(E)-methyl 3-methyl-6-oxohept-2-enoate

• 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)-methyl 3-methyl-6-oxohept-2-enoate
• 英文别名: methyl (E)-3-methyl-6-oxohept-2-enoate
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: ONIWNNSPFQEXDV-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  丁烯酮 、 2-丁炔酸甲酯 在 bis(1,5-cyclooctadiene)nickel (0) 、 三丁基膦 三乙基硼 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 以74%的产率得到(E)-methyl 3-methyl-6-oxohept-2-enoate
  参考文献：
  名称：

  Catalytic Intermolecular Reductive Coupling of Enones and Alkynes

  摘要：

  A nickel-catalyzed intermolecular reductive coupling of enones and alkynes has been developed as a novel entry to gamma,delta-unsaturated ketones. The process does not require formation of a vinyl organometallic, and a variety of functional groups including free hydroxyls and esters are tolerated. A number of features that complement existing copper-mediated processes are highlighted.

  DOI：

  10.1021/ja073300q

文献信息

• Catalytic Intermolecular Reductive Coupling of Enones and Alkynes
  作者：Ananda Herath、Benjamin B. Thompson、John Montgomery

  DOI：10.1021/ja073300q

  日期：2007.7.1

  A nickel-catalyzed intermolecular reductive coupling of enones and alkynes has been developed as a novel entry to gamma,delta-unsaturated ketones. The process does not require formation of a vinyl organometallic, and a variety of functional groups including free hydroxyls and esters are tolerated. A number of features that complement existing copper-mediated processes are highlighted.
• Evolution of Efficient Strategies for Enone−Alkyne and Enal−Alkyne Reductive Couplings
  作者：Wei Li、Ananda Herath、John Montgomery

  DOI：10.1021/ja9083607

  日期：2009.11.25

  Strategies for the reductive coupling of enones or enals with alkynes have been developed. The reducing agents employed include organozincs, organoboranes, organosilanes, and methanol. The latter of these strategies is simple, cost-effective, and tolerant of many functional groups. Isotopic labeling strategies have provided supporting evidence for the mechanistic proposals.