin

(-)-Aplysin