(E)-tert-butyl 8-cyano-2-methyl-7-oxooct-2-enoate | 1431792-30-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-tert-butyl 8-cyano-2-methyl-7-oxooct-2-enoate
• CAS: 1431792-30-1
• 化学式: C₁₄H₂₁NO₃
• 分子量: 251.326
• InChiKey: ISDNNGGEEPPDHW-YRNVUSSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  67.16
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (E)-tert-butyl 8-cyano-2-methyl-7-oxooct-2-enoate 在 吡啶 、 1H-咪唑-1-磺酰叠氮 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以53%的产率得到
  参考文献：
  名称：

  α-Diazo-β-ketonitriles: Uniquely Reactive Substrates for Arene and Alkene Cyclopropanation

  摘要：

  An investigation of the intramolecular cyclopropanation reactions of alpha-diazo-beta-ketonitriles is reported. These studies reveal that alpha-diazo-beta-ketonitriles exhibit unique reactivity in their ability to undergo arene cyclopropanation reactions; other similar acceptor acceptor-substituted diazo substrates instead produce mixtures of C-H insertion and dimerization products. alpha-Diazo-beta-ketonitriles also undergo highly efficient intramolecular cyclopropanation of tri- and tetrasubstituted alkenes. In addition, the alpha-cyano-alpha-ketocyclopropane products are demonstrated to serve as substrates for S(N)2, S(N)2', and aldehyde cycloaddition reactions.

  DOI：

  10.1021/ja401610p
• 作为产物：
  描述：

  3-bromo-2-methyl-acrylic acid tert-butyl ester 在 2-双环己基膦-2',6'-二甲氧基联苯 、 palladium diacetate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.16h， 生成 (E)-tert-butyl 8-cyano-2-methyl-7-oxooct-2-enoate
  参考文献：
  名称：

  α-Diazo-β-ketonitriles: Uniquely Reactive Substrates for Arene and Alkene Cyclopropanation

  摘要：

  An investigation of the intramolecular cyclopropanation reactions of alpha-diazo-beta-ketonitriles is reported. These studies reveal that alpha-diazo-beta-ketonitriles exhibit unique reactivity in their ability to undergo arene cyclopropanation reactions; other similar acceptor acceptor-substituted diazo substrates instead produce mixtures of C-H insertion and dimerization products. alpha-Diazo-beta-ketonitriles also undergo highly efficient intramolecular cyclopropanation of tri- and tetrasubstituted alkenes. In addition, the alpha-cyano-alpha-ketocyclopropane products are demonstrated to serve as substrates for S(N)2, S(N)2', and aldehyde cycloaddition reactions.

  DOI：

  10.1021/ja401610p