(L)-Menthyl trans-hept-2-enoate-7-al | 144800-83-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (L)-Menthyl trans-hept-2-enoate-7-al
• CAS: 144800-83-9
• 化学式: C₁₇H₂₈O₃
• 分子量: 280.408
• InChiKey: QUXLTZNODDFIRE-SHVNWIDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (L)-Menthyl trans-hept-2-enoate-7-al 在 盐酸羟胺 、 sodium acetate 作用下， 以 水 、 乙腈 为溶剂， 反应 5.0h， 以79%的产率得到(L)-Menthyl trans-hept-2-enoate-7-al oxime
  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：

  (1R,2S,5R)-menthol bromoacetate 在 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 (L)-Menthyl trans-hept-2-enoate-7-al
  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

• 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.
  作者：Ronald Grigg、Jasothara Markandu、Trevor Perrior、Sivagnanasundram Surendrakumar、William J. Warnock

  DOI：10.1016/s0040-4020(01)89883-5

  日期：1992.1

  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.