benzyl-(2R)-2-(2’-oxopropyl) pyrrolidine-1-carboxylate | 1346132-33-9

• 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: benzyl-(2R)-2-(2’-oxopropyl) pyrrolidine-1-carboxylate
• 英文别名: benzyl 2-(2-oxopropyl)pyrrolidine-1-carboxylate；(R)-N-benzyloxycarbonyl-2-(2-oxopropyl)pyrrolidine；benzyl (2R)-2-(2-oxopropyl)pyrrolidine-1-carboxylate
• CAS: 1346132-33-9
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: QCQVDRPJQCXUMK-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl-(2R)-2-(2’-oxopropyl) pyrrolidine-1-carboxylate 在 lithium aluminium tetrahydride 、 硼烷四氢呋喃络合物 、 (S)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 (2S,2'R)-1-[N(1')-methylpyrrolidin-2'-yl]propan-2-ol
  参考文献：
  名称：

  An enantioselective synthesis of (+)-hygroline and (+)-pseudohygroline via Keck allylation and CBS reduction

  摘要：

  An enantioselective synthesis of (+)-hygroline and (+)-pseudohygroline has been achieved in high optical purity (98% ee) from readily available 1,4-butanediol. The synthesis strategy employs a Keck allylation, CBS reduction, and Wacker oxidation. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.06.012
• 作为产物：
  描述：

  戊-4-烯-1-基氨基甲酸苄酯 在 Hoveyda-Grubbs catalyst second generation 、 磷酸二苯酯 、 奎宁胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 58.0h， 生成 benzyl-(2R)-2-(2’-oxopropyl) pyrrolidine-1-carboxylate
  参考文献：
  名称：

  奎宁衍生的伯胺介导的不对称催化的分子内氮杂-迈克尔反应

  摘要：

  摘要建立了氨基甲酸酯，磺酰胺和乙酰胺对α，β-不饱和酮的分子内有机催化对映选择性氮杂-迈克尔反应。9-氨基-9-脱氧-表奎宁和磷酸二苯酯促进了该过程，从而快速，快速地合成了几种合成有用的五元和六元杂环，具有出色的对映选择性（92％–97.5％ee），并且良率极高（高达99％）。

  DOI：

  10.1016/j.cclet.2017.04.017

文献信息

• Asymmetric Organocatalytic Intramolecular Aza-Michael Addition of Enone Carbamates: Catalytic Enantioselective Access to Functionalized 2-Substituted Piperidines
  作者：Jian-Dong Liu、Ying-Chun Chen、Guo-Biao Zhang、Zhi-Qiang Li、Peng Chen、Ji-Yuan Du、Yong-Qiang Tu、Chun-An Fan

  DOI：10.1002/adsc.201100282

  日期：2011.10

  an achiral Brønsted acid, mostly proceeded in high yield and good to excellent stereocontrol (up to 99% ee). This reaction provides an alternative catalytic asymmetric method for installing the stereogenic nitrogen-containing carbon center in functionalized 2-substituted piperidines, leading to the development of a straightforward and expeditious synthesis of some naturally occurring bioactive 2-substituted

  通过烯酮氨基甲酸酯的有机催化对映选择性分子内氮杂-迈克尔加成反应已战略性地获得了具有侧酮基的合成有用的功能化2-取代的哌啶，其中烯酮部分作为迈克尔受体和氨基甲酸酯部分作为迈克尔的新型内部底物组合供体在不对称双功能有机催化中被发现。这种杂原子共轭加成反应是通过使用基于手性金鸡纳的手性叔叔二胺和非手性布朗斯台德酸实现的，主要以高收率和良好至优异的立体控制进行（最高ee为99％））。该反应提供了另一种催化不对称方法，用于在功能化的2-取代的哌啶中安装立体异构的含氮碳中心，从而导致了一些天然存在的生物活性的2-取代的哌啶生物碱的直接，快速合成的发展。
• Enantioselective synthesis of 2-substituted pyrrolidinesvia domino cross metathesis/intramolecular aza-Michael addition
  作者：Hanbin Liu、Chuanqi Zeng、Jiajia Guo、Mengyao Zhang、Shouyun Yu

