5-(5-chloro-2-methylthiophen-3-yl)-5-oxopentanoic acid | 1314044-02-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-(5-chloro-2-methylthiophen-3-yl)-5-oxopentanoic acid
• CAS: 1314044-02-4
• 化学式: C₁₀H₁₁ClO₃S
• 分子量: 246.715
• InChiKey: VZQOJGFKQVRFGF-UHFFFAOYSA-N

物化性质

• 熔点：
  79-80 °C
• 沸点：
  438.1±45.0 °C(Predicted)
• 密度：
  1.349±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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-chloro-2-methylthiophen-3-yl)-5-oxopentanoic acid 在 aluminum (III) chloride 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 20.0h， 生成 1-(5-bromo-2-methylbenzo[b]thiophen-3-yl)-5-(5-chloro-2-methylthiophen-3-yl)pentane-1,5-dione
  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：

  2-氯-5-甲基噻吩 、 戊二酸酐 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 15.5h， 以60%的产率得到5-(5-chloro-2-methylthiophen-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

文献信息

• Synthesis and Characterization of Nonsymmetric Cyclopentene-Based Dithienylethenes
  作者：Vasily A. Migulin、Michael M. Krayushkin、Valery A. Barachevsky、Olga I. Kobeleva、Tatyana M. Valova、Konstantin A. Lyssenko

  DOI：10.1021/jo201966g

  日期：2012.1.6

  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.