ethyl 5,6-dimethylhept-5-enoate | 65502-54-7

• 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: ethyl 5,6-dimethylhept-5-enoate
• 英文别名: Ethyl-5,6-dimethylhept-5-enoat
• CAS: 65502-54-7
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: OOYLIGNEGRQNEL-UHFFFAOYSA-N

物化性质

• 沸点：
  237.2±19.0 °C(Predicted)
• 密度：
  0.891±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 5,6-dimethylhept-5-enoate 在 吡啶 、 1H-咪唑-1-磺酰叠氮 、 bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 4.5h， 生成 6,7,7-trimethyl-2-oxobicyclo[4.1.0]heptane-1-carbonitrile
  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：

  4-ethoxy-4-oxobutylzinc bromide lithium chloride 、 2-溴-3-甲基-2-丁烯 在 2-双环己基膦-2',6'-二甲氧基联苯 、 palladium diacetate 作用下， 以 四氢呋喃 为溶剂， 反应 2.58h， 以76%的产率得到ethyl 5,6-dimethylhept-5-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

文献信息

• Beckwith,A.L.J.; Moad,G., Australian Journal of Chemistry, 1977, vol. 30, p. 2733 - 2739
  作者：Beckwith,A.L.J.、Moad,G.

  DOI：——

  日期：——
• BECKWITH A. L. J.; MOAD G., AUSTRAL. J. CHEM., 1977, 30, NO 12, 2733-2739
  作者：BECKWITH A. L. J.、 MOAD G.

  DOI：——

  日期：——
• α-Diazo-β-ketonitriles: Uniquely Reactive Substrates for Arene and Alkene Cyclopropanation
  作者：Roger R. Nani、Sarah E. Reisman

  DOI：10.1021/ja401610p

  日期：2013.5.15

  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.