methyl exo-bicyclo<6.1.0>nonane-9-carboxylate | 898838-43-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl exo-bicyclo<6.1.0>nonane-9-carboxylate
• 英文别名: methyl bicyclo<6.1.0>nonane-9-carboxylate；endo-9-Methoxycarbonyl-cis-bicyclo<6.1.0>nonan；exo-9-Methoxycarbonyl-cis-bicyclo<6.1.0>nonan；methyl exo-bicyclo[6.1.0]nonane-9-carboxylate；9-Methoxycarbonyl-cis-bicyclo[6.1.0]nonan；Methyl bicyclo[6.1.0]nonane-9-carboxylate
• CAS: 898838-43-2
• 化学式: C₁₁H₁₈O₂
• mdl: MFCD06804460
• 分子量: 182.263
• InChiKey: FOVIUQDFFNBZFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.909
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  顺-环辛烯 、 重氮乙酸甲酯 在 dirhodium tetraacetate 作用下， 反应 4.0h， 以31%的产率得到methyl exo-bicyclo<6.1.0>nonane-9-carboxylate
  参考文献：
  名称：

  Preparation of diastereomerically pure 9-carboxybicyclo[6.1.0]nonane derivatives

  摘要：

  Reactions of cyclooctene (1) with dibromocyanoacetic esters and copper(I) bromide give (8-10) : 1 mixtures of isomers (2, 3), not stereochemically pure compounds as reported by others. The stereochemistry is elucidated by independent synthesis of one diastereomer (3a). Carbenoid addition of alkoxycarbonylmethylene to 1 and 1,5-cyclooctadiene leads also to exo/endo adduct mixtures. Methods are developed to generate diastereomerically pure compounds (exo-7a, exo-8, endo-9, exo-10, endo-10) from these. Endo esters of this series undergo very facile base catalyzed epimerization.

  DOI：

  10.1002/prac.19963380161

文献信息

• Reductive Carbonylation of<i>gem</i>-Dihalogenocyclopropanes by Pentacarbonyliron(0) in the Presence of Sodium Methoxide
  作者：Françoise Reyne、Bernard Waegell、Pierre Brun

  DOI：10.1246/bcsj.68.1162

  日期：1995.4

  The reaction of gem-dihalogenocyclopropanes derivatives with (tetracarbonyl)(methoxycarbonylato)ferrate(I−) has been investigated; gem-dibromocyclopropanes and gem-chlorobromocyclopropane derivatives are reduced and carbonylated. It could be shown that a bromo ester such as methyl 1-bromo-2-phenylcyclopropanecarboxylate is an intermediate in the transformation of 1,1-dibromo-2-phenylcyclopropane into methyl cis- and trans-2-phenylcyclopropanecarboxylates and dimethyl 2-phenyl-1,1-cyclopropanedicarboxylate.

  研究了偕二卤代环丙烷衍生物与(四羰基)(甲氧基羰基)铁酸盐(I−)的反应；偕二溴环丙烷和偕氯溴环丙烷衍生物被还原和羰基化。可以证明，溴代酯如1-溴-2-苯基环丙烷甲酸甲酯是1,1-二溴-2-苯基环丙烷转化为顺式和反式-2-苯基环丙烷甲酸甲酯和2-苯基环丙烷二甲酯的中间体。 1,1-环丙烷二甲酸酯。
• Transition-metal-catalyzed reactions of diazo compounds. 1. Cyclopropanation of double bonds
  作者：Andre J. Anciaux、Andre J. Hubert、Alfred F. Noels、N. Petiniot、Philippe Teyssie

  DOI：10.1021/jo01292a029

  日期：1980.2
• Synthesis of cyclopropane derivatives from olefins by the reaction with organic gem-dihalides and copper
  作者：Nariyoshi Kawabata、Ichiro Kamemura、Michiharu Naka

  DOI：10.1021/ja00502a034

  日期：1979.4
• Preparation of diastereomerically pure 9-carboxybicyclo[6.1.0]nonane derivatives
  作者：Eckehard Volker Dehmlow、Olaf Pl�ckebaum

  DOI：10.1002/prac.19963380161

  日期：——

  Reactions of cyclooctene (1) with dibromocyanoacetic esters and copper(I) bromide give (8-10) : 1 mixtures of isomers (2, 3), not stereochemically pure compounds as reported by others. The stereochemistry is elucidated by independent synthesis of one diastereomer (3a). Carbenoid addition of alkoxycarbonylmethylene to 1 and 1,5-cyclooctadiene leads also to exo/endo adduct mixtures. Methods are developed to generate diastereomerically pure compounds (exo-7a, exo-8, endo-9, exo-10, endo-10) from these. Endo esters of this series undergo very facile base catalyzed epimerization.