3-Chloro-5-phenylcyclopent-2-en-1-one | 1162000-28-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-Chloro-5-phenylcyclopent-2-en-1-one
• CAS: 1162000-28-3
• 化学式: C₁₁H₉ClO
• 分子量: 192.645
• InChiKey: TZEYAHNWOFERTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-Chloro-5-phenylcyclopent-2-en-1-one 在 10% rhodium on carbon 、 palladium diacetate 、 potassium carbonate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 水 、 甲苯 、 均三甲苯 为溶剂， 反应 18.0h， 生成 9-hydroxy-6-(4-methoxyphenyl)-9-methyl-4-phenyl-11-(propan-2-yl)tricyclo[5.2.2.0^2,6]undeca-4,10-diene-3,8-dione
  参考文献：
  名称：

  Synthesis of Chamaecypanone C Analogues from in Situ-Generated Cyclopentadienones and Their Biological Evaluation

  摘要：

  A rhodium-catalyzed dehydrogenation protocol for the conversion of 3,5-diarylcyclopentenones to the corresponding 2,4-diarylcyclopentadienones has been developed. With this protocol, analogues of the cytotoxic agent chamaecypanone C have been synthesized via Diels-Alder cycloaddition between the cyclopentadienones and in situ-generated o-quinols. Biological evaluation of these analogues revealed a compound with higher activity as a microtubule inhibitor and cytotoxic agent in comparison with the parent structure.

  DOI：

  10.1021/ja3084708
• 作为产物：
  描述：

  I+/--(2-Chloro-2-propen-1-yl)benzeneacetic acid 在 光气 、 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 生成 3-Chloro-5-phenylcyclopent-2-en-1-one
  参考文献：
  名称：

  Synthesis of Chamaecypanone C Analogues from in Situ-Generated Cyclopentadienones and Their Biological Evaluation

  摘要：

  A rhodium-catalyzed dehydrogenation protocol for the conversion of 3,5-diarylcyclopentenones to the corresponding 2,4-diarylcyclopentadienones has been developed. With this protocol, analogues of the cytotoxic agent chamaecypanone C have been synthesized via Diels-Alder cycloaddition between the cyclopentadienones and in situ-generated o-quinols. Biological evaluation of these analogues revealed a compound with higher activity as a microtubule inhibitor and cytotoxic agent in comparison with the parent structure.

  DOI：

  10.1021/ja3084708

文献信息

• A General Method for the Synthesis of 3,5-Diarylcyclopentenones via Friedel−Crafts Acylation of Vinyl Chlorides
  作者：Yingju Xu、Mark McLaughlin、Cheng-yi Chen、Robert A. Reamer、Peter G. Dormer、Ian W. Davies

  DOI：10.1021/jo900696k

  日期：2009.7.17

  A general approach for the synthesis of 3,5-diarylcyclopentenones was developed. Key aspects of this approach are the intramolecular Friedel-Crafts-type cyclization of vinyl chlorides and subsequent Pd-catalyzed cross-coupling reactions. The requisite vinyl chloride-bearing arylacetic acid precursors are readily available by straightforward alkylation of arylacetic acid esters and undergo cyclization to yield 3-chloro-5-aryl-2-cyclopentenones when treated with AlCl(3). The vinylogous acid chloride functionality present in these immediate products allows for further elaboration via Pd-catalyzed cross-coupling chemistry, leading to a diverse array of products.
• Synthesis of Chamaecypanone C Analogues from <i>in Situ</i>-Generated Cyclopentadienones and Their Biological Evaluation
  作者：Suwei Dong、Tian Qin、Ernest Hamel、John A. Beutler、John A. Porco

  DOI：10.1021/ja3084708

  日期：2012.12.5

  A rhodium-catalyzed dehydrogenation protocol for the conversion of 3,5-diarylcyclopentenones to the corresponding 2,4-diarylcyclopentadienones has been developed. With this protocol, analogues of the cytotoxic agent chamaecypanone C have been synthesized via Diels-Alder cycloaddition between the cyclopentadienones and in situ-generated o-quinols. Biological evaluation of these analogues revealed a compound with higher activity as a microtubule inhibitor and cytotoxic agent in comparison with the parent structure.