1-(2-methyl-5-phenyl-3-thienyl)-2-[2-(2,5-dioxolanyl)-5-phenyl-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopentene | 308255-24-5

• 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: 1-(2-methyl-5-phenyl-3-thienyl)-2-[2-(2,5-dioxolanyl)-5-phenyl-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopentene
• 英文别名: 3-(2-(2-methyl-5-phenylthiophen-3-yl)perfluorocyclopent-1-en-1-yl-5-phenylthiophen-2-yl)-1,3-dioxolane；2-[3-[3,3,4,4,5,5-Hexafluoro-2-(2-methyl-5-phenylthiophen-3-yl)cyclopenten-1-yl]-5-phenylthiophen-2-yl]-1,3-dioxolane；2-[3-[3,3,4,4,5,5-hexafluoro-2-(2-methyl-5-phenylthiophen-3-yl)cyclopenten-1-yl]-5-phenylthiophen-2-yl]-1,3-dioxolane
• CAS: 308255-24-5
• 化学式: C₂₉H₂₀F₆O₂S₂
• 分子量: 578.599
• InChiKey: OSBDMCUXEVOWMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  39
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 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-methyl-5-phenyl-3-thienyl)-2-[2-(2,5-dioxolanyl)-5-phenyl-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopentene 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 以95%的产率得到1-(2-methyl-5-phenyl-3-thienyl)-2-(2-formyl-5-phenyl-3-thienyl)-3,3,4,4,5,5-hexafluorocyclopentene
  参考文献：
  名称：

  用于胺检测的光敏探头

  摘要：

  我们的新型，简单且准确的比色法基于二芳烃（DAE），可快速检测多种伯胺和仲胺。探针由醛或酮取代的二芳烃组成，它们经过胺诱导的脱色反应，选择性地产生闭环异构体。因此，可以通过光照射在期望的时刻激活这些探针，其灵敏度使得可以检测溶液中浓度低至10 -6  m的胺。另外，将DAE实际固定在纸上可以在30秒内检测出高于12 ppbv阈值的气相中的生物胺，例如尸胺。

  DOI：

  10.1002/anie.201609989
• 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 、 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 13.5h， 生成 1-(2-methyl-5-phenyl-3-thienyl)-2-[2-(2,5-dioxolanyl)-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.
• Light-Activated Sensitive Probes for Amine Detection
  作者：Virginia Valderrey、Aurelio Bonasera、Sebastian Fredrich、Stefan Hecht

  DOI：10.1002/anie.201609989

  日期：2017.2.6

  detection of a wide range of primary and secondary amines. The probes consist of aldehyde‐ or ketone‐substituted diarylethenes, which undergo an amine‐induced decoloration reaction, selectively to give the ring‐closed isomer. Thus, these probes can be activated at the desired moment by light irradiation, with a sensitivity that allows the detection of amines at concentrations as low as 10−6 m in solution

  我们的新型，简单且准确的比色法基于二芳烃（DAE），可快速检测多种伯胺和仲胺。探针由醛或酮取代的二芳烃组成，它们经过胺诱导的脱色反应，选择性地产生闭环异构体。因此，可以通过光照射在期望的时刻激活这些探针，其灵敏度使得可以检测溶液中浓度低至10 -6  m的胺。另外，将DAE实际固定在纸上可以在30秒内检测出高于12 ppbv阈值的气相中的生物胺，例如尸胺。