1-methylenespiro[2.5]octane | 4372-98-9

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 1-methylenespiro[2.5]octane
• 英文别名: 2-Methylidenespiro[2.5]octane
• CAS: 4372-98-9
• 化学式: C₉H₁₄
• 分子量: 122.21
• InChiKey: YOJPDEVWHBLMQH-UHFFFAOYSA-N

物化性质

• 沸点：
  54.55 °C(Press: 38 Torr)
• 密度：
  0.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 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-methylenespiro[2.5]octane 生成 环亚丙基环己烷
  参考文献：
  名称：

  Thermal reorganizations of C6H8 hydrocarbons

  摘要：

  DOI：

  10.1021/ja00745a020
• 作为产物：
  描述：

  环己乙炔 在 甲醇 、 sodium 作用下， 生成 1-methylenespiro[2.5]octane
  参考文献：
  名称：

  Bezaguet,A.; Bertrand,M., Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1965, vol. 261, p. 1695 - 1698

  摘要：

  DOI：

文献信息

• Bu₂SnIH-Promoted Proximal Bond Cleavage of Methylenecyclopropanes and Successive Radical Cyclization and/or Pd-Catalyzed Coupling Reaction
  作者：Naoki Hayashi、Yusuke Hirokawa、Ikuya Shibata、Makoto Yasuda、Akio Baba

  DOI：10.1021/ja7103729

  日期：2008.3.1

  The unprecedented regioselective hydrostannation of methylenecyclopropanes to give vinyltins was achieved using dibutyliodotin hydride (Bu2SnIH), which could be applied to intramolecular radical cyclization.
• 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.
• gem-Bromochlorospiropentane reactivity toward methyllithium: an unusual carbenoid rearrangement
  作者：Kseniya N. Sedenkova、Elena B. Averina、Yuri K. Grishin、Tamara S. Kuznetzova、Nikolai S. Zefirov

  DOI：10.1016/j.tet.2010.07.054

  日期：2010.10

  A skeletal carbenoid rearrangement of the gem-bromochlorospiropentanes in the presence of methyllithium has been studied. The synthetic and mechanistic aspects of this rearrangement as well as the influence of the halogen atom nature on the reaction pathway are discussed. (C) 2010 Elsevier Ltd. All rights reserved.
• Surface nature of Grignard reagent formation. Chiral 1-methylspiro[2.5]octylmagnesium bromide
  作者：C. Hamdouchi、M. Topolski、V. Goedken、H. M. Walborsky

  DOI：10.1021/jo00063a040

  日期：1993.5

  The synthesis of chiral 1-bromo-1-methylspiro[2.5]octane (13) is described. The absolute configuration of 13 has been established as(S)-(+). From stereochemistry, product analysis, and radical trapping experiments it is concluded that the reaction of chiral 13 with magnesium to form the corresponding Grignard reagent occurs mainly on the surface of the magnesium.