1-((1S)-1-phenylethyl)-5-(1-prop-2-enyl)-2-pyrrolidinone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-((1S)-1-phenylethyl)-5-(1-prop-2-enyl)-2-pyrrolidinone
• 英文别名: N-<(S)-1'-Phenylethyl>-5-prop-2''-enylpyrrolidin-2-one；5-allyl-1-[(S)-1-phenylethyl]pyrrolidin-2-one；1-[(1S)-1-phenylethyl]-5-prop-2-enylpyrrolidin-2-one
• 化学式: C₁₅H₁₉NO
• 分子量: 229.322
• InChiKey: BRJIDXSGXFPIAV-NBFOIZRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  1-((1S)-1-phenylethyl)-5-(1-prop-2-enyl)-2-pyrrolidinone 在 palladium on activated charcoal 盐酸 、 sodium tetrahydroborate 、 ammonium formate 、 lithium diisopropyl amide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 7.5h， 生成 (5R,8aR)-5-hexyloctahydroindolizine
  参考文献：
  名称：

  Enantioselective total syntheses of indolizidine alkaloids 167B and 209D

  摘要：

  DOI：

  10.1021/jo00302a038
• 作为产物：
  描述：

  5-hydroxy-1-[(1S)-1-phenylethyl]pyrrolidin-2-one 在 偶氮二异丁腈 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 19.0h， 生成 1-((1S)-1-phenylethyl)-5-(1-prop-2-enyl)-2-pyrrolidinone
  参考文献：
  名称：

  Asymmetric induction ? to nitrogen in pyrrolidines and piperidines via radical chemistry

  摘要：

  展示了对在氮上携带手性辅助基的吡咯烷和哌啶的2位自由基反应的立体化学控制的尝试。

  DOI：

  10.1039/p19960001107

文献信息

• N-Acyliminium Ion Chemistry: Improving the Access to Unsaturated γ-Lactams and Their N-α-Methoxylated Derivatives: Application to an Expeditive Synthesis of (±)-Crispine A
  作者：Joëlle Pérard-Viret、Florence Souquet、Wassila Drici、Sandra Abi Fayssal、Imane Lazouni、Sébastien Thueillon

  DOI：10.1055/s-0040-1707886

  日期：——

  Dedicated to Dr. Jacques Royer Abstract An improved synthesis of unsaturated γ-lactams by condensation of various primary amines with 2,5-dimethoxy-2,5-dihydrofuran is described. A modified mechanism for this reaction is suggested. Synthesis of their N-α-methoxylated derivatives, as N-acyliminium ion precursors, is also reported. Finally, a short synthesis of (±)-crispine A is presented as an illustrative

  献给雅克·罗耶（Jacques Royer）博士 抽象 描述了通过各种伯胺与2，5-二甲氧基-2，5-二氢呋喃缩合的改进的不饱和γ-内酰胺的合成。建议对该反应进行改进的机理。还报道了它们的N -α-甲氧基化衍生物，作为N-酰基亚胺离子前体的合成。最后，提出了（±）-crispine A的简短合成作为说明性应用。
• 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%.
• Stereoselective nucleophilic additions to the carbon-nitrogen double bond. 3. Chiral acyliminium ions
  作者：Richard P. Polniaszek、Stephen E. Belmont、Ramon Alvarez

  DOI：10.1021/jo00288a036

  日期：1990.1