2-Heptenoic acid, 7-(hydroxyimino)-, methyl ester, (E,E)- | 113410-59-6

• 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: 2-Heptenoic acid, 7-(hydroxyimino)-, methyl ester, (E,E)-
• 英文别名: 2-Heptenoic acid, 7-(hydroxyimino)-, methyl ester；Methyl trans-hept-2-enoate-7-al oxime
• CAS: 113410-59-6；144800-82-8
• 化学式: C₈H₁₃NO₃
• 分子量: 171.196
• InChiKey: FDPDGYVQFHHFOR-NNVXRVHDSA-N

物化性质

• 沸点：
  293.9±33.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.35
• 重原子数：
  12.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  58.89
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-苯基马来酰亚胺 、 2-Heptenoic acid, 7-(hydroxyimino)-, methyl ester, (E,E)- 以 甲苯 为溶剂， 反应 3.0h， 以90%的产率得到
  参考文献：
  名称：

  X = Y - ZH systems as potential 1,3-dipoles part 35. Generation of nitrones from oximes. Class 3 processes. Tandem intramolecular michael addition (1,3-azaprotio cyclotransfer) - intermolecular 1,3-dipolar cycloaddition reactions.

  摘要：

  Aldoximes and ketoximes possessing gamma- or delta-alkenyl substituents undergo thermal conversion to 5- and 6- membered cyclic nitrones via a 1,3-azaprotio cyclotransfer, a 2n + 2-sigma + 2-pi concerted process, rather than a Michael addition. The reactions can be performed as a tandem nitrone formation-cycloaddition sequence or, if required, the intermediate nitrones can be isolated. The cycloadditions usually proceed via an exo-transition state and show both regio- and diastereofacial-specificity. Preliminary attempts at chiral induction via a menthyl auxiliary are reported.

  DOI：

  10.1016/s0040-4020(01)89883-5
• 作为产物：
  描述：

  (E)-7-氧代庚-2-烯酸甲酯 在 盐酸羟胺 、 sodium acetate 作用下， 以 水 、 乙腈 为溶剂， 反应 3.0h， 以72%的产率得到2-Heptenoic acid, 7-(hydroxyimino)-, methyl ester, (E,E)-
  参考文献：
  名称：

  X = Y - ZH systems as potential 1,3-dipoles part 35. Generation of nitrones from oximes. Class 3 processes. Tandem intramolecular michael addition (1,3-azaprotio cyclotransfer) - intermolecular 1,3-dipolar cycloaddition reactions.

  摘要：

  Aldoximes and ketoximes possessing gamma- or delta-alkenyl substituents undergo thermal conversion to 5- and 6- membered cyclic nitrones via a 1,3-azaprotio cyclotransfer, a 2n + 2-sigma + 2-pi concerted process, rather than a Michael addition. The reactions can be performed as a tandem nitrone formation-cycloaddition sequence or, if required, the intermediate nitrones can be isolated. The cycloadditions usually proceed via an exo-transition state and show both regio- and diastereofacial-specificity. Preliminary attempts at chiral induction via a menthyl auxiliary are reported.

  DOI：

  10.1016/s0040-4020(01)89883-5

文献信息

• Tandem intramolecular Michael addition and 1,3-dipolar cycloaddition reactions of oximes; versatile new carbon–carbon bond forming methodology
  作者：Paul Armstrong、Ronald Grigg、Sivagnanasundram Surendrakumar、William J. Warnock

  DOI：10.1039/c39870001327

  日期：——

  Oximes undergo intramolecular Michael addition to proximate electronegative alkenes, generating cyclic nitrones which can be trapped inter- and intra-molecularly in 1,3-dipolar cycloaddition reactions taking place either separately or in tandem.

  肟经过分子内迈克尔加成反应，形成邻近的负电性烯烃，生成环状硝酮，可被分子间和分子内捕获在分别或串联发生的1,3-偶极环加成反应中。