2,3,6,7-tetrahydro-s-indacene-1,5-dione | 81423-50-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2,3,6,7-tetrahydro-s-indacene-1,5-dione
• 英文别名: Tetrahydro-s-indacen-1,5-dion；s-hydrindacene-1,5-dione
• CAS: 81423-50-9
• 化学式: C₁₂H₁₀O₂
• 分子量: 186.21
• InChiKey: HDFLMPNKTHXEMR-UHFFFAOYSA-N

物化性质

• 熔点：
  230-231 °C
• 沸点：
  404.3±45.0 °C(Predicted)
• 密度：
  1.324±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3,6,7-tetrahydro-s-indacene-1,5-dione 在 氢氧化钾 、 正丁基锂 、 溴 、 对甲苯磺酸 作用下， 以 甲醇 、 溶剂黄146 、 苯 为溶剂， 反应 290.83h， 生成 1',4'-dichloro-1',4'-dimethyl-1',1a',3a',4',4a',6a'-hexahydrodispiro[[1,3]dioxolane-2,3'-dicyclopropa[a,g]-s-indacene-6',2''-[1,3]dioxolane]
  参考文献：
  名称：

  Synthesis of two bis-m-quinomethanes. An experimental study of connectivity effects on the equal-parity criterion for low-spin ground states in alternant non-Kekule molecules

  摘要：

  DOI：

  10.1021/ja00266a021
• 作为产物：
  描述：

  对亚苯基二丙酸 在 PPA 作用下， 反应 0.67h， 以6%的产率得到2,3,6,7-tetrahydro-s-indacene-1,5-dione
  参考文献：
  名称：

  Synthesis of two bis-m-quinomethanes. An experimental study of connectivity effects on the equal-parity criterion for low-spin ground states in alternant non-Kekule molecules

  摘要：

  DOI：

  10.1021/ja00266a021

文献信息

• Rhodium complex-catalyzed desilylative cyclocarbonylation of 1-aryl-2-(trimethylsilyl)acetylenes: a new route to 2,3-dihydro-1H-inden-1-ones
  作者：Ryo Takeuchi、Hiroyuki Yasue

  DOI：10.1021/jo00072a020

  日期：1993.9

  Under water gas shift reaction conditions, 1-aryl-2-(trimethylsilyl)acetylenes undergo Rh-catalyzed desilylative cyclocarbonylation to give 2,3-dihydro-1H-inden-1-ones and trimethylsilanol. A wide variety of functional groups, such as methoxy, chloro, acetyl, ethoxycarbonyl, cyano, and trifluoromethyl, are tolerated on the aromatic ring under the reaction conditions. The products were obtained in good to excellent yield whether the substituent on the aromatic ring was electron-donating or electron-withdrawing. The cyclizations of substrates bearing a meta substituent on the aromatic ring regiospecifically gave 5-substituted-2,3-dihydro-1H-inden-1-ones except when the meta substituent was a methoxy group. The desilylative cyclocarbonylation is an alternative to the conventional preparation of 2,3-dihydro-1H-inden-1-ones, an intramolecular Friedel-Crafts acylation. A possible mechanism for the process is described.
• Bickert, Peter; Boekelheide, Virgil; Hafner, Klaus, Angewandte Chemie, 1982, vol. 94, # 4, p. 308
  作者：Bickert, Peter、Boekelheide, Virgil、Hafner, Klaus

  DOI：——

  日期：——
• BICKERT, P.;BOEKELHEIDE, V.;HAFNER, K., ANGEW. CHEM., 1982, 94, N 4, 308
  作者：BICKERT, P.、BOEKELHEIDE, V.、HAFNER, K.

  DOI：——

  日期：——
• Synthesis of two bis-m-quinomethanes. An experimental study of connectivity effects on the equal-parity criterion for low-spin ground states in alternant non-Kekule molecules
  作者：David E. Seeger、Paul M. Lahti、Angelo R. Rossi、Jerome A. Berson

  DOI：10.1021/ja00266a021

  日期：1986.3