tert-butyl (3R)-3-((2E)-2-{2-[methoxy(methyl)amino]-2-oxoethylidene}pyrrolidin-1-yl)hexanoate | 1162651-07-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: tert-butyl (3R)-3-((2E)-2-{2-[methoxy(methyl)amino]-2-oxoethylidene}pyrrolidin-1-yl)hexanoate
• CAS: 1162651-07-1
• 化学式: C₁₈H₃₂N₂O₄
• 分子量: 340.463
• InChiKey: LMXNLUBDSYNYKP-FQZGENGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  59.08
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (3R)-3-((2E)-2-{2-[methoxy(methyl)amino]-2-oxoethylidene}pyrrolidin-1-yl)hexanoate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 16.0h， 以11%的产率得到(2E)-2-{1-[(1R)-1-(2-hydroxyethyl)butyl]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
• 作为产物：
  描述：

  2-溴-N-甲氧基-N-甲基乙酰胺 、 tert-butyl (3R)-3-(2-thioxopyrrolidin-1-yl)hexanoate 在 三乙胺 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 19.0h， 以77%的产率得到tert-butyl (3R)-3-((2E)-2-{2-[methoxy(methyl)amino]-2-oxoethylidene}pyrrolidin-1-yl)hexanoate
  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