2-(4-Bromophenyl)-4-chloropent-4-enoic acid | 1162000-14-7

• 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: 2-(4-Bromophenyl)-4-chloropent-4-enoic acid
• CAS: 1162000-14-7
• 化学式: C₁₁H₁₀BrClO₂
• 分子量: 289.556
• InChiKey: KBMLWKDGOORXHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-Bromophenyl)-4-chloropent-4-enoic acid 在 草酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  A General Method for the Synthesis of 3,5-Diarylcyclopentenones via Friedel−Crafts Acylation of Vinyl Chlorides

  摘要：

  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.

  DOI：

  10.1021/jo900696k
• 作为产物：
  描述：

  在 sodium hydroxide 、 水 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 甲基叔丁基醚 、 水 为溶剂， 反应 0.33h， 生成 2-(4-Bromophenyl)-4-chloropent-4-enoic acid
  参考文献：
  名称：

  A General Method for the Synthesis of 3,5-Diarylcyclopentenones via Friedel−Crafts Acylation of Vinyl Chlorides

  摘要：

  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.

  DOI：

  10.1021/jo900696k

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.