(7S,7aS)-7-Methyl-hexahydro-pyrrolizin-3-one | 134527-81-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯里西啶类
• 英文名称: (7S,7aS)-7-Methyl-hexahydro-pyrrolizin-3-one
• 英文别名: (7S,8S)-7-methyl-1,2,5,6,7,8-hexahydropyrrolizin-3-one
• CAS: 134527-81-4
• 化学式: C₈H₁₃NO
• 分子量: 139.197
• InChiKey: XQRIFSFMAVSCKK-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (7S,7aS)-7-Methyl-hexahydro-pyrrolizin-3-one 以84%的产率得到
  参考文献：
  名称：

  Keusenkothen Paul F., Smith Michael B., J. Chem. Soc. Perkin Trans. 1, (1994) N 17, S 2485-2492

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-1-iodoethyl-5-vinylpyrrolidin-2-one 以87%的产率得到
  参考文献：
  名称：

  Keusenkothen Paul F., Smith Michael B., J. Chem. Soc. Perkin Trans. 1, (1994) N 17, S 2485-2492

  摘要：

  DOI：

文献信息

• Enantioselective total syntheses of indolizidine alkaloids (-)-205A and (-)-235B
  作者：Richard P. Polniaszek、Stephen E. Belmont

  DOI：10.1021/jo00016a013

  日期：1991.8

  Enantioselective total syntheses of indolizidine alkaloids (-)-205A and (-)-235B are described. The syntheses proceed via a common late-stage intermediate, alpha-aminonitrile 1. Absolute stereochemical control over the C8 and C8a stereocenters in these materials was achieved by a stereoselective crotylation reaction between chiral acyliminium ion (R)-3b and crotylmagnesium chloride. The selectivity of this reaction, which produced the (future)-8R,8aS configuration was complementary to the result obtained by crotylation of acyliminium ion (S)-3a with trans-crotyltrimethylsilane, which produced predominantly an adduct with the (future)-8S,8aS configuration. This latter crotyl lactam was converted to two additional diastereomers of alkaloid 205A. Comparison of the H-1 and C-13 NMR and optical rotation values of the four synthetic diastereomers of 205A with literature values supported the proposed assignment of the absolute and relative configuration of (-)-205A. The C-13 spectrum of synthetic (5R,8R,8aS)-235B was identical with that of natural 235B and supported the proposed assignment of relative configuration of the alkaloid. The optical rotation differed in sign and magnitude from the published value. Revised values of the optical rotations of (-)-205A and (-)-235B are suggested. This work constitutes the first enantioselective syntheses of 205A and 235B, which were prepared in 15 and 14 steps, respectively, from succinic anhydride, in an average overall yield of 17%.
• Keusenkothen Paul F., Smith Michael B., J. Chem. Soc. Perkin Trans. 1, (1994) N 17, S 2485-2492
  作者：Keusenkothen Paul F., Smith Michael B.

  DOI：——

  日期：——