syn-4-bromo-3,6-dimethyl-4-cyclohexene-1,1,2,2-tetracarbonitrile

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: syn-4-bromo-3,6-dimethyl-4-cyclohexene-1,1,2,2-tetracarbonitrile
• 英文别名: (3R,6R)-4-bromo-3,6-dimethylcyclohex-4-ene-1,1,2,2-tetracarbonitrile
• 化学式: C₁₂H₉BrN₄
• 分子量: 289.134
• InChiKey: QMLLFSAKTNNWLT-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  95.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-甲基-2,3-戊二烯-1-醇 在 吡啶 、 palladium diacetate 、 lithium bromide 作用下， 以 溶剂黄146 、 丙酮 为溶剂， 反应 20.0h， 生成 syn-4-bromo-3,6-dimethyl-4-cyclohexene-1,1,2,2-tetracarbonitrile
  参考文献：
  名称：

  Palladium(II)-Catalyzed S_N2‘ Reactions of α-Allenic Acetates. Stereoconvergent Synthesis of (Z,E)-2-Bromo-1,3-dienes

  摘要：

  The reaction of acetylated a-allenic alcohols with LiBr in the presence of 1.5 mol % of Pd(OAc)(2) provides easy access to substituted (Z,E)-2-bromo-1,3-dienes in good yields with excellent diastereoselectivity. Both secondary and tertiary acetates as well as terminal and nonterminal allenes were studied to investigate the scope and the limitations of the reaction. A mechanism is proposed to clarify how a diastereomeric mixture of the starting compound is transformed into a single diastereomer of the product.

  DOI：

  10.1021/jo015950x

文献信息

• Palladium(II)-Catalyzed S_N2‘ Reactions of α-Allenic Acetates. Stereoconvergent Synthesis of (<i>Z</i>,<i>E</i>)-2-Bromo-1,3-dienes
  作者：Attila Horváth、Jan-E. Bäckvall

  DOI：10.1021/jo015950x

  日期：2001.11.1

  The reaction of acetylated a-allenic alcohols with LiBr in the presence of 1.5 mol % of Pd(OAc)(2) provides easy access to substituted (Z,E)-2-bromo-1,3-dienes in good yields with excellent diastereoselectivity. Both secondary and tertiary acetates as well as terminal and nonterminal allenes were studied to investigate the scope and the limitations of the reaction. A mechanism is proposed to clarify how a diastereomeric mixture of the starting compound is transformed into a single diastereomer of the product.