1-bromo-2,2-dimethylhexane | 101419-70-9

• 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-bromo-2,2-dimethylhexane
• 英文别名: 1-bromo-2,2-dimethyl-hexane；2,2-Dimethylhexylbromid
• CAS: 101419-70-9
• 化学式: C₈H₁₇Br
• 分子量: 193.127
• InChiKey: GBNYMCZJWZKJPW-UHFFFAOYSA-N

物化性质

• 沸点：
  182.1±8.0 °C(Predicted)
• 密度：
  1.111±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• 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

• 作为产物：
  描述：

  2,2-二甲基-1-己醇 以36%的产率得到1-bromo-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+

文献信息

• Conformational analysis and stereodynamics of primary acyclic alkyl radicals by EPR spectroscopy
  作者：K. U. Ingold、D. C. Nonhebel、J. C. Walton

  DOI：10.1021/j100404a017

  日期：1986.6
• Herwig,K. et al., Chemische Berichte, 1975, vol. 108, p. 1421 - 1436
  作者：Herwig,K. et al.

  DOI：——

  日期：——
• CATALYTIC METHOD FOR PRODUCING FLUOROAROMATIC COMPOUNDS USING SUBSTITUTED PYRIDINIUM SALTS
  申请人：MALLINCKRODT SPECIALTY CHEMICALS COMPANY

  公开号：EP0252964B1

  公开（公告）日：1991-08-21
• Co-polymerization of an isoolefin with a halogenated co-monomer
  申请人：Lanxess Inc.

  公开号：EP1892254B1

  公开（公告）日：2012-06-06
• US3954832A
  申请人：——

  公开号：US3954832A

  公开（公告）日：1976-05-04