1-[2-(1-methoxymethoxyethyl)benzo[b]thiophen-3-yl]-2-(2-methylbenzo[b]thiophen-3-yl)hexafluorocyclopentene | 560108-24-9

• 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-(1-methoxymethoxyethyl)benzo[b]thiophen-3-yl]-2-(2-methylbenzo[b]thiophen-3-yl)hexafluorocyclopentene
• 英文别名: 3-[3,3,4,4,5,5-Hexafluoro-2-[2-[1-(methoxymethoxy)ethyl]-1-benzothiophen-3-yl]cyclopenten-1-yl]-2-methyl-1-benzothiophene；3-[3,3,4,4,5,5-hexafluoro-2-[2-[1-(methoxymethoxy)ethyl]-1-benzothiophen-3-yl]cyclopenten-1-yl]-2-methyl-1-benzothiophene
• CAS: 560108-24-9
• 化学式: C₂₆H₂₀F₆O₂S₂
• 分子量: 542.566
• InChiKey: ZKPZCDMUMVFBCL-UHFFFAOYSA-N

物化性质

• 沸点：
  547.2±50.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  74.9
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-[2-(1-methoxymethoxyethyl)benzo[b]thiophen-3-yl]-2-(2-methylbenzo[b]thiophen-3-yl)hexafluorocyclopentene 以 正己烷 为溶剂， 生成 (1S,2R)-12,12,13,13,14,14-hexafluoro-1-[(1S)-1-(methoxymethoxy)ethyl]-2-methyl-3,23-dithiahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-4,6,8,10,15,17,19,21-octaene 、
  参考文献：
  名称：

  Diastereoselective Photochromism of a Bisbenzothienylethene Governed by Steric as Well as Electronic Interactions

  摘要：

  Introduction of an asymmetric center to C-2 of one of the benzothiophene rings of bisbenzothienylperfluorocyclopentene results in a highly diastereoselective photochromic system. The stereogenic center bears a hydrogen atom, a methyl group, and a methoxymethoxy group. The steric as well as the electronic repulsions gave an 87-88% diastereomer excess in various solvents at room temperature with 80-85% conversion to the colored form. The enantioselective synthesis was also carried out. Upon photoirradiation in hexane, a change in optical rotation at 820 nm, where neither the open form nor the colored form absorbs light, was observed repeatedly.

  DOI：

  10.1021/ja029535d
• 作为产物：
  描述：

  1-苯并噻吩-2-乙醇 在 正丁基锂 、 碘 、 碘酸 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 四氯化碳 、 正己烷 为溶剂， 反应 77.0h， 生成 1-[2-(1-methoxymethoxyethyl)benzo[b]thiophen-3-yl]-2-(2-methylbenzo[b]thiophen-3-yl)hexafluorocyclopentene
  参考文献：
  名称：

  Diastereoselective Photochromism of a Bisbenzothienylethene Governed by Steric as Well as Electronic Interactions

  摘要：

  Introduction of an asymmetric center to C-2 of one of the benzothiophene rings of bisbenzothienylperfluorocyclopentene results in a highly diastereoselective photochromic system. The stereogenic center bears a hydrogen atom, a methyl group, and a methoxymethoxy group. The steric as well as the electronic repulsions gave an 87-88% diastereomer excess in various solvents at room temperature with 80-85% conversion to the colored form. The enantioselective synthesis was also carried out. Upon photoirradiation in hexane, a change in optical rotation at 820 nm, where neither the open form nor the colored form absorbs light, was observed repeatedly.

  DOI：

  10.1021/ja029535d

文献信息

• Diastereoselective Photochromism of a Bisbenzothienylethene Governed by Steric as Well as Electronic Interactions
  作者：Yasushi Yokoyama、Hidenori Shiraishi、Yutaka Tani、Yayoi Yokoyama、Yoshitaka Yamaguchi

  DOI：10.1021/ja029535d

  日期：2003.6.1

  Introduction of an asymmetric center to C-2 of one of the benzothiophene rings of bisbenzothienylperfluorocyclopentene results in a highly diastereoselective photochromic system. The stereogenic center bears a hydrogen atom, a methyl group, and a methoxymethoxy group. The steric as well as the electronic repulsions gave an 87-88% diastereomer excess in various solvents at room temperature with 80-85% conversion to the colored form. The enantioselective synthesis was also carried out. Upon photoirradiation in hexane, a change in optical rotation at 820 nm, where neither the open form nor the colored form absorbs light, was observed repeatedly.