(+/-)-cis-2--1-<2-(1,3-benzodioxol-5-yl)ethynyl>cyclopentanol

Base Information

• Chemical Name: (+/-)-cis-2--1-<2-(1,3-benzodioxol-5-yl)ethynyl>cyclopentanol
• CAS No.: 135191-26-3
• Molecular Formula: C₂₃H₂₂N₂O₃
• Molecular Weight: 374.439
• Mol file: 135191-26-3.mol

Synonyms:

Chemical Property of (+/-)-cis-2--1-<2-(1,3-benzodioxol-5-yl)ethynyl>cyclopentanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-cis-2--1-<2-(1,3-benzodioxol-5-yl)ethynyl>cyclopentanol

There total 8 articles about (+/-)-cis-2--1-<2-(1,3-benzodioxol-5-yl)ethynyl>cyclopentanol 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: 92.0%

C9H5CeCl2O2 + (+/-)-2-cyclopentanone (83196-16-1) → (+/-)-cis-2--1-<2-(1,3-benzodioxol-5-yl)ethynyl>cyclopentanol (135191-26-3,150357-70-3)

Guidance literature:

In tetrahydrofuran; at -78 ℃;

DOI:10.1021/jo00017a002

Reference yield:

piperonal (120-57-0,30024-74-9) → (+/-)-cis-2--1-<2-(1,3-benzodioxol-5-yl)ethynyl>cyclopentanol (135191-26-3,150357-70-3)

Guidance literature:

Multi-step reaction with 3 steps

1: Zn, PPh₃ / CH₂Cl₂ / 5 h / 23 °C

2: n-BuLi / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -78 deg C -> 23 deg C, 30 min, 3.) 23 deg C, 1 h

3: 1.) CeCl₃, n-BuLi / 1.) THF, -78 deg C, 1 h, 2.) THF, 6 h

With n-butyllithium; cerium(III) chloride; triphenylphosphine; zinc; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00069a032

Reference yield:

(+/-)-trans-2-bromocyclopentanol (28435-62-3,74305-04-7,87014-72-0,122673-88-5,122673-92-1,20377-79-1) → (+/-)-cis-2--1-<2-(1,3-benzodioxol-5-yl)ethynyl>cyclopentanol (135191-26-3,150357-70-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / 12 h / 100 °C

2: 89 percent / conc. HCl / acetone / 18 h / Ambient temperature

3: 88 percent / oxalylchloride, Me₂SO, Et₃N / CH₂Cl₂ / -78 °C

4: 1.) CeCl₃, n-BuLi / 1.) THF, -78 deg C, 1 h, 2.) THF, 6 h

With hydrogenchloride; n-butyllithium; cerium(III) chloride; Chloro-oxo-acetic acid; dimethyl sulfoxide; triethylamine; In dichloromethane; acetone;

DOI:10.1021/jo00069a032

upstream raw materials:

3,4-methylenedioxyphenylethyne

(+/-)-2-cyclopentanone

piperonal

(+/-)-trans-2-bromocyclopentanol

Downstream raw materials:

(+/-)-cis-2-(N-Benzylamino)-1-<2-(1,3-benzodioxol-5-yl)ethynyl>cyclopentanol

(+/-)-pancracine

(+/-)-(3R*,3aS*,7aS*)-N-Benzyl-3-(1,3-benzodioxol-5-yl)-4-oxooctahydroindole

(+/-)-cis-2-N-Benzyl-6a<(E)-2-(1,3-benzodioxol-5-yl)ethenyl>-1-oxa-3-azabicyclo<3.3.0>octane