5-(5-bromo-2-methylbenzo[b]thiophen-3-yl)-5-oxopentanoic acid | 1351277-24-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 5-(5-bromo-2-methylbenzo[b]thiophen-3-yl)-5-oxopentanoic acid
• 英文别名: 5-(5-Bromo-2-methyl-1-benzothiophen-3-yl)-5-oxopentanoic acid
• CAS: 1351277-24-1
• 化学式: C₁₄H₁₃BrO₃S
• 分子量: 341.225
• InChiKey: HMKYITRCXGOYQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  82.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(5-bromo-2-methylbenzo[b]thiophen-3-yl)-5-oxopentanoic acid 在 吡啶 、 aluminum (III) chloride 、 tris-(dibenzylideneacetone)dipalladium(0) 、 草酰氯 、 四氯化钛 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 N,N-二甲基甲酰胺 、 sodium t-butanolate 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 49.0h， 生成 4-(tert-butyldimethylsilanyloxymethyl)-1-(3-(2-(5-chloro-2-methylthiophen-3-yl)cyclopent-1-enyl)-2-methylbenzo[b]thiophen-5-yl)piperidine
  参考文献：
  名称：

  Synthesis and Characterization of Nonsymmetric Cyclopentene-Based Dithienylethenes

  摘要：

  Nonsymmetric cyclopentene-based dithienylethenes, containing both thienyl and benzothienyl units, have been synthesized for the first time, employing intramolecular McMurry reaction as a key transformation to target compounds 10 and 16. Photochromic properties of these compounds were examined in toluene and acetonitrile solutions, PMMA layers, solid films, and crystal phase. To explain an unprecedented single-crystalline photochromism phenomena of 10, X-ray crystallographic analysis was performed, revealing a significant influence of strong S center dot center dot center dot S interatomic interactions on the intramolecular distance between two photochemical reaction centers in the molecule. Compound 16 could be further synthetically modified in a step-by-step manner, thus serving as potential key intermediate to various complex bifunctional photochromic molecules.

  DOI：

  10.1021/jo201966g
• 作为产物：
  描述：

  戊二酸酐 、 5-bromo-2-methylbenzothiophene 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以76%的产率得到5-(5-bromo-2-methylbenzo[b]thiophen-3-yl)-5-oxopentanoic acid
  参考文献：
  名称：

  Synthesis and Characterization of Nonsymmetric Cyclopentene-Based Dithienylethenes

  摘要：

  Nonsymmetric cyclopentene-based dithienylethenes, containing both thienyl and benzothienyl units, have been synthesized for the first time, employing intramolecular McMurry reaction as a key transformation to target compounds 10 and 16. Photochromic properties of these compounds were examined in toluene and acetonitrile solutions, PMMA layers, solid films, and crystal phase. To explain an unprecedented single-crystalline photochromism phenomena of 10, X-ray crystallographic analysis was performed, revealing a significant influence of strong S center dot center dot center dot S interatomic interactions on the intramolecular distance between two photochemical reaction centers in the molecule. Compound 16 could be further synthetically modified in a step-by-step manner, thus serving as potential key intermediate to various complex bifunctional photochromic molecules.

  DOI：

  10.1021/jo201966g