2,3-bis(5-methyl-2-phenylthiazol-4-yl)-1-methyl-1H-indole | 1338218-92-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2,3-bis(5-methyl-2-phenylthiazol-4-yl)-1-methyl-1H-indole
• 英文别名: 5-Methyl-4-[1-methyl-2-(5-methyl-2-phenyl-1,3-thiazol-4-yl)indol-3-yl]-2-phenyl-1,3-thiazole；5-methyl-4-[1-methyl-2-(5-methyl-2-phenyl-1,3-thiazol-4-yl)indol-3-yl]-2-phenyl-1,3-thiazole
• CAS: 1338218-92-0
• 化学式: C₂₉H₂₃N₃S₂
• 分子量: 477.654
• InChiKey: QHZLKOWYBUPEEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  87.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-bis(5-methyl-2-phenylthiazol-4-yl)-1-methyl-1H-indole 生成
  参考文献：
  名称：

  Synthesis and photochromic properties of a dithiazolylindole

  摘要：

  A novel photochromic 2,3-dithiazolylindole has been synthesized and its photochromic properties was elucidated. This compound showed reversible photochromism both in solution and in a crystal with no spontaneous bleaching under dark conditions. The photocyclization quantum yield of the dithiazolylindole was as high as 83% in hexane, suggesting the photoreactive conformation was stabilized through intramolecular interactions. X-ray crystal structure analysis revealed that the dithiazolylindole adopted the photoreactive conformation with quasi-C-2 symmetry around the hexatriene moiety in the crystalline state. This conformation was assisted by presumed intramolecular CH/N hydrogen bonding between the central N-methylindole and the side-chain thiazolyl units in combination with steric interactions between methyl groups at the reactive center carbons. The suggestion of intramolecular hydrogen bonding in solution was also supported by a H-1 NMR variable temperature study. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2011.05.027
• 作为产物：
  描述：

  5-methyl-2-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 、 3-bromo-2-iodo-1-methyl-1H-indole 在 palladium diacetate 、 potassium carbonate 、 三(邻甲基苯基)磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以3%的产率得到2,3-bis(5-methyl-2-phenylthiazol-4-yl)-1-methyl-1H-indole
  参考文献：
  名称：

  Synthesis and photochromic properties of a dithiazolylindole

  摘要：

  A novel photochromic 2,3-dithiazolylindole has been synthesized and its photochromic properties was elucidated. This compound showed reversible photochromism both in solution and in a crystal with no spontaneous bleaching under dark conditions. The photocyclization quantum yield of the dithiazolylindole was as high as 83% in hexane, suggesting the photoreactive conformation was stabilized through intramolecular interactions. X-ray crystal structure analysis revealed that the dithiazolylindole adopted the photoreactive conformation with quasi-C-2 symmetry around the hexatriene moiety in the crystalline state. This conformation was assisted by presumed intramolecular CH/N hydrogen bonding between the central N-methylindole and the side-chain thiazolyl units in combination with steric interactions between methyl groups at the reactive center carbons. The suggestion of intramolecular hydrogen bonding in solution was also supported by a H-1 NMR variable temperature study. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2011.05.027