3,3-dibromo-2,2′-spirobiindane-1,1′,3′-trione | 252190-39-9

• 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-dibromo-2,2′-spirobiindane-1,1′,3′-trione
• 英文别名: 3',3'-dibromo-2,2'-spirobiindan-1,3,1'-trione；3',3'-Dibromo-2,2'-spirobi[indene]-1,1',3-trione
• CAS: 252190-39-9
• 化学式: C₁₇H₈Br₂O₃
• 分子量: 420.057
• InChiKey: ZCKYLJCLGDUQKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 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：

  3,3-dibromo-2,2′-spirobiindane-1,1′,3′-trione 在 水 作用下， 以 乙醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 6.0h， 生成 2-[(1,3-Dioxo-indan-2-ylidene)-hydroxy-methyl]-benzoic acid ethyl ester
  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：

  2,2'-spirobiindan-1,1'-dione 在 chromium(VI) oxide 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 溴 作用下， 以 四氯化碳 、 水 、 溶剂黄146 为溶剂， 反应 92.0h， 生成 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

文献信息

• Syntheses, Structures and Optoelectronic Properties of Spiroconjugated Cyclic Ketones
  作者：Jennifer Wilbuer、Gregor Schnakenburg、Birgit Esser

  DOI：10.1002/ejoc.201600235

  日期：2016.5

  development of a short procedure for the synthesis of spiroconjugated tetraketone 1 in two steps with 10 % overall yield and the first-time synthesis of spirocyclic trindone 2. The optoelectronic properties of these compounds based on spectroscopic and electrochemical measurements in combination with DFT calculations as well as their molecular structures in the solid state are presented and discussed

  介绍了对螺共轭酮及其衍生物的合成研究。这些研究导致开发了一种短程序，分两步合成螺共轭四酮 1，总产率为 10%，并首次合成螺环三酮 2。这些化合物的光电特性基于光谱和电化学测量的组合介绍和讨论了 DFT 计算以及它们在固态下的分子结构。
• 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.