(2E)-2-[1-(3-hydroxypropyl)pyrrolidin-2-ylidene]-N-methoxy-N-methylethanamide | 1162651-00-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2E)-2-[1-(3-hydroxypropyl)pyrrolidin-2-ylidene]-N-methoxy-N-methylethanamide
• CAS: 1162651-00-4
• 化学式: C₁₁H₂₀N₂O₃
• 分子量: 228.291
• InChiKey: ULORZOWIZBZXRK-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.37
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  53.01
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2E)-2-[1-(3-hydroxypropyl)pyrrolidin-2-ylidene]-N-methoxy-N-methylethanamide 在 咪唑 、 碘 、 三苯基膦 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 1.0h， 以64%的产率得到N-methoxy-N-methyl-1,2,3,5,6,7-hexahydroindolizine-8-carboxamide
  参考文献：
  名称：

  Formal Synthesis of (5R,8R,8aS)-Indolizidine 209I via Enaminones Incorporating Weinreb Amides

  摘要：

  A formal enantioselective synthesis of the amphibian alkaloid (5R,8R,8aS)-(-)-indolizidine 2091 (6) is reported. Control or the absolute, stereochemistry at C-5 resulted from application of the Davies procedure, which entails stereoselective conjugate addition of (R)-(+)-N-benzyl-1-phenylethylamine to tert-butyl (E)-hex-2-enoate. The resulting chiral adduct 26 was converted in eight steps into a pivotal enaminone incorporating a Weinreb amide, the inherent nucleophilicity of which was exploited in a cyclisation that yielded the key bicyclic intermediate (5R)-N-methoxy- N-methyl-5-propyl-1,2,3,5,6,7-hexahydroindolizine-8-carboxamide (38). Stereoselective catalytic hydrogenation of the alkene bond, reaction of the Weinreb amide with ethylmagnesium bromide, and epimerisation of the resulting ketone completed the formal synthesis of the target alkaloid.

  DOI：

  10.3987/com-08-s(d)68
• 作为产物：
  描述：

  3-[(2E)-2-{2-[methoxy(methyl)amino]-2-oxoethylidene}pyrrolidin-1-yl]propyl acetate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以83%的产率得到(2E)-2-[1-(3-hydroxypropyl)pyrrolidin-2-ylidene]-N-methoxy-N-methylethanamide
  参考文献：
  名称：

  Formal Synthesis of (5R,8R,8aS)-Indolizidine 209I via Enaminones Incorporating Weinreb Amides

  摘要：

  A formal enantioselective synthesis of the amphibian alkaloid (5R,8R,8aS)-(-)-indolizidine 2091 (6) is reported. Control or the absolute, stereochemistry at C-5 resulted from application of the Davies procedure, which entails stereoselective conjugate addition of (R)-(+)-N-benzyl-1-phenylethylamine to tert-butyl (E)-hex-2-enoate. The resulting chiral adduct 26 was converted in eight steps into a pivotal enaminone incorporating a Weinreb amide, the inherent nucleophilicity of which was exploited in a cyclisation that yielded the key bicyclic intermediate (5R)-N-methoxy- N-methyl-5-propyl-1,2,3,5,6,7-hexahydroindolizine-8-carboxamide (38). Stereoselective catalytic hydrogenation of the alkene bond, reaction of the Weinreb amide with ethylmagnesium bromide, and epimerisation of the resulting ketone completed the formal synthesis of the target alkaloid.

  DOI：

  10.3987/com-08-s(d)68

文献信息

• New syntheses of (±)-tashiromine and (±)-epitashiromine via enaminone intermediates
  作者：Darren L Riley、Joseph P Michael、Charles B de Koning

  DOI：10.3762/bjoc.12.256

  日期：——

  The syntheses of the naturally occurring indolizidine alkaloid (±)-tashiromine and its unnatural epimer (±)-epitashiromine are demonstrated through the use of enaminone chemistry. The impact of various electron-withdrawing substituents at the C-8 position of the indolizidine core on the preparation of the bicyclic system is described.

  通过使用烯胺酮化学方法，演示了天然存在的吲哚啉生物碱(±)-太白胺和其非自然对映体(±)-表太白胺的合成。描述了在吲哚啉核心的C-8位置引入不同电子吸引取代基对双环系统制备的影响。