(2S)-N-tritylpyrrolidine-2-carboxamide | 123987-23-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (2S)-N-tritylpyrrolidine-2-carboxamide
• 英文别名: (S)-N-tritylpyrrolidine-2-carboxamide
• CAS: 123987-23-5
• 化学式: C₂₄H₂₄N₂O
• 分子量: 356.467
• InChiKey: YSIFDMNGBQNXEM-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-N-tritylpyrrolidine-2-carboxamide 在 三乙胺 、 potassium iodide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 10.0h， 生成
  参考文献：
  名称：

  新型季胍盐基相转移催化剂对芳烃的催化对映选择性亲核加成

  摘要：

  由于芳炔的生成方法温和，在合成化学中得到了广泛的应用。然而，用芳烃实现不对称有机催化反应仍然是一个艰巨且罕见的挑战，主要是因为这些中性和瞬态物质往往会自发猝灭。为了解决这个问题，设计了一种固液相转移策略，其中芳炔的生成速度可以通过原位生成的氟化物基手性相转移催化剂来控制。在这项研究中，我们利用基于氨基酰胺的胍盐QG •X，提出了一种涉及芳烃的催化对映选择性亲核加成反应。此外，我们证明了该反应与各种芳烃和环状/无环β-酮酰胺的广泛相容性，从而产生具有良好立体选择性的多种α-芳基季立体中心。机理研究发现，在QG ·X 和 CsF 之间的离子交换过程中，手性分子内阳离子-阴离子对和 HF 可能参与亲核试剂活化和芳基生成。此外，DFT 计算表明，观察到的高水平对映选择性可归因于空间排斥以及催化剂和底物之间累积的非共价相互作用。

  DOI：

  10.1021/jacs.3c09594
• 作为产物：
  描述：

  benzyl (2S)-2-(tritylcarbamoