3,3-dimethyl-1-methylenecyclopentane | 78343-76-7

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 3,3-dimethyl-1-methylenecyclopentane
• 英文别名: 1,1-Dimethyl-3-methylidenecyclopentane
• CAS: 78343-76-7
• 化学式: C₈H₁₄
• 分子量: 110.199
• InChiKey: HHVJYBCGWZUROZ-UHFFFAOYSA-N

物化性质

• 沸点：
  112.0±7.0 °C(Predicted)
• 密度：
  0.80±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  6-碘-5,5-二甲基己-1-烯 在 六苯基二锡 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 63.0h， 生成 3,3-dimethyl-1-methylenecyclopentane
  参考文献：
  名称：

  Competing radical, carbanion, and carbene pathways in the reactions of hindered primary alkyl halides with lithium dialkylamides

  摘要：

  A variety of methods were utilized to study the mechanism of reaction of 6-iodo-5,5-dimethyl-1-hexene and its bromo, chloro, and tosylate derivatives with LDA and several other lithium dialkylamides. In the reaction of 6-iodo-5,5-dimethyl-1-hexene with LDA in THF, radical, carbanion, and carbene pathways occurred simultaneously. However, when the corresponding bromide was allowed to react with LDA, the radical pathway was minor and when the corresponding chloride or tosylate was allowed to react with LDA, no evidence for radical products was observed. This is the first time that competing radical, carbanion, and carbene pathways have been detected in the reaction of a primary alkyl halide with any nucleophile.

  DOI：

  10.1021/jo00054a028

文献信息

• Evidence for single electron transfer in the reaction of alkoxides with alkyl halides
  作者：E.C. Ashby、Dong-Hak Bae、Won-Suh Park、Robert N. Depriest、Wei-Yang Su

  DOI：10.1016/s0040-4039(01)81536-7

  日期：1984.1

  Evidence for a radical process in the reaction of lithium alkoxides with alkyl iodides was obtained by the observation of cyclization of appropriate radical probes, by the trapping of radicals, and by EPR spectroscopic observations relating to the one electron donor properties of alkoxides.

  通过观察合适的自由基探针的环化，自由基的捕获以及与醇盐的单电子给体性质有关的EPR光谱观察，获得了锂醇盐与烷基碘化物反应中自由基过程的证据。
• Evidence for single electron transfer in the reaction of a lithium enolate with a primary alkyl iodide
  作者：E.C. Ashby、J.N. Argyropoulos

  DOI：10.1016/s0040-4039(01)91134-7

  日期：1984.1

  Evidence for a radical process in the reaction of the lithium enolate of propiophenone with a primary alkyl iodide was obtained by the observation of cyclization of an appropriate radical probe, by the trapping of the radical intermediate and by the comparison of the relative rates of reactions of the probe alkyl iodide with the corresponding bromide and tosylate.

  通过观察合适的自由基探针的环化，捕获自由基中间体并比较三乙胺的相对反应速率，获得了苯乙酮的烯醇锂与伯烷基碘的反应中发生自由基过程的证据。探针烷基碘与相应的溴化物和甲苯磺酸酯。
• Organometallic reaction mechanisms. 17. Nature of alkyl transfer in reactions of Grignard reagents with ketones. Evidence for radical intermediates in the formation of 1,2-addition product involving tertiary and primary Grignard reagents
  作者：E. C. Ashby、Joseph R. Bowers

  DOI：10.1021/ja00399a018

  日期：1981.5
• Evidence for single electron transfer in the reations of alkali metal amides and alkoxides with alkyl halides and polynuclear hydrocarbons
  作者：E. C. Ashby、A. B. Goel、R. N. DePriest

  DOI：10.1021/jo00324a056

  日期：1981.5
• Single electron transfer in the reaction of enolates with alkyl halides
  作者：E. C. Ashby、J. N. Argyropoulos

  DOI：10.1021/jo00218a007

  日期：1985.9