1,4-dideutero-1-bromoocta-2,5-diyne | 1526974-01-5

• 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: 1,4-dideutero-1-bromoocta-2,5-diyne
• CAS: 1526974-01-5
• 化学式: C₈H₉Br
• 分子量: 187.048
• InChiKey: MBUCOKBZJPDVNZ-VBCVTXNDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.19
• 重原子数：
  9.0
• 可旋转键数：
  0.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  1,4-dideutero-1-bromoocta-2,5-diyne 在 sodium tetrahydroborate 、 copper(l) iodide 、 氢气 、 nickel(II) acetate tetrahydrate 、 potassium carbonate 、 sodium iodide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0~70.0 ℃ 、101.33 kPa 条件下， 反应 18.0h， 生成 11,14-dideutero-cis,cis,cis-octadeca-9,12,15-trienoic acid ethyl ester
  参考文献：
  名称：

  Unusual Kinetic Isotope Effects of Deuterium Reinforced Polyunsaturated Fatty Acids in Tocopherol-Mediated Free Radical Chain Oxidations

  摘要：

  Substitution of -CD2- at the reactive centers of linoleic and linolenic acids reduces the rate of abstraction of D by a tocopheryl radical by as much as 36-fold, compared to the abstraction of H from a corresponding -CH2- center. This H. atom transfer reaction is the rate-determining step in the tocopherol-mediated peroxidation of lipids in human low-density lipoproteins, a process that has been linked to coronary artery disease. The unanticipated large kinetic isotope effects reported here for the tocopherol-mediated oxidation of linoleic and linolenic acids and esters suggests that tunneling makes this process favorable.

  DOI：

  10.1021/ja410569g
• 作为产物：
  描述：

  1,4-dideuteroocta-2,5-diyn-1-ol 在 吡啶 、 三溴化磷 作用下， 以 乙醚 为溶剂， 反应 3.5h， 以58%的产率得到1,4-dideutero-1-bromoocta-2,5-diyne
  参考文献：
  名称：

  Unusual Kinetic Isotope Effects of Deuterium Reinforced Polyunsaturated Fatty Acids in Tocopherol-Mediated Free Radical Chain Oxidations

  摘要：

  Substitution of -CD2- at the reactive centers of linoleic and linolenic acids reduces the rate of abstraction of D by a tocopheryl radical by as much as 36-fold, compared to the abstraction of H from a corresponding -CH2- center. This H. atom transfer reaction is the rate-determining step in the tocopherol-mediated peroxidation of lipids in human low-density lipoproteins, a process that has been linked to coronary artery disease. The unanticipated large kinetic isotope effects reported here for the tocopherol-mediated oxidation of linoleic and linolenic acids and esters suggests that tunneling makes this process favorable.

  DOI：

  10.1021/ja410569g