AKOS BBS-00006108

Base Information

• Chemical Name: AKOS BBS-00006108
• CAS No.: 139276-14-5
• Molecular Formula: C15H9ClO3
• Molecular Weight: 272.688
• Mol file: 139276-14-5.mol

Synonyms:(Z)-6-hydroxy-2-(4-chlorobenzylidene)benzofuran-3(2H)-one;2-[1-(4-Chloro-phenyl)-meth-(Z)-ylidene]-6-hydroxy-benzofuran-3-one;2-(p-chlorobenzylidene)-6-hydroxy-3(2H)-benzofuranone;2-(4'-chlorobenzylidene)-6-hydroxybenzofuran-3(2H)-one;

Chemical Property of AKOS BBS-00006108

Chemical Property:

• PSA: 46.53000
• LogP: 3.66180

Purity/Quality:

98%min ^*data from raw suppliers

(2Z)-2-(4-Chlorobenzylidene)-6-hydroxy-1-benzofuran-3(2H)-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of AKOS BBS-00006108

There total 4 articles about AKOS BBS-00006108 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: 67.0%

6-hydroxybenzofuran-3-one (6272-26-0) + 4-chlorobenzaldehyde (104-88-1) → (Z)-6-hydroxy-2-(4-chlorobenzylidene)benzofuran-3(2H)-one (139276-14-5)

Guidance literature:

6-hydroxybenzofuran-3-one; 4-chlorobenzaldehyde; With potassium hydroxide; In methanol; water; at 60 ℃; for 1h;

With hydrogenchloride; In methanol; water;

DOI:10.1016/j.ejmech.2010.03.023

Reference yield: 58.7%

6-hydroxy-2-oxo-3H-benzofuran-2-one (2688-49-5) + 4-chlorobenzaldehyde (104-88-1) → (Z)-6-hydroxy-2-(4-chlorobenzylidene)benzofuran-3(2H)-one (139276-14-5)

Guidance literature:

With thionyl chloride; In ethanol; at 25 ℃;

DOI:10.1016/j.ejmech.2017.06.018

Reference yield:

recorcinol (108-46-3) → (Z)-6-hydroxy-2-(4-chlorobenzylidene)benzofuran-3(2H)-one (139276-14-5)

Guidance literature:

Multi-step reaction with 3 steps

1: aluminum (III) chloride / diethyl ether / 0 - 30 °C

2: sodium hydroxide / water / 30 - 50 °C

3: sodium hydroxide / water; methanol / 30 - 40 °C

With aluminum (III) chloride; sodium hydroxide; In methanol; diethyl ether; water; 1: |Friedel-Crafts Acylation / 3: |Claisen-Schmidt Condensation;

DOI:10.2174/1573406413666170623085534

upstream raw materials:

6-hydroxybenzofuran-3-one

4-chlorobenzaldehyde

6-hydroxy-2-oxo-3H-benzofuran-2-one

2-chloro-1-(2,4-dihydroxyphenyl)ethanone

Downstream raw materials:

2-(p-chlorobenzyl)-6-methoxy-3(2H)-benzofuranone

2-(p-chlorobenzyl)-3-phenyl>-6-methoxybenzofuran hydrochloride

1-(2-{4-[2-(4-Chloro-benzyl)-6-methoxy-benzofuran-3-yl]-phenoxy}-ethyl)-piperidine; hydrochloride

4-(2-{4-[2-(4-Chloro-benzyl)-6-methoxy-benzofuran-3-yl]-phenoxy}-ethyl)-morpholine; hydrochloride

Refernces

• 1、 Kadasi, Sundeep,Costa, Thadeu E.M.M.,Arukala, Neha,Toshakani, Mallika,Duggineti, Chaitanya,Thota, Sreekanth,Gupta, Sayan D.,Raj, Shiva,Penido, Carmen,Henriques, Maria G.,Raghavendra, Nulgumnalli M.. "Drug design, synthesis and in vitro evaluation of substituted benzofurans as hsp90 inhibitors". . p. 44 - 52. Retrieved 2018/02/14.
• 2、 Lee, Chong-Yew,Chew, Eng-Hui,Go, Mei-Lin. "Functionalized aurones as inducers of NAD(P)H:quinone oxidoreductase 1 that activate AhR/XRE and Nrf2/ARE signaling pathways: Synthesis, evaluation and SAR". experimental part. p. 2957 - 2971. Retrieved 2010/09/03.