(S)-1-(2-methyl-5-phenyl-3-thienyl)-2-[2-(3-methyl-1-penten-1-yl)-5-phenyl-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopentene | 249932-09-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: (S)-1-(2-methyl-5-phenyl-3-thienyl)-2-[2-(3-methyl-1-penten-1-yl)-5-phenyl-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopentene
• 英文别名: 3-[3,3,4,4,5,5-hexafluoro-2-[2-[(E,3S)-3-methylpent-1-enyl]-5-phenylthiophen-3-yl]cyclopenten-1-yl]-2-methyl-5-phenylthiophene
• CAS: 249932-09-0
• 化学式: C₃₂H₂₆F₆S₂
• 分子量: 588.681
• InChiKey: OGSSBMOXQNVAJO-VVLLFNJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-1-(2-methyl-5-phenyl-3-thienyl)-2-[2-(3-methyl-1-penten-1-yl)-5-phenyl-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopentene 以 正己烷 为溶剂， 生成 (9aR,9bR)-4,4,5,5,6,6-Hexafluoro-9b-methyl-9a-((E)-(S)-3-methyl-pent-1-enyl)-2,8-diphenyl-5,6,9a,9b-tetrahydro-4H-1,9-dithia-trindene 、 (9aS,9bS)-4,4,5,5,6,6-Hexafluoro-9b-methyl-9a-((E)-(S)-3-methyl-pent-1-enyl)-2,8-diphenyl-5,6,9a,9b-tetrahydro-4H-1,9-dithia-trindene
  参考文献：
  名称：

  Diastereoselection in Crystalline State Photochromism of a Diarylethene Having a Chiral Substituent

  摘要：

  具有手性取代基的二芳香族化合物在结晶相中发生了非对映选择性光环化反应，而在溶液中则没有观察到这种选择性。

  DOI：

  10.1246/cl.1999.1003
• 作为产物：
  描述：

  3,5-dibromo-2-(1,3-dioxolan-2-yl)-thiophene 在 四(三苯基膦)钯 、 正丁基锂 、 4-甲基苯磺酸吡啶 、 sodium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 39.5h， 生成 (S)-1-(2-methyl-5-phenyl-3-thienyl)-2-[2-(3-methyl-1-penten-1-yl)-5-phenyl-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopentene
  参考文献：
  名称：

  Reversible Diastereoselective Photocyclization of a Diarylethene in a Single-Crystalline Phase

  摘要：

  Optically active photochromic (S)- and (R)-1-(2-methyl-5-phenyl-3-thienyl)-2-[2-(3-methyl-1-penten-1-yl)-5-phenyl-3-thienyl]-3,3,3,4,5,5-hexafluorocyclopentanes ((S)-1a and (R)-1a) were synthesized. X-ray crystallographic measurement showed that (S)-1a and (R)-1a single crystals adopted orthorhombic chiral space group P2(1)2(1)2(1) and the open-ring isomers were packed in the crystals in only one conformer of the possible two atropisomers. Upon irradiation with 366 nm light (S)-1a and (R)-1a underwent reversible photocyclization reactions both in solution and in the single-crystalline state, and in the crystalline phase almost only one closed-ring diastereomer was produced, while the diastereoselection was not observed in solution. The dominant diastereomer produced from (S)-1a was determined to be (S,R,R)-1b by X-ray crystallographic analysis.

  DOI：

  10.1021/ja001350o

文献信息

• Reversible Diastereoselective Photocyclization of a Diarylethene in a Single-Crystalline Phase
  作者：Tetsuhiro Kodani、Kenji Matsuda、Taro Yamada、Seiya Kobatake、Masahiro Irie

  DOI：10.1021/ja001350o

  日期：2000.10.1

  Optically active photochromic (S)- and (R)-1-(2-methyl-5-phenyl-3-thienyl)-2-[2-(3-methyl-1-penten-1-yl)-5-phenyl-3-thienyl]-3,3,3,4,5,5-hexafluorocyclopentanes ((S)-1a and (R)-1a) were synthesized. X-ray crystallographic measurement showed that (S)-1a and (R)-1a single crystals adopted orthorhombic chiral space group P2(1)2(1)2(1) and the open-ring isomers were packed in the crystals in only one conformer of the possible two atropisomers. Upon irradiation with 366 nm light (S)-1a and (R)-1a underwent reversible photocyclization reactions both in solution and in the single-crystalline state, and in the crystalline phase almost only one closed-ring diastereomer was produced, while the diastereoselection was not observed in solution. The dominant diastereomer produced from (S)-1a was determined to be (S,R,R)-1b by X-ray crystallographic analysis.
• Diastereoselection in Crystalline State Photochromism of a Diarylethene Having a Chiral Substituent
  作者：Tetsuhiro Kodani、Kenji Matsuda、Taro Yamada、Masahiro Irie

  DOI：10.1246/cl.1999.1003

  日期：1999.9

  A diarylethene having a chiral substituent underwent a diastereoselective photocyclization reaction in the crystalline phase, while the selectivity was not observed in solution.

  具有手性取代基的二芳香族化合物在结晶相中发生了非对映选择性光环化反应，而在溶液中则没有观察到这种选择性。