2,2-dimethyl-5-hexen-1-ol tosylate | 89745-98-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2-dimethyl-5-hexen-1-ol tosylate
• 英文别名: 2,2-Dimethylhex-5-en-1-yl 4-methylbenzene-1-sulfonate；2,2-dimethylhex-5-enyl 4-methylbenzenesulfonate
• CAS: 89745-98-2
• 化学式: C₁₅H₂₂O₃S
• 分子量: 282.404
• InChiKey: UHTBGOFQHMUIEJ-UHFFFAOYSA-N

物化性质

• 沸点：
  394.3±21.0 °C(Predicted)
• 密度：
  1.067±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-5-hexen-1-ol tosylate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 96.0h， 以11%的产率得到5,5-二甲基-1-己烯
  参考文献：
  名称：

  Occurrence of electron transfer in the reduction of organic halides by lithium aluminum hydride and aluminum hydride

  摘要：

  DOI：

  10.1021/jo00193a019
• 作为产物：
  描述：

  5-氯-5-甲基己-1-烯 在 吡啶 、 lithium aluminium tetrahydride 、 magnesium 作用下， 以 乙醚 、 苯 为溶剂， 反应 24.0h， 生成 2,2-dimethyl-5-hexen-1-ol tosylate
  参考文献：
  名称：

  Occurrence of electron transfer in the reduction of organic halides by lithium aluminum hydride and aluminum hydride

  摘要：

  DOI：

  10.1021/jo00193a019

文献信息

• 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。
• Competing radical, carbanion, and carbene pathways in the reactions of hindered primary alkyl halides with lithium dialkylamides
  作者：E. C. Ashby、B. Park、G. S. Patil、K. Gadru、R. Gurumurthy

  DOI：10.1021/jo00054a028

  日期：1993.1

  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.
• ASHBY, E. C.;ARGYROPOULOS, J. N., TETRAHEDRON LETT., 1984, 25, N 1, 7-10
  作者：ASHBY, E. C.、ARGYROPOULOS, J. N.

  DOI：——

  日期：——
• ASHBY, E. C.;PARK, W. S.;GOEL, A. B.;SU, WEI-YANG, J. ORG. CHEM., 1985, 50, N 25, 5184-5193
  作者：ASHBY, E. C.、PARK, W. S.、GOEL, A. B.、SU, WEI-YANG

  DOI：——

  日期：——
• ASHBY, E. C.;DEPRIEST, R. N.;GOEL, A. B.;WENDEROTH, B.;PHAM, TUNG, N., J. ORG. CHEM., 1984, 49, N 19, 3545-3556
  作者：ASHBY, E. C.、DEPRIEST, R. N.、GOEL, A. B.、WENDEROTH, B.、PHAM, TUNG, N.

  DOI：——

  日期：——