3-苯基-3-(吡咯烷-1-基)丙酸甲酯 | 7032-65-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 3-苯基-3-(吡咯烷-1-基)丙酸甲酯
• 英文名称: methyl 3-phenyl-3-pyrrolidinylpropionate
• 英文别名: 3-phenyl-3-pyrrolidin-1-yl-propionic acid methyl ester；β-Pyrrolidino-hydroxyzimtsaeure-methylester；3-Pyrrolidino-3-phenyl-propionsaeure-methylester；Methyl 3-phenyl-3-(pyrrolidin-1-YL)propanoate；methyl 3-phenyl-3-pyrrolidin-1-ylpropanoate
• CAS: 7032-65-7
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: OSVHNYZORQSSKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  四氢吡咯 、 Methyl cinnamate 在 lithium perchlorate 作用下， 反应 2.0h， 以80%的产率得到3-苯基-3-(吡咯烷-1-基)丙酸甲酯
  参考文献：
  名称：

  LiClO4 Accelerated Michael addition of amines to α,β-unsaturated olefins under solvent-free conditions

  摘要：

  Several primary and secondary amines were added to alpha,beta-unsaturated esters, nitriles, amides, and ketones to give the corresponding saturated amines mediated by solid lithium perchlorate under solvent-free and environmentally friendly conditions at room temperature. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.11.012

文献信息

• B(OMe)₃as a Nonacidic Iminium Ion Generator in Mannich- and Ugi-Type Reactions
  作者：Yusuke Tanaka、Kousuke Hidaka、Tomoaki Hasui、Michinori Suginome

  DOI：10.1002/ejoc.200801190

  日期：2009.3

  Mannich-type reactions of aldehydes with secondary amines and a ketene silyl acetal were promoted by trimethoxyborane in DMSO to afford the corresponding β-amino esters in good yields. B(OMe)3 also promoted Ugi-type reactions ofaldehydes with secondary amines and isocyanides in 1,2-dichloroethane, which leads to the formation of α-amino amides. In these reactions, trimethoxyborane serves as an inexpensive

  三甲氧基硼烷在 DMSO 中促进醛与仲胺和乙烯酮甲硅烷基缩醛的曼尼希型反应，以良好的产率得到相应的 β-氨基酯。B(OMe)3 还促进醛与仲胺和异氰化物在 1,2-二氯乙烷中的 Ugi 型反应，从而形成 α-氨基酰胺。在这些反应中，三甲氧基硼烷用作廉价、市售且几乎非酸性的亚胺离子发生器。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Diarylborinic Acid Derivatives as a Catalytic Iminium Ion Generator in the Mannich-Type Reaction Using Secondary Amines, Aldehydes, and Ketene Silyl Acetals
  作者：Michinori Suginome、Yusuke Tanaka、Tomoaki Hasui

  DOI：10.1055/s-2008-1072724

  日期：2008.5

  Reactions of secondary amines, aldehydes, and ketene silyl acetals were efficiently promoted by catalytic amounts of diarylborinic acid esters, Ar 2 B(OR), affording β-amino esters selectively with no formation of the corresponding β-hydroxy esters.

  催化量的二芳基硼酸酯 Ar 2 B(OR) 有效地促进了仲胺、醛和乙烯酮甲硅烷基缩醛的反应，选择性地提供了 β-氨基酯，而不会形成相应的 β-羟基酯。
• Bromodimethylsulfonium bromide mediated Michael addition of amines to electron deficient alkenes
  作者：Abu T. Khan、Tasneem Parvin、Sarifuddin Gazi、Lokman H. Choudhury

  DOI：10.1016/j.tetlet.2007.03.163

  日期：2007.5

  Bromodimethylsulfonium bromide has been found to be an efficient catalyst for the Michael addition of a wide variety of amines to electron deficient alkenes at room temperature. The protocol is very simple and chemoselective. Aliphatic and benzylic amines undergo conjugate addition within a very short period under solvent-free conditions and provide excellent yields of products. (C) 2007 Published by Elsevier Ltd.
• Aminoboranes as “Compatible” Iminium Ion Generators in Aminative C−C Bond Formations
  作者：Michinori Suginome、Lars Uehlin、Masahiro Murakami

  DOI：10.1021/ja045827y

  日期：2004.10.1

  Aminoboranes have been shown to be highly efficient and mild iminium ion generators in the Mannich-type aminative coupling of aldehydes with silyl ketene acetals. By using aminoboranes bearing bulky amino groups, such as a diisopropylamino group, free secondary amines can be successfully used as the amino component in a three-component Mannich reaction with aldehydes and silyl ketene acetals.
• Aminoalkylation with Aldehydes Mediated by Solid Lithium Perchlorate
  作者：Mohammad R. Saidi、Mohammad Nazari

  DOI：10.1007/s00706-003-0093-2

  日期：2004.3.1

  The solid LiClO4-mediated one-pot reaction of aldehydes with secondary amines and C nucleophiles afforded the corresponding aminoalkylation products in high yields. Unlike the previous reported procedure, the aminoalkylation of aldehyde was achieved in the presence of only 0.5 equivalents of solid lithium perchlorate in dichloromethane as the solvent with good to high yields at room temperature.