2-[1-(甲氧基甲氧基)乙基]-1-苯并噻吩 | 560108-12-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 中文名称: 2-[1-(甲氧基甲氧基)乙基]-1-苯并噻吩
• 英文名称: 2-(1-methoxymethoxyethyl)benzo[b]thiophene
• 英文别名: 2-[1-(Methoxymethoxy)ethyl]-1-benzothiophene；2-[1-(methoxymethoxy)ethyl]-1-benzothiophene
• CAS: 560108-12-5
• 化学式: C₁₂H₁₄O₂S
• 分子量: 222.308
• InChiKey: NVLOTBJCVZMOJN-UHFFFAOYSA-N

物化性质

• 沸点：
  300.4±22.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[1-(甲氧基甲氧基)乙基]-1-苯并噻吩 在 正丁基锂 、 碘 、 碘酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 四氯化碳 、 正己烷 为溶剂， 反应 4.25h， 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
• 作为产物：
  描述：

  苯并噻吩 在 正丁基锂 、 四甲基乙二胺 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 78.5h， 生成 2-[1-(甲氧基甲氧基)乙基]-1-苯并噻吩
  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

• Chiral Helicenoid Diarylethene with Large Change in Specific Optical Rotation by Photochromism¹^,²
  作者：Tomoyuki Okuyama、Yutaka Tani、Kentaro Miyake、Yasushi Yokoyama

  DOI：10.1021/jo0620213

  日期：2007.3.1

  A diarylethene possessing one [4]thiaheterohelicene and one benzothiophene, the latter with a chiral methoxymethoxyethyl group on its C-3 position, was proved to work as a switch of specific optical rotation at a wavelength at which both colored and colorless forms have no absorption in solution. The difference of the specific optical rotation was 1300 degrees between the open form and the photostationary state. The specific optical rotation of one of the isolated optically active major colored forms was -4680 degrees. The conversion to the colored form was 64%, and the diastereomeric excess of photocyclization was 47%.
• 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.