1-(2-methyl-5-phenyl-3-thienyl)-2-[2-(3-methyl-1-hydroxy-1-pentyl)-5-phenyl-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopentene | 308255-25-6

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 1-(2-methyl-5-phenyl-3-thienyl)-2-[2-(3-methyl-1-hydroxy-1-pentyl)-5-phenyl-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopentene
• 英文别名: (3S)-1-[3-[3,3,4,4,5,5-hexafluoro-2-(2-methyl-5-phenylthiophen-3-yl)cyclopenten-1-yl]-5-phenylthiophen-2-yl]-3-methylpentan-1-ol
• CAS: 308255-25-6
• 化学式: C₃₂H₂₈F₆OS₂
• 分子量: 606.696
• InChiKey: YZMOPNFUZZGOFC-VEXWJQHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  41
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-(2-methyl-5-phenyl-3-thienyl)-2-[2-(3-methyl-1-hydroxy-1-pentyl)-5-phenyl-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopentene 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 以39%的产率得到(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
• 作为产物：
  描述：

  1-(2-methyl-5-phenyl-3-thienyl)-2-[2-(2,5-dioxolanyl)-5-phenyl-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopentene 在 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 13.0h， 生成 1-(2-methyl-5-phenyl-3-thienyl)-2-[2-(3-methyl-1-hydroxy-1-pentyl)-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