1-(3-phenyl-1-propenyl)pyrrolidine | 154140-72-4

• 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-(3-phenyl-1-propenyl)pyrrolidine
• 英文别名: (E)-1-pyrrolidino-3-phenyl-1-propene；(E)-1-(3-phenylprop-1-en-1-yl)pyrrolidine；(E)-1-(1-Pyrrolidino)-3-phenyl-1-propene；1-[(1E)-3-Phenyl-1-propen-1-yl]pyrrolidine；1-[(E)-3-phenylprop-1-enyl]pyrrolidine
• CAS: 154140-72-4
• 化学式: C₁₃H₁₇N
• 分子量: 187.285
• InChiKey: RTKZMANONOBORT-WUXMJOGZSA-N

物化性质

• 沸点：
  310.1±22.0 °C(Predicted)
• 密度：
  1.061±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(3-phenyl-1-propenyl)pyrrolidine 在 氢溴酸 、 potassium carbonate 作用下， 以 二氯甲烷 、 溶剂黄146 、 乙腈 为溶剂， 反应 71.0h， 生成 5-benzyl-4-methoxy-4-(trifluoromethyl)-3,4-dihydro-1H-pyrimidin-2-one
  参考文献：
  名称：

  Synthesis of some cyclic and acyclic nucleoside analogues derived from 4-(trifluoromethyl)pyrimidines

  摘要：

  Cyclic nucleoside analogues 10, 11, 13b-d and 17 and acyclic derivatives 19 and 20b-d were prepared from 4-trifluoromethyl-pyrimidones 4a and 5b-d. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00721-9
• 作为产物：
  描述：

  四氢吡咯 、 苯丙醛 在 potassium carbonate 作用下， 以 乙醚 为溶剂， 反应 12.0h， 以85%的产率得到1-(3-phenyl-1-propenyl)pyrrolidine
  参考文献：
  名称：

  烯胺的自由基还原烷基化的立体选择性：烯丙基1，3-应变模型的重要性

  摘要：

  据报道使用Bu 3 SnH作为还原剂向烯胺中自由基加成（方案2和4）。在不同系统中检查了这些反应的非对映选择性（表1和2）。衍生自环状酮（例如环己酮）的烯胺以高非对映选择性被烷基化，并优先形成顺式-二取代的环烷烃。在无环体系中，例如衍生自苯丙酮和二乙基酮的烯胺，在H提取步骤中观察到中等到高的立体选择性。主要基于最小化烯丙基1,3-应变（A 1,3 应变）是根据实验结果和半经验（AM1）计算得出的。

  DOI：

  10.1002/hlca.19930760707

文献信息

• Stereoselectivity of the Radical Reductive Alkylation of Enamines: Importance of the Allylic 1,3-Strain Model
  作者：Serge Schubert、Philippe Renaud、Pierre-Alain Carrupt、Kurt Schenk

  DOI：10.1002/hlca.19930760707

  日期：1993.11.3

  of the cis-disubstituted cycloalkanes. In acyclic systems such as enamines derived from propiophenone and diethyl ketone, moderate to high stereoselectivities were observed in the H-abstraction step. A model based principally on minimization of allylic 1,3-strain (A1,3 strain) was deduced from the experimental results and semi-empirical (AM1) calculations.

  据报道使用Bu 3 SnH作为还原剂向烯胺中自由基加成（方案2和4）。在不同系统中检查了这些反应的非对映选择性（表1和2）。衍生自环状酮（例如环己酮）的烯胺以高非对映选择性被烷基化，并优先形成顺式-二取代的环烷烃。在无环体系中，例如衍生自苯丙酮和二乙基酮的烯胺，在H提取步骤中观察到中等到高的立体选择性。主要基于最小化烯丙基1,3-应变（A 1,3 应变）是根据实验结果和半经验（AM1）计算得出的。
• Reactions of Conjugate Phosphinyl- and Phosphonyl-Nitroso Alkenes with Enamines. Preparation of <i>N</i>-Hydroxypyrrole Derivatives
  作者：Jesús M. de los Santos、Roberto Ignacio、Domitila Aparicio、Francisco Palacios、José M. Ezpeleta

  DOI：10.1021/jo900489j

  日期：2009.5.1

  The synthesis of highly functionalized N-hydroxypyrrole derivatives by the formal [3+2] cycloaddition reaction of enamines and nitroso alkenes derived from phosphine oxides and phosphonates is reported. Intermediate phosphorylated nitrones, whose formation can be explained by a conjugate addition of enamines to phosphorylated nitroso alkenes and formation of the five-membered heterocycles, are isolated

  报道了通过衍生自氧化膦和膦酸酯的烯胺和亚硝基烯烃的正式[3 + 2]环加成反应合成高度官能化的N-羟基吡咯衍生物。分离了中间体磷酸化的硝酮，其形成可以通过将烯胺共轭添加到磷酸化的亚硝基烯烃中和五元杂环的形成来解释。
• Igarashi, Mamoru; Tada, Masaru, Journal of Heterocyclic Chemistry, 1995, vol. 32, # 3, p. 807 - 810
  作者：Igarashi, Mamoru、Tada, Masaru

  DOI：——

  日期：——
• A Facile New Synthesis of Aldehyde Enamines in High Yield and High Purity
  作者：Gary B. Fisher、Lawrence Lee、Frederick W. Klettke

  DOI：10.1080/00397919408010154

  日期：1994.6

  Aldehyde enamines were synthesized in excellent yield and purity by reacting an aldehyde with 2 equivalents of a secondary amine in cyclohexane in the presence of 1.5 equivalents of CaH2. Distilled yields ranged from 65%-92%.
• Boranes in Synthesis. 5. The Hydroboration of Enamines with Mono- and Dialkylboranes. Asymmetric Synthesis of .beta.-Amino Alcohols of Moderate Enantiomeric Purity from Aldehyde Enamines
  作者：Gary B. Fisher、Christian T. Goralski、Lawrence W. Nicholson、Dennis L. Hasha、Donald Zakett、Bakthan Singaram

  DOI：10.1021/jo00112a026

  日期：1995.4

  The hydroboration of both acyclic and cyclic aldehyde and ketone enamines with such representative mono- and dialkylboranes as thexylborane and dicyclohexylborane, followed by an oxidative workup, yields the corresponding beta-amino alcohols in good to excellent isolated yields. The hydroboration of ketone and aldehyde enamines with the asymmetric hydroboration reagents monoisopinocampheylborane ((d)IpcBH(2)) and diisopinocampheylborane ((d)Ipc(2)BH) was also investigated, (d)Ipc(2)BH is highly effective for the asymmetric hydroboration of acyclic aldehyde enamines, such as 1-(4-morpholino)-3-phenyl-1-propene and 1-(1-pyrrolidino)-1-octene. Oxidation of the intermediate trialkylborane furnishes the corresponding beta-amino alcohols in 50-86% ee. The stereogenic center of the carbinol carbon is consistently enriched in the R-enantiomer when (d)Ipc(2)BH prepared from (+)-alpha-pinene is used as the hydroboration reagent. The enantiomeric excesses of the beta-amino alcohols synthesized in this study were determined by HPLC using a chiral stationary phase. The absolute configurations of some of the beta-amino alcohols synthesized in this study were determined by chiral HPLC comparison with authentic beta-amino alcohols prepared from chiral epoxides of known absolute configuration.