1,2-bis(methylene)-cyclohexane-magnesium | 137958-31-7

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 英文名称: 1,2-bis(methylene)-cyclohexane-magnesium
• CAS: 137958-31-7
• 化学式: C₈H₁₂Mg
• 分子量: 132.488
• InChiKey: HNNNUAFQQDDGKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  9.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  1,2-bis(methylene)-cyclohexane-magnesium 在 oxonium 作用下， 以 四氢呋喃 为溶剂， 生成 2-Methyl-3-(1-methyl-2-methylenecyclohexyl)-(S)-1,2-propanediol
  参考文献：
  名称：

  由环氧化物和1,3-二烯制备醇和1,2-二醇

  摘要：

  使用活性镁，环氧化物和1,3-二烯的一锅法合成可以高收率地形成包含季碳中心的醇和1,2-二醇。

  DOI：

  10.1016/s0040-4039(00)61714-8
• 作为产物：
  描述：

  1,2-二甲撑环己烷 在 萘 、 lithium 、 magnesium chloride 作用下， 生成 1,2-bis(methylene)-cyclohexane-magnesium
  参考文献：
  名称：

  Direct synthesis of spiro δ-lactones from conjugated dienes and epoxides

  摘要：

  Stepwise reactions of conjugated diene-magnesium reagents with an epoxide followed by carbon dioxide provide a direct method for a one-pot synthesis of spiro delta-lactones accommodating a vinyl moiety at the beta-position.

  DOI：

  10.1016/s0040-4039(00)61713-6

文献信息

• Reactions of magnesium complexes of 1,2-dimethylenecycloalkanes with carboxylic esters: the formation of a versatile intermediate capable of generating fused rings or .beta.,.gamma.-unsaturated ketones
  作者：Heping Xiong、Reuben D. Rieke

  DOI：10.1021/ja00037a066

  日期：1992.5
• One-step spiroannulation using 1,2-bis(methylene)cycloalkane-magnesium reagents
  作者：Reuben D. Rieke、Heping Xiong

  DOI：10.1021/jo00050a036

  日期：1992.11

  A one-step method for the synthesis of a wide variety of spirocyclic systems has been developed based on the reactions of bis-electrophiles with a series of new 1,3-diene-magnesium reagents, the magnesium complexes of 1,2-bis(methylene)cycloalkanes. The direct metalation of 1,2-bis(methylene)cycloalkanes with highly reactive magnesium in THF at ambient temperature generates the corresponding diene-magnesium reagents in high yields. Reactions of the diene-magnesium reagents with 1,n-dibromoalkanes produce a large number of spirocarbocycles containing an exocyclic double bond. The ring sizes of the accessible spiro compounds can be any combinations of four- to seven-membered rings. In most cases, the initially alkylated intermediates can be trapped by protonation, giving the corresponding bromo olefins. Significantly, treatment of the diene-magnesium reagents with bromoalkyl nitriles leads to a one-step synthesis of keto-functionalized spirocycles. The initial adduct is believed to be a Grignard reagent containing a cyano group. When a bromo nitrile containing a cyclic moiety is used as the bis-electrophile, the approach provides a direct access to dispiroenones.
• Synthesis of spiro .gamma.-lactones from conjugated dienes
  作者：Heping Xiong、Reuben D. Rieke

  DOI：10.1021/jo00052a004

  日期：1992.12

  Stepwise reactions of conjugated dienemagnesium reagents with a ketone at -78-degrees-C, followed by carbon dioxide at 0-degrees-C to room temperature, provide a one-pot method for the synthesis of spiro gamma-lactones containing a vinyl group at the beta-position.