4-Benzo[1,3]dioxol-5-yl-4-hydroxycyclohexanone

Base Information

• Chemical Name: 4-Benzo[1,3]dioxol-5-yl-4-hydroxycyclohexanone
• CAS No.: 150019-57-1
• Molecular Formula: C13H14O4
• Molecular Weight: 234.252
• Hs Code.: 2932999099
• Mol file: 150019-57-1.mol

Synonyms:4-(Benzo[d][1,3]dioxol-5-yl)-4-hydroxycyclohexanone;

Chemical Property of 4-Benzo[1,3]dioxol-5-yl-4-hydroxycyclohexanone

Chemical Property:

• Vapor Pressure: 1.33E-07mmHg at 25°C
• Refractive Index: 1.605
• Boiling Point: 414.2 °C at 760 mmHg
• Flash Point: 162 °C
• PSA: 55.76000
• Density: 1.348 g/cm³
• LogP: 1.74600
• Storage Temp.: 2-8°C

Purity/Quality:

NLT 98% ^*data from raw suppliers

4-(Benzo[d][1,3]dioxol-5-yl)-4-hydroxycyclohexanone 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-Benzo[1,3]dioxol-5-yl-4-hydroxycyclohexanone

There total 4 articles about 4-Benzo[1,3]dioxol-5-yl-4-hydroxycyclohexanone 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: 95.0%

8-(1,3-benzodioxol-5-yl)-1,4-dioxaspiro[4.5]decan-8-ol (150019-56-0) → 4-(1,3-benzodioxol-5-yl)-4-hydroxycyclohexanone (150019-57-1)

Guidance literature:

With hydrogenchloride; In water; acetone;

Reference yield: 20.0%

(3,4-methylenedioxy)phenylmagnesium bromide (17680-04-5) + 1,4-Cyclohexanedione (637-88-7) → 4-(1,3-benzodioxol-5-yl)-4-hydroxycyclohexanone (150019-57-1)

Guidance literature:

In tetrahydrofuran; toluene; at -78 - 20 ℃;

DOI:10.1016/j.bmcl.2010.10.020

Reference yield:

cyclohexanedione monoethylene ketal (4746-97-8) → 4-(1,3-benzodioxol-5-yl)-4-hydroxycyclohexanone (150019-57-1)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran

2: aq. HCl

With hydrogenchloride; In tetrahydrofuran;

DOI:10.1016/S0960-894X(02)00879-X

upstream raw materials:

8-(1,3-benzodioxol-5-yl)-1,4-dioxaspiro[4.5]decan-8-ol

cyclohexanedione monoethylene ketal

(3,4-methylenedioxy)phenylmagnesium bromide

1,4-Cyclohexanedione

Downstream raw materials:

N-(2-{1-[4-(benzo[d][1,3]dioxol-5-yl)-4-hydroxycyclohexyl]-4-ethoxypyrrolidin-3-ylamino}-2-oxoethyl)-3-(trifluoromethyl)benzamide

N-(2-{1-[4-(benzo[d][1,3]dioxol-5-yl)-4-hydroxycyclohexyl]-4-ethoxypyrrolidin-3-ylamino}-2-oxoethyl)-3-(trifluoromethyl)benzamide

Refernces

• 1、 Zhang, Xuqing,Hufnagel, Heather,Markotan, Thomas,Lanter, James,Cai, Chaozhong,Hou, Cuifen,Singer, Monica,Opas, Evan,McKenney, Sandra,Crysler, Carl,Johnson, Dana,Sui, Zhihua. "Overcoming hERG activity in the discovery of a series of 4-azetidinyl-1-aryl-cyclohexanes as CCR2 antagonists". supporting information; experimental part. p. 5577 - 5582. Retrieved 2011/10/09.
• 2、 Xue, Chu-Biao,Wang, Anlai,Meloni, David,Zhang, Ke,Kong, Ling,Feng, Hao,Glenn, Joseph,Huang, Taisheng,Zhang, Yingxin,Cao, Ganfeng,Anand, Rajan,Zheng, Changsheng,Xia, Michael,Han, Qi,Robinson,Storace, Lou,Shao, Lixin,Li, Mei,Brodmerkel, Carrie M.,Covington, Maryanne,Scherle, Peggy,Diamond, Sharon,Yeleswaram, Swamy,Vaddi, Kris,Newton, Robert,Hollis, Greg,Friedman, Steven,Metcalf, Brian. "Discovery of INCB3344, a potent, selective and orally bioavailable antagonist of human and murine CCR2". experimental part. p. 7473 - 7478. Retrieved 2011/01/12.