1-(3-bromo-n-propyl)-1-methyl-2-methylenecyclohexane | 137958-33-9

• 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-(3-bromo-n-propyl)-1-methyl-2-methylenecyclohexane
• 英文别名: 1-(3-Bromopropyl)-1-methyl-2-methylidenecyclohexane
• CAS: 137958-33-9
• 化学式: C₁₁H₁₉Br
• 分子量: 231.176
• InChiKey: ZZOUOGCGPUHDLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1,2-二甲撑环己烷 在 oxonium 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 1-(3-bromo-n-propyl)-1-methyl-2-methylenecyclohexane
  参考文献：
  名称：

  One-step spiroannulation using 1,2-bis(methylene)cycloalkane-magnesium reagents

  摘要：

  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.

  DOI：

  10.1021/jo00050a036

文献信息

• The magnesium complexes of 1,2-dimethylenecycloalkanes: a new method for a one-step spiroannelation
  作者：Heping Xiong、Reuben D. Rieke

  DOI：10.1016/s0040-4039(00)92361-x

  日期：1991.9

  Reactions of new dienemagnesium reagents prepared from highly reactive magnesium and 1,2-dimethylenecycloalkanes with 1,n-dibromoalkanes and bromoalkylnitriles provide a one-step method for the synthesis of commonly encountered spirocyclic systems.