1-(2-methyl-5-azidomethyl-3-thienyl)-2-[2-methyl-5-(4-azidomethyl)phenyl-3-thienyl]perfluorocyclopentene | 1536084-97-5

• 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-azidomethyl-3-thienyl)-2-[2-methyl-5-(4-azidomethyl)phenyl-3-thienyl]perfluorocyclopentene
• 英文别名: 3-[2-[5-(Azidomethyl)-2-methylthiophen-3-yl]-3,3,4,4,5,5-hexafluorocyclopenten-1-yl]-5-[4-(azidomethyl)phenyl]-2-methylthiophene；3-[2-[5-(azidomethyl)-2-methylthiophen-3-yl]-3,3,4,4,5,5-hexafluorocyclopenten-1-yl]-5-[4-(azidomethyl)phenyl]-2-methylthiophene
• CAS: 1536084-97-5
• 化学式: C₂₃H₁₆F₆N₆S₂
• 分子量: 554.543
• InChiKey: WEIZMJVINVKWNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  85.2
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1-(2-methyl-5-azidomethyl-3-thienyl)-2-[2-methyl-5-(4-azidomethyl)phenyl-3-thienyl]perfluorocyclopentene 、 2-炔丙基-四-O-乙酰基-β-D-吡喃葡萄糖苷 在 copper(II) sulfate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 以68%的产率得到[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[1-[[4-[4-[3,3,4,4,5,5-hexafluoro-2-[2-methyl-5-[[4-[[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxymethyl]triazol-1-yl]methyl]thiophen-3-yl]cyclopenten-1-yl]-5-methylthiophen-2-yl]phenyl]methyl]triazol-4-yl]methoxy]oxan-2-yl]methyl acetate
  参考文献：
  名称：

  The effects of phenyl-bridged glucosyltriazolyl groups on the properties of water-soluble diarylethene derivatives

  摘要：

  Three water-soluble diarylethenes with glycosyltriazolyl groups and variable phenyl units have been synthesized, and their properties, such as water solubility, photochromism, and fluorescence have been discussed. Upon alternating irradiation with UV and visible light, each of the diarylethenes exhibited favorable photochromism and functioned as fluorescent switches in water. Experimental results showed that their water solubility as well as absorption features, cyclization quantum yields, photoconversion ratios, thermal stability, and fatigue resistance exhibited a strong correlation with the number of phenyl-bridged glucosyltriazolyl groups in diarylethene systems. The absorption maximum, thermal stability, and fatigue resistance were significantly improved, but the water solubility and fluorescent modulation efficiency were suppressed with the increase of the number of phenyl-bridged glucosyltriazolyl groups for these diarylethene derivatives. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.037
• 作为产物：
  描述：

  1-(2-methyl-5-hydroxymethyl-3-thienyl)-2-[2-methyl-5-(4-hydroxymethyl)phenyl-3-thienyl]perfluorocyclopentene 在 叠氮磷酸二苯酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 以91%的产率得到1-(2-methyl-5-azidomethyl-3-thienyl)-2-[2-methyl-5-(4-azidomethyl)phenyl-3-thienyl]perfluorocyclopentene
  参考文献：
  名称：

  The effects of phenyl-bridged glucosyltriazolyl groups on the properties of water-soluble diarylethene derivatives

  摘要：

  Three water-soluble diarylethenes with glycosyltriazolyl groups and variable phenyl units have been synthesized, and their properties, such as water solubility, photochromism, and fluorescence have been discussed. Upon alternating irradiation with UV and visible light, each of the diarylethenes exhibited favorable photochromism and functioned as fluorescent switches in water. Experimental results showed that their water solubility as well as absorption features, cyclization quantum yields, photoconversion ratios, thermal stability, and fatigue resistance exhibited a strong correlation with the number of phenyl-bridged glucosyltriazolyl groups in diarylethene systems. The absorption maximum, thermal stability, and fatigue resistance were significantly improved, but the water solubility and fluorescent modulation efficiency were suppressed with the increase of the number of phenyl-bridged glucosyltriazolyl groups for these diarylethene derivatives. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.037

文献信息

• The effects of phenyl-bridged glucosyltriazolyl groups on the properties of water-soluble diarylethene derivatives
  作者：Shouzhi Pu、Hongliang Liu、Gang Liu、Bing Chen、Zhipeng Tong

  DOI：10.1016/j.tet.2013.12.037

  日期：2014.1

  Three water-soluble diarylethenes with glycosyltriazolyl groups and variable phenyl units have been synthesized, and their properties, such as water solubility, photochromism, and fluorescence have been discussed. Upon alternating irradiation with UV and visible light, each of the diarylethenes exhibited favorable photochromism and functioned as fluorescent switches in water. Experimental results showed that their water solubility as well as absorption features, cyclization quantum yields, photoconversion ratios, thermal stability, and fatigue resistance exhibited a strong correlation with the number of phenyl-bridged glucosyltriazolyl groups in diarylethene systems. The absorption maximum, thermal stability, and fatigue resistance were significantly improved, but the water solubility and fluorescent modulation efficiency were suppressed with the increase of the number of phenyl-bridged glucosyltriazolyl groups for these diarylethene derivatives. (C) 2013 Elsevier Ltd. All rights reserved.