  DOI：10.1039/c2ra22374k

  日期：——

  intramolecular aza-Michael addition with enone carbamates catalyzed by chiral Brønsted acids was developed. A domino cross metathesis/aza-Michael addition for the preparation of 2-substituted pyrrolidines or benzopyrrolidines was also explored. The reactions described here provide an efficient asymmetric protocol for enantio-enriched heterocycles, especially 2-substituted pyrrolidines.

  开发了一种高度对映选择性的分子内氮杂-迈克尔加成化合物，该化合物具有手性布朗斯台德酸催化的烯酮氨基甲酸酯。还研究了用于制备2-取代的吡咯烷或苯并吡咯烷的多米诺交叉复分解/氮杂-迈克尔加成反应。本文所述的反应为富含对映体的杂环，尤其是2-取代的吡咯烷酮提供了有效的不对称方案。
• Microwave-Assisted Organocatalytic Enantioselective Intramolecular aza-Michael Reaction with α,β-Unsaturated Ketones
  作者：Santos Fustero、Carlos del Pozo、Cristina Mulet、Rubén Lazaro、María Sánchez-Roselló

  DOI：10.1002/chem.201101292

  日期：2011.12.9

  AbstractAn organocatalytic enantioselective intramolecular aza‐Michael reaction of carbamates bearing conjugated ketones as Michael acceptors is described. By using 9‐amino‐9‐deoxy‐epi‐hydroquinine as the catalyst and pentafluoropropionic acid as a co‐catalyst, a series of piperidines, pyrrolidines, and the corresponding benzo‐fused derivatives (indolines, isoindolines, tetrahydroquinolines, and tetrahydroisoquinolines) can be obtained in excellent yields and enantioselectivities. In addition, the use of microwave irradiation at 60 °C improves the efficiency of the process giving rise to the final products with comparable yields and enantiomeric excesses. Some mechanistic insights are also considered.
• An enantioselective synthesis of (+)-hygroline and (+)-pseudohygroline via Keck allylation and CBS reduction
  作者：Shubhangi P. Bhoite、Rohit B. Kamble、Gurunath M. Suryavanshi

  DOI：10.1016/j.tetlet.2015.06.012

  日期：2015.8

  An enantioselective synthesis of (+)-hygroline and (+)-pseudohygroline has been achieved in high optical purity (98% ee) from readily available 1,4-butanediol. The synthesis strategy employs a Keck allylation, CBS reduction, and Wacker oxidation. (C) 2015 Elsevier Ltd. All rights reserved.
• Asymmetric catalyzed intramolecular aza-Michael reaction mediated by quinine-derived primary amines
  作者：Xian-Dong Zhai、Zhong-Duo Yang、Zhi Luo、Hong-Tao Xu

  DOI：10.1016/j.cclet.2017.04.017

  日期：2017.8

  Abstract An intramolecular organocatalytic enantioselective aza-Michael reaction of carbamates, sulfonamides and acetamides to α,β-unsaturated ketones was developed. This process is promoted by 9-amino-9-deoxy-epi-quinine and diphenyl hydrogen phosphate to afford a straightforward and expeditious synthesis of several synthetically useful five- and six-membered heterocycles with excellent enantioselectivity

  摘要建立了氨基甲酸酯，磺酰胺和乙酰胺对α，β-不饱和酮的分子内有机催化对映选择性氮杂-迈克尔反应。9-氨基-9-脱氧-表奎宁和磷酸二苯酯促进了该过程，从而快速，快速地合成了几种合成有用的五元和六元杂环，具有出色的对映选择性（92％–97.5％ee），并且良率极高（高达99％）。