2,2-dimethylhexyl p-toluenesulfonate | 60697-64-5

• 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-dimethylhexyl p-toluenesulfonate
• 英文别名: tosylate of 2,2-dimethyl-1-hexanol；2,2-Dimethylhexyl 4-methylbenzenesulfonate
• CAS: 60697-64-5
• 化学式: C₁₅H₂₄O₃S
• 分子量: 284.42
• InChiKey: RMEUSZNXUOZXOV-UHFFFAOYSA-N

物化性质

• 熔点：
  25-27 °C
• 沸点：
  382.2±11.0 °C(Predicted)
• 密度：
  1.055±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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-dimethylhexyl p-toluenesulfonate 在 lithium aluminium deuteride 作用下， 以 四氢呋喃 为溶剂， 反应 96.0h， 以27%的产率得到1-deutero-2,2-dimethylhexane
  参考文献：
  名称：

  Convincing Evidence, Not Involving Cyclizable Radical Probes, That the Reaction of LiAlH₄ with Hindered Alkyl Iodides Proceeds Predominantly by a Single Electron Transfer Pathway^,

  摘要：

  Previous workers have maintained that evidence for the radical nature of the reaction of LiAlH4 with sterically hindered alkyl iodides is due to radical initiation by impurities followed by a halogen atom radical chain process involving the cyclizable alkyl iodide probe and that the reduction of the C-I bond actually proceeds by an S(N)2 pathway. In order to resolve the validity of this explanation, 1-iodo-2,2-dimethylhexane (the saturated counterpart of the cyclizable probe), which is not capable of this halogen atom radical chain process, was allowed to react with LiAlD4. The reduction product, 2,2-dimethylhexane, contained only 4-76% deuterium depending on the conditions of the reaction. This result is consistent with the reaction proceeding by a SET process via a radical intermediate and is inconsistent with an S(N)2 pathway. We have determined the influence of the nature of the reaction on the type of reactor surface (Pyrex, Teflon, stainless steel, and quartz) used in the reaction. We have also studied the influence of AlD3 (a byproduct in the reduction) in the mechanistic evaluation of this reaction.

  DOI：

  10.1021/jo961651+
• 作为产物：
  描述：

  神经酰胺,1-O-[O-(N-乙酰基-a-神经氨基亚酰)-(2&reg3)-O-b-D-吡喃半乳糖基-(1&reg3)-O-2-(乙酰基氨基)-2-脱氧-b-D-吡喃葡萄糖基-(1&reg3)-O-b-D-吡喃半乳糖基-(1&reg4)-b-D-吡喃葡萄糖基]- 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 26.0h， 生成 2,2-dimethylhexyl p-toluenesulfonate
  参考文献：
  名称：

  Convincing Evidence, Not Involving Cyclizable Radical Probes, That the Reaction of LiAlH₄ with Hindered Alkyl Iodides Proceeds Predominantly by a Single Electron Transfer Pathway^,

  摘要：

  Previous workers have maintained that evidence for the radical nature of the reaction of LiAlH4 with sterically hindered alkyl iodides is due to radical initiation by impurities followed by a halogen atom radical chain process involving the cyclizable alkyl iodide probe and that the reduction of the C-I bond actually proceeds by an S(N)2 pathway. In order to resolve the validity of this explanation, 1-iodo-2,2-dimethylhexane (the saturated counterpart of the cyclizable probe), which is not capable of this halogen atom radical chain process, was allowed to react with LiAlD4. The reduction product, 2,2-dimethylhexane, contained only 4-76% deuterium depending on the conditions of the reaction. This result is consistent with the reaction proceeding by a SET process via a radical intermediate and is inconsistent with an S(N)2 pathway. We have determined the influence of the nature of the reaction on the type of reactor surface (Pyrex, Teflon, stainless steel, and quartz) used in the reaction. We have also studied the influence of AlD3 (a byproduct in the reduction) in the mechanistic evaluation of this reaction.

  DOI：

  10.1021/jo961651+

文献信息

• Convincing Evidence, Not Involving Cyclizable Radical Probes, That the Reaction of LiAlH₄ with Hindered Alkyl Iodides Proceeds Predominantly by a Single Electron Transfer Pathway^,
  作者：E. C. Ashby、Catherine O. Welder

  DOI：10.1021/jo961651+

  日期：1997.5.1

  Previous workers have maintained that evidence for the radical nature of the reaction of LiAlH4 with sterically hindered alkyl iodides is due to radical initiation by impurities followed by a halogen atom radical chain process involving the cyclizable alkyl iodide probe and that the reduction of the C-I bond actually proceeds by an S(N)2 pathway. In order to resolve the validity of this explanation, 1-iodo-2,2-dimethylhexane (the saturated counterpart of the cyclizable probe), which is not capable of this halogen atom radical chain process, was allowed to react with LiAlD4. The reduction product, 2,2-dimethylhexane, contained only 4-76% deuterium depending on the conditions of the reaction. This result is consistent with the reaction proceeding by a SET process via a radical intermediate and is inconsistent with an S(N)2 pathway. We have determined the influence of the nature of the reaction on the type of reactor surface (Pyrex, Teflon, stainless steel, and quartz) used in the reaction. We have also studied the influence of AlD3 (a byproduct in the reduction) in the mechanistic evaluation of this reaction.