1-{(R)-2-(1-hydroxyethyl)-3-benzo[b]thienyl}-2-{(R)-3-(1-hydroxyethyl)-2-benzo[b]thienyl}-3,3,4,4,5,5-hexafluorocyclopentene | 1263271-96-0

• 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-{(R)-2-(1-hydroxyethyl)-3-benzo[b]thienyl}-2-{(R)-3-(1-hydroxyethyl)-2-benzo[b]thienyl}-3,3,4,4,5,5-hexafluorocyclopentene
• 英文别名: (1R)-1-[2-[3,3,4,4,5,5-hexafluoro-2-[2-[(1R)-1-hydroxyethyl]-1-benzothiophen-3-yl]cyclopenten-1-yl]-1-benzothiophen-3-yl]ethanol
• CAS: 1263271-96-0
• 化学式: C₂₅H₁₈F₆O₂S₂
• 分子量: 528.539
• InChiKey: BGFQRYHDVQNZNU-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  96.9
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  五氟丙酸 、 1-{(R)-2-(1-hydroxyethyl)-3-benzo[b]thienyl}-2-{(R)-3-(1-hydroxyethyl)-2-benzo[b]thienyl}-3,3,4,4,5,5-hexafluorocyclopentene 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以69%的产率得到1-{(R)-2-(1-pentafluoropropanoyloxyethyl)-3-benzo[b]thienyl}-2-{(R)-3-(1-pentafluoropropanoyloxyethyl)-2-benzo[b]thienyl}-3,3,4,4,5,5-hexafluorocyclopentene
  参考文献：
  名称：

  Highly diastereoselective photochromic ring closure of bisbenzothienylethenes possessing dual fluorinated stereocontrollers

  摘要：

  Three regioisomeric bisbenzothienylethenes equipped with two (R)-pentafluoropropanoyloxyethyl groups on both ends of the hexatriene moiety displayed high diastereoselectivity towards light-induced 6 pi-electrocyclization reactions, particularly in polar solvents. In non-polar solvents such as hexane and octafluorotoluene, however, diastereoselectivity was not very high owing to the fluorophobic or less fluorophilic interactions, respectively, between the fluoroalkanoyl side chains and the solvent molecules. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2010.03.008
• 作为产物：
  描述：

  (R,R)-1-[2-(1-methoxymethoxyethyl)-3-benzo[b]thienyl]-2-[3-(1-methoxymethoxyethyl)-2-benzo[b]thienyl]hexafluorocyclopentene 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 以81%的产率得到1-{(R)-2-(1-hydroxyethyl)-3-benzo[b]thienyl}-2-{(R)-3-(1-hydroxyethyl)-2-benzo[b]thienyl}-3,3,4,4,5,5-hexafluorocyclopentene
  参考文献：
  名称：

  Highly diastereoselective photochromic ring closure of bisbenzothienylethenes possessing dual fluorinated stereocontrollers

  摘要：

  Three regioisomeric bisbenzothienylethenes equipped with two (R)-pentafluoropropanoyloxyethyl groups on both ends of the hexatriene moiety displayed high diastereoselectivity towards light-induced 6 pi-electrocyclization reactions, particularly in polar solvents. In non-polar solvents such as hexane and octafluorotoluene, however, diastereoselectivity was not very high owing to the fluorophobic or less fluorophilic interactions, respectively, between the fluoroalkanoyl side chains and the solvent molecules. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2010.03.008

文献信息

• Highly diastereoselective photochromic ring closure of bisbenzothienylethenes possessing dual fluorinated stereocontrollers
  作者：Yasushi Yokoyama、Tomohiko Hasegawa、Takashi Ubukata

  DOI：10.1016/j.dyepig.2010.03.008

  日期：2011.6

  Three regioisomeric bisbenzothienylethenes equipped with two (R)-pentafluoropropanoyloxyethyl groups on both ends of the hexatriene moiety displayed high diastereoselectivity towards light-induced 6 pi-electrocyclization reactions, particularly in polar solvents. In non-polar solvents such as hexane and octafluorotoluene, however, diastereoselectivity was not very high owing to the fluorophobic or less fluorophilic interactions, respectively, between the fluoroalkanoyl side chains and the solvent molecules. (C) 2010 Elsevier Ltd. All rights reserved.