pentane-2,3,4-trione-3-thiazol-2-ylhydrazone | 61639-63-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: pentane-2,3,4-trione-3-thiazol-2-ylhydrazone
• 英文别名: Pentan-2,3,4-trion-3-thiazol-2-ylhydrazon；3-(1,3-thiazol-2-ylhydrazinylidene)pentane-2,4-dione
• CAS: 61639-63-2
• 化学式: C₈H₉N₃O₂S
• 分子量: 211.244
• InChiKey: XESHOYQJUXVSLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.09
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  71.42
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  pentane-2,3,4-trione-3-thiazol-2-ylhydrazone 、 乙二胺 以 乙醇 为溶剂， 反应 5.0h， 以70%的产率得到4,4'-(ethane-1,2-diylbis(azaneylylidene))bis(3-(2-(thiazol-2-yl)hydrazineylidene)pentan-2-one)
  参考文献：
  名称：

  Krishnankutty; Sayudevi; Ummathur, Muhammed Basheer, Journal of the Indian Chemical Society, 2008, vol. 85, # 1, p. 48 - 52

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酰丙酮 、 alkaline earth salt of/the/ methylsulfuric acid 在 水 作用下， 生成 pentane-2,3,4-trione-3-thiazol-2-ylhydrazone
  参考文献：
  名称：

  Morgan; Morrow, Journal of the Chemical Society, 1915, vol. 107, p. 1294

  摘要：

  DOI：

文献信息

• Thiazolylazopyrazoles as Nonsymmetric Bis‐Heteroaryl Azo Switches: High‐Yield Visible‐Light Photoisomerization and Increased Z‐Isomer Stability by o‐Carbonylation
  作者：Tongtong Dang、Dongfang Dong、Jiabin Zhang、Yixin He、Zhao-Yang Zhang、Tao Li

  DOI：10.1002/anie.202301992

  日期：——

  AbstractFollowing the progress on mono‐heteroaryl azo switches (Het‐N=N‐Ph), a few bis‐heteroaryl azo switches (Het‐N=N‐Het) have been studied recently, whereas the nonsymmetric bis‐heteroaryl ones (Het1‐N=N‐Het2) that can combine the respective merits of each heterocycle, have received little attention. Here we report thiazolylazopyrazoles as nonsymmetric bis‐heteroaryl azo switches that combine the visible‐light switching character of the thiazole ring and the ease of o‐substitution of the pyrazole ring. Thiazolylazopyrazoles can achieve (near‐)quantitative visible‐light isomerization in both directions and long Z‐isomer thermal half‐lives of several days. In contrast to the drastically destabilizing effect of o‐methylation, o‐carbonylation of the pyrazole ring can remarkably stabilize Z isomers by inducing attractive intramolecular interactions (dispersion, C−H⋅⋅⋅N bond, and lone‐pair⋅⋅⋅π interaction). Our work highlights the importance of the rational combination of two heterocycles and suitable structural substitution in developing bis‐heteroaryl azo switches.