AURORA 16054

Base Information

• Chemical Name: AURORA 16054
• CAS No.: 53391-77-8
• Molecular Formula: C₁₂H₉ClO₃
• Molecular Weight: 236.655
• Mol file: 53391-77-8.mol

Synonyms:

Chemical Property of AURORA 16054

Chemical Property:

Purity/Quality:

98%min ^*data from raw suppliers

8-Chloro-7-hydroxy-2,3-dihydrocyclopenta-[c]chromen-4(1H)-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of AURORA 16054

There total 4 articles about AURORA 16054 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: 73.0%

4-Chlororesorcinol (95-88-5) + 2-ethoxycarbonyl-1-cyclopentanone (611-10-9) → 8-chloro-7-hydroxy-2,3-dihydrocyclopenta[c]chromen-4(1H)-one (53391-77-8)

Guidance literature:

With sulfuric acid; In ethanol; at 0 - 20 ℃;

DOI:10.1023/B:CONC.0000003410.74701.dc

Reference yield:

4-Chlororesorcinol (95-88-5) + methyl 2-oxocyclopentane-1-carboxylate (10472-24-9,265317-94-0) → 8-chloro-7-hydroxy-2,3-dihydrocyclopenta[c]chromen-4(1H)-one (53391-77-8)

Guidance literature:

With bismuth (III) nitrate pentahydrate; at 80 ℃;

DOI:10.1016/j.ejmech.2014.01.012

Reference yield:

Adipic acid (124-04-9) → 8-chloro-7-hydroxy-2,3-dihydrocyclopenta[c]chromen-4(1H)-one (53391-77-8)

Guidance literature:

Multi-step reaction with 3 steps

1: sulfuric acid / Reflux

2: aluminum (III) chloride; triethylamine / dichloromethane / 0 - 20 °C

3: bismuth (III) nitrate pentahydrate / 80 °C

With aluminum (III) chloride; bismuth (III) nitrate pentahydrate; sulfuric acid; triethylamine; In dichloromethane; 2: |Dieckmann Condensation / 3: |Pechmann Condensation;

DOI:10.1016/j.ejmech.2014.01.012

upstream raw materials:

4-Chlororesorcinol

2-ethoxycarbonyl-1-cyclopentanone

Adipic acid

hexanedioic acid dimethyl ester

Downstream raw materials:

7-{4-[4-(2-methoxyphenyl)piperazin-1-yl-butoxy]}-8-chloro-2,3-dihydro-1H-cyclopentene[c]benzopyran-4-one

Refernces

• 1、 Chen, Yin,Lan, Yu,Wang, Songlin,Zhang, Heng,Xu, Xiangqing,Liu, Xin,Yu, Minquan,Liu, Bi-Feng,Zhang, Guisen. "Synthesis and evaluation of new coumarin derivatives as potential atypical antipsychotics". . p. 427 - 439. Retrieved 2014/02/14.