3,3,3',3'-tetrabromo-5,5',6,6'-tetramethoxy-2,2'-spirobiindan-1,1'-dione | 1027369-69-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 3,3,3',3'-tetrabromo-5,5',6,6'-tetramethoxy-2,2'-spirobiindan-1,1'-dione
• 英文别名: 3,3,3',3'-Tetrabromo-5,5',6,6'-tetramethoxy-2,2'-spirobi[indene]-1,1'-dione
• CAS: 1027369-69-2
• 化学式: C₂₁H₁₆Br₄O₆
• 分子量: 683.97
• InChiKey: PNTXXMQYICNTEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,3,3',3'-tetrabromo-5,5',6,6'-tetramethoxy-2,2'-spirobiindan-1,1'-dione 在 水 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 4.0h， 生成 5,5',6,6'-tetramethoxy-2,2'-spirobiindan-1,1',3,3'-tetraone
  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：

  3,4-二甲氧基苄氯 在 磷酸酐 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 sodium ethanolate 作用下， 以 四氯化碳 、 乙醇 、 水 、 甲苯 为溶剂， 反应 120.5h， 生成 3,3,3',3'-tetrabromo-5,5',6,6'-tetramethoxy-2,2'-spirobiindan-1,1'-dione
  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.