2,2'-spirobiindan-1,3,1'-trione | 127972-65-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2,2'-spirobiindan-1,3,1'-trione
• 英文别名: spiro[3H-indene-2,2'-indene]-1,1',3'-trione
• CAS: 127972-65-0
• 化学式: C₁₇H₁₀O₃
• 分子量: 262.265
• InChiKey: RPCGOMYEQLXKGR-UHFFFAOYSA-N

物化性质

• 熔点：
  164-165 °C
• 沸点：
  497.5±45.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  51.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2'-spirobiindan-1,3,1'-trione 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 溴 作用下， 以 四氯化碳 为溶剂， 反应 90.0h， 以58%的产率得到3,3-dibromo-2,2′-spirobiindane-1,1′,3′-trione
  参考文献：
  名称：

  Synthesis, Structure, and Nucleophile-Induced Rearrangements of Spiroketones

  摘要：

  Three tetraketones based on the 2,2'-spirobiindan-1,1',3,3'-tetraone skeleton were prepared and investigated. All three compounds show spiroconjugation between their perpendicular pi-networks. The interaction results in lowering of the energy of the LUMO of the systems by ca. 0.2-0.3 eV as compared to non-spiroconjugated models. The spiroketones are susceptible to nucleophile-induced retro-Claisen condensations that lead to molecular rearrangements destroying spiro connectivity.

  DOI：

  10.1021/jo990867j
• 作为产物：
  描述：

  1,3-二苯基丙烷-2,2-二羧酸 在 chromium(VI) oxide 、 三氯化铝 、 五氯化磷 、 三氯化铁 作用下， 以 氯仿 、 水 、 溶剂黄146 为溶剂， 25.0~225.0 ℃ 、666.61 Pa 条件下， 反应 2.92h， 生成 2,2'-spirobiindan-1,3,1'-trione
  参考文献：
  名称：

  Synthesis, Structure, and Nucleophile-Induced Rearrangements of Spiroketones

  摘要：

  Three tetraketones based on the 2,2'-spirobiindan-1,1',3,3'-tetraone skeleton were prepared and investigated. All three compounds show spiroconjugation between their perpendicular pi-networks. The interaction results in lowering of the energy of the LUMO of the systems by ca. 0.2-0.3 eV as compared to non-spiroconjugated models. The spiroketones are susceptible to nucleophile-induced retro-Claisen condensations that lead to molecular rearrangements destroying spiro connectivity.

  DOI：

  10.1021/jo990867j

文献信息

• Synthesis, Structure, and Nucleophile-Induced Rearrangements of Spiroketones
  作者：Przemyslaw Maslak、Sridhar Varadarajan、Jeffrey D. Burkey

  DOI：10.1021/jo990867j

  日期：1999.10.1

  Three tetraketones based on the 2,2'-spirobiindan-1,1',3,3'-tetraone skeleton were prepared and investigated. All three compounds show spiroconjugation between their perpendicular pi-networks. The interaction results in lowering of the energy of the LUMO of the systems by ca. 0.2-0.3 eV as compared to non-spiroconjugated models. The spiroketones are susceptible to nucleophile-induced retro-Claisen condensations that lead to molecular rearrangements destroying spiro connectivity.