5-Carbomethoxymethylpyrroline 1-oxide | 144800-80-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-Carbomethoxymethylpyrroline 1-oxide
• 英文别名: methyl 2-(1-oxido-3,4-dihydro-2H-pyrrol-1-ium-2-yl)acetate
• CAS: 144800-80-6
• 化学式: C₇H₁₁NO₃
• 分子量: 157.169
• InChiKey: GUCTVBCXOWGITB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.29
• 重原子数：
  11.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  52.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-甲基马来酰亚胺 、 5-Carbomethoxymethylpyrroline 1-oxide 以 氘代甲苯 为溶剂， 反应 15.0h， 以50%的产率得到((3aR,6S,8aS,8bS)-2-Methyl-1,3-dioxo-octahydro-dipyrrolo[1,2-b;3',4'-d]isoxazol-6-yl)-acetic acid methyl ester
  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：

  methyl (E)-6-hydroxyhex-2-enoate 在 盐酸羟胺 、 sodium acetate 作用下， 以 水 、 乙腈 为溶剂， 以51%的产率得到5-Carbomethoxymethylpyrroline 1-oxide
  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

• Confirmation of the structure of (±)-preisomide by total synthesis
  作者：Hong Kang Teo、Patcharaporn Sae-Lao、Roderick W. Bates

  DOI：10.1039/d3ob01250f

  日期：——

  The structure of preisomide has been confirmed by total synthesis involving chemoselective oxazine formation and vinyl iodide carbonylation in six steps (longest linear sequence) and 23% overall yield.

  preisomide 的结构已通过全合成得到证实，包括化学选择性恶嗪形成和碘乙烯羰基化，分六步（最长线性序列），总产率为 23%。