<3,3-(2)H2>octyl bromide | 86412-17-1

• 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: <3,3-(2)H2>octyl bromide
• 英文别名: (3,3-(2)H2)octyl bromide；1-bromo-3,3-dideuteriooctane
• CAS: 86412-17-1
• 化学式: C₈H₁₇Br
• 分子量: 195.111
• InChiKey: VMKOFRJSULQZRM-NCYHJHSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  9.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  苯甲酰氯 、 <3,3-(2)H2>octyl bromide 在 magnesium 、 二氯二茂锆 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 3.5h， 以50%的产率得到
  参考文献：
  名称：

  Transformation of Zirconocene−Olefin Complexes into Zirconocene Allyl Hydride and Their Use as Dual Nucleophilic Reagents:  Reactions with Acid Chloride and 1,4-Diketone

  摘要：

  Zirconocene-olefin complexes Cp2Zr(H2C=CHR), prepared in benzene-THF at 0 degreesC, react with acid chlorides to provide homoallylic alcohols. The key is an equilibrium between the zirconocene-olefin complexes and the corresponding zirconocene allyl hydride complexes via allylic C-H bond cleavage of the coordinating alkenes. Furthermore, the zirconocene-olefin complexes are also available for the reaction with 1,4-diketone to afford anti-1,4-diols with excellent diastereoselectivity. Thus, Cp2Zr(H2C CHR) serves as a donor of both hydride and an allylic group. These reactions also proceed efficiently by using zirconocene-olefin complexes, derived from Cp2ZrCl2, Mg metal, and 1-alkenes.

  DOI：

  10.1021/ja049184y
• 作为产物：
  描述：

  1-bromo-1,1-dideuteriohexane 在 吡啶 、 六甲基磷酰三胺 、 lithium aluminium tetrahydride 、 lithium bromide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 丙酮 为溶剂， 生成 <3,3-(2)H2>octyl bromide
  参考文献：
  名称：

  Transformation of Zirconocene−Olefin Complexes into Zirconocene Allyl Hydride and Their Use as Dual Nucleophilic Reagents:  Reactions with Acid Chloride and 1,4-Diketone

  摘要：

  Zirconocene-olefin complexes Cp2Zr(H2C=CHR), prepared in benzene-THF at 0 degreesC, react with acid chlorides to provide homoallylic alcohols. The key is an equilibrium between the zirconocene-olefin complexes and the corresponding zirconocene allyl hydride complexes via allylic C-H bond cleavage of the coordinating alkenes. Furthermore, the zirconocene-olefin complexes are also available for the reaction with 1,4-diketone to afford anti-1,4-diols with excellent diastereoselectivity. Thus, Cp2Zr(H2C CHR) serves as a donor of both hydride and an allylic group. These reactions also proceed efficiently by using zirconocene-olefin complexes, derived from Cp2ZrCl2, Mg metal, and 1-alkenes.

  DOI：

  10.1021/ja049184y

文献信息

• Boden, Neville; Bushby, Richard J.; Clark, Leslie D., Journal of the Chemical Society. Perkin transactions I, 1983, p. 543 - 551
  作者：Boden, Neville、Bushby, Richard J.、Clark, Leslie D.

  DOI：——

  日期：——
• BODEN, N.;BUSHBY, R. J.;CLARK, L. D., J. CHEM. SOC. PERKIN TRANS., 1983, N 3, 543-551
  作者：BODEN, N.、BUSHBY, R. J.、CLARK, L. D.

  DOI：——

  日期：——