trans-anti-3,3'-(2-thienyl)-3,3'-dihydroxyl-[2,2'-bi-1H-indene]-1,1'-dione | 1096359-47-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: trans-anti-3,3'-(2-thienyl)-3,3'-dihydroxyl-[2,2'-bi-1H-indene]-1,1'-dione
• CAS: 1096359-47-5
• 化学式: C₂₆H₁₆O₄S₂
• 分子量: 456.543
• InChiKey: MMPCEXMQGSXZDI-YWRGTUKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.67
• 重原子数：
  32.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  74.6
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  2-溴噻吩 、 [2,2′-bi-1H-indene]-3,3′-dihydroxy-1,1′-dione 在 magnesium 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 28.66h， 以30.1%的产率得到trans-anti-3,3'-(2-thienyl)-3,3'-dihydroxyl-[2,2'-bi-1H-indene]-1,1'-dione
  参考文献：
  名称：

  Synthesis and properties of photochromic biindenylidenedione derivatives containing thiophene groups, and new insights into the reaction of 2,2′-biindanylidene-1,1′,3,3′-tetraone with Grignard reagent

  摘要：

  Three indenone derivatives (1: 2-[3'-hydroxy-3'-(2-thienyl)indanone-2'-yl]-3-(2-thienyl)indenone; 2: trans-anti-3,3'-(2-thienyl)-3,3'-dihydroxy-[2,2'-bi-1H-indene]-1,1'dione and 3: trans-syn-3,3'-(2-thienyl)-3,3'-dihydroxy-[2,2'-bi-1H-indene]-1,1'-dione) were obtained in a one-pot reaction of 2,2'-biindanylidene-1,1',3,3'-tetraone with 2-thienylmagnesium bromide. Their structures were characterized by means of IR, H-1 NMR, MS, elemental analysis, and X-ray crystallography. The photochromic and photoinduced radical behaviors of these compounds were investigated by means of solid UV-vis spectroscopy and electron spin resonance (ESR) spectroscopy. The results show that compounds 2 and 3 exhibit photochromism in the solid state, whereas compound I does not. The relationship between the crystal structures and photochemical properties is also discussed. Based on the formation and product distribution of compounds 1, 2, and 3, a plausible pathway is suggested for the reaction of 2,2'-biindanylidene-1,1',3,3'-tetraone with 2-thienylmagnesium bromide. The findings obtained in this study also provide new insights into the addition-oxidation mechanism for the reaction of 2,2'-biindanylidene-1,1',3,3'-tetraone with Grignard reagent. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2008.03.029