1,2-bis<6-(4-chlorobutyl)-2-methylbenzothiophen-3-yl>hexafluorocyclopentene | 159617-36-4

• 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: 1,2-bis<6-(4-chlorobutyl)-2-methylbenzothiophen-3-yl>hexafluorocyclopentene
• 英文别名: 6-(4-Chlorobutyl)-3-[2-[6-(4-chlorobutyl)-2-methyl-1-benzothiophen-3-yl]-3,3,4,4,5,5-hexafluorocyclopenten-1-yl]-2-methyl-1-benzothiophene；6-(4-chlorobutyl)-3-[2-[6-(4-chlorobutyl)-2-methyl-1-benzothiophen-3-yl]-3,3,4,4,5,5-hexafluorocyclopenten-1-yl]-2-methyl-1-benzothiophene
• CAS: 159617-36-4
• 化学式: C₃₁H₂₈Cl₂F₆S₂
• 分子量: 649.592
• InChiKey: DVMWZYVGHMIICS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.69
• 重原子数：
  41.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1,2-bis<6-(4-chlorobutyl)-2-methylbenzothiophen-3-yl>hexafluorocyclopentene 在 sodium iodide 作用下， 以 丁酮 为溶剂， 反应 24.0h， 以100%的产率得到1,2-bis<6-(4-iodobutyl)-2-methylbenzothiophen-3-yl>hexafluorocyclopentene
  参考文献：
  名称：

  Photochromic Diarylethenes with Intralocking Arms

  摘要：

  1,2-Bis(2-methylbenzo[b]thiophen-3-yl)perfluorocyclopentenes with carboxyalkyl or alkyl mercaptan groups at 6 and 6' positions of the benzothiophene rings were synthesized with the aim of controlling the photochromic reactivity by external stimulation, such as chemicals or heat treatment. 1,2-Diarylethenes with heterocyclic five-membered rings have two atropisomers, and the photochromic reactivity depends on the conformation. When the molecule was fixed in a parallel conformation with intramolecular hydrogen bonds or an intramolecular disulfide linkage, the photochromic reactivity was completely inhibited. The molecule again became photoactive when the intramolecular lock was unclasped by the addition of hydrogen bond breaking or reducing agents. The diarylethene with carboxyethyl groups showed a thermal reaction threshold in decalin. At temperatures below 50 degrees C the molecule was photochemically inactive, while the photochromic property was recovered upon heating above 100 degrees C, at which temperatures the intramolecular hydrogen bonds are broken.

  DOI：

  10.1021/ja00101a010
• 作为产物：
  描述：

  1,2-bis<6-(4-chloro-1-oxobutyl)-2-methylbenzothiophen-3-yl>hexafluorocyclopentene 在 三氯化铝 、 硼烷-叔丁基胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以72%的产率得到1,2-bis<6-(4-chlorobutyl)-2-methylbenzothiophen-3-yl>hexafluorocyclopentene
  参考文献：
  名称：

  Photochromic Diarylethenes with Intralocking Arms

  摘要：

  1,2-Bis(2-methylbenzo[b]thiophen-3-yl)perfluorocyclopentenes with carboxyalkyl or alkyl mercaptan groups at 6 and 6' positions of the benzothiophene rings were synthesized with the aim of controlling the photochromic reactivity by external stimulation, such as chemicals or heat treatment. 1,2-Diarylethenes with heterocyclic five-membered rings have two atropisomers, and the photochromic reactivity depends on the conformation. When the molecule was fixed in a parallel conformation with intramolecular hydrogen bonds or an intramolecular disulfide linkage, the photochromic reactivity was completely inhibited. The molecule again became photoactive when the intramolecular lock was unclasped by the addition of hydrogen bond breaking or reducing agents. The diarylethene with carboxyethyl groups showed a thermal reaction threshold in decalin. At temperatures below 50 degrees C the molecule was photochemically inactive, while the photochromic property was recovered upon heating above 100 degrees C, at which temperatures the intramolecular hydrogen bonds are broken.

  DOI：

  10.1021/ja00101a010