1,1-dibromodispiro[2.0.5.1]decane

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: 1,1-dibromodispiro[2.0.5.1]decane
• 英文别名: 2,2-Dibromodispiro[2.0.54.13]decane；2,2-dibromodispiro[2.0.54.13]decane
• 化学式: C₁₀H₁₄Br₂
• 分子量: 294.029
• InChiKey: PWZBDPFEZSOLFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,1-dibromodispiro[2.0.5.1]decane 在 甲基锂 作用下， 以 乙醚 为溶剂， 以75%的产率得到1,1'-ethane-1,2-diylbis(2-bromospiro[3.5]non-1-ene)
  参考文献：
  名称：

  Carbenoid rearrangement in the series of substituted gem-dibromospiropentanes

  摘要：

  A series of new substituted gem-dibromospiropentanes was studied in a reaction with methyllithium at -55...-50 degrees C. This reaction is a carbenoid rearrangement that leads to the formation of monomeric and dimeric bromocyclobutenes and also to the products of cyclobutylidene insertion into a C-H bond of the solvent depending on the character of substituents in the dibromospiropentane fragment.

  DOI：

  10.1134/s1070428008070038
• 作为产物：
  描述：

  三溴甲烷 、 1-methylenespiro[2.5]octane 在 potassium tert-butylate 作用下， 以 Petroleum ether 为溶剂， 以52%的产率得到1,1-dibromodispiro[2.0.5.1]decane
  参考文献：
  名称：

  Carbenoid rearrangement of gem-dihalogenospiropentanes

  摘要：

  A skeletal rearrangement of dihalogenospiropentanes in the presence of alkyllithium reagents has been systematically studied using a number of gem-dibromospiropentanes. The scope and limitations of this carbenoid rearrangement are outlined and its mechanism is discussed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.086

文献信息

• Carbenoid rearrangement of gem-dihalogenospiropentanes
  作者：Elena B. Averina、Rashad R. Karimov、Kseniya N. Sedenkova、Yurii K. Grishin、Tamara S. Kuznetzova、Nikolai S. Zefirov

  DOI：10.1016/j.tet.2006.06.086

  日期：2006.9

  A skeletal rearrangement of dihalogenospiropentanes in the presence of alkyllithium reagents has been systematically studied using a number of gem-dibromospiropentanes. The scope and limitations of this carbenoid rearrangement are outlined and its mechanism is discussed. (c) 2006 Elsevier Ltd. All rights reserved.
• Carbenoid rearrangement in the series of substituted gem-dibromospiropentanes
  作者：K. N. Sedenkova、E. B. Averina、Yu. K. Grishin、T. S. Kuznetsova、N. S. Zefirov

  DOI：10.1134/s1070428008070038

  日期：2008.7

  A series of new substituted gem-dibromospiropentanes was studied in a reaction with methyllithium at -55...-50 degrees C. This reaction is a carbenoid rearrangement that leads to the formation of monomeric and dimeric bromocyclobutenes and also to the products of cyclobutylidene insertion into a C-H bond of the solvent depending on the character of substituents in the dibromospiropentane fragment.