1-(iodomethyl)-3,3-dimethylcyclopentane | 113934-07-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机碘化物
• 英文名称: 1-(iodomethyl)-3,3-dimethylcyclopentane
• 英文别名: 3-(Iodomethyl)-1,1-dimethylcyclopentane
• CAS: 113934-07-9
• 化学式: C₈H₁₅I
• 分子量: 238.112
• InChiKey: RQPRVHIHOGLNEX-UHFFFAOYSA-N

物化性质

• 沸点：
  209.2±9.0 °C(Predicted)
• 密度：
  1.425±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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-(iodomethyl)-3,3-dimethylcyclopentane 在 lithium aluminium deuteride 作用下， 以 四氢呋喃 为溶剂， 以99%的产率得到1,1-二甲基-3-(甲基-d)环戊烷
  参考文献：
  名称：

  使用自由基探针确定SET的有效性问题。卤代烷与LiAlH 4的反应。

  摘要：

  近来，人们质疑使用可环化的烷基碘作为自由基探针与LiAlH 4和其他亲核试剂反应的有效性。先前提供的数据以及此处提供的新数据都清楚地表明，在研究的反应中形成的环化产物确实是通过涉及自由基前体的电子转移过程而形成的。

  DOI：

  10.1016/s0040-4039(00)95470-4
• 作为产物：
  描述：

  2,2-二甲基-5-己烯-1-醇 在 吡啶 、 六苯基二锡 、 碘 、 三苯基膦 作用下， 以 苯 为溶剂， 反应 39.0h， 生成 1-(iodomethyl)-3,3-dimethylcyclopentane
  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

• Occurrence of electron transfer in the reduction of organic halides by lithium aluminum hydride and aluminum hydride
  作者：Edward C. Ashby、R. N. DePriest、A. B. Goel、B. Wenderoth、T. N. Pham

  DOI：10.1021/jo00193a019

  日期：1984.9
• Single electron transfer mechanism in the reaction of 1,3-dithianyllithium and alkyl iodides
  作者：Eusebio Juaristi、Hugo A. Jimenez-Vazquez

  DOI：10.1021/jo00004a051

  日期：1991.2

  The reaction between 2-lithio-1,3-dithiane and optically active (R)-2-iodooctane was found to proceed with complete inversion of configuration. This result suggests that the S(N)2 (rather than single electron transfer (SET) mechanism is the preferred pathway for reaction between dithianyllithium and unhindered alkyl halides. When the neopentyl-type radical probe 5,5-dimethyl-6-iodo-1-hexene was used as the substrate halide, 6-11% cyclized alkylated product was obtained. This result suggests that when the S(N)2 pathway is blocked, SET mechanisms become operative to some extent, at least with iodide as the halogen. The reaction of dithianyllithium and (R)-2-iodooctane and 5,5-dimethyl-6-iodo-1-hexene, with hexane as the solvent, proceeds under heterogeneous conditions to bring about complete racemization or cyclization of the respective iodide. These results demonstrate for the first time that 2-lithio-1,3-dithiane can act as electron donor in reactions initiated by electron transfer to alkyl iodides.
• A Photochemical Probe for Single Electron Transfer in Nucleophilic Aliphatic Substitution: Evidence for Geminate Radical Coupling in the Solvent Cage
  作者：Laren M. Tolbert、Xiao-Jing Sun、E. C. Ashby

  DOI：10.1021/ja00115a001

  日期：1995.3

  A major effort to establish single electron transfer (SET) as an important pathway in nucleophilic aliphatic subsitution reactions has involved the use of cyclizable probes, e.g., 6-iodo-5,5-dimethyl-1-hexene. In order to examine the partition between cyclization and direct radical-radical recombination, we have investigated the ground-state and excited-state chemistry of the 9-phenylfluorenyl anion (9PF(-)) with neopentyl-type iodides. It has been shown that 9PF(-) does not react with Me(3)CCH(2)I, but it does undergo efficient reaction upon irradiation (Phi = 1.0) to yield nucleophilic aliphatic substitution products, With the sterically analogous cyclizable probe 6-iodo-5,5-dimethyl-1-hexene, no ground-state reaction is observed, However, both cyclized and uncyclized products of substitution, 9PFR(c) and 9PFR(u), are produced upon irradiation. Thus photoproducts clearly involving electron-transfer-induced radical intermediates can result without acommpanying free-radical cyclization. These results suggest that, although the observation of cyclized products in the reaction of a cyclizable radical probe with a nucleophile is evidence of a radical intermediate, the absence of such cyclized products does not require the absence of radical intermediates.
• ASHBY, E. C.;PARK, BONGJIN, ACTA CHEM. SCAND., 44,(1990) N, C. 291-293
  作者：ASHBY, E. C.、PARK, BONGJIN

  DOI：——

  日期：——
• JUARISTI, EUSEBIO;JIMENEZ-VAZQUEZ, HUGO A., J. ORG. CHEM., 56,(1991) N, C. 1623-1630
  作者：JUARISTI, EUSEBIO、JIMENEZ-VAZQUEZ, HUGO A.

  DOI：——

  日期：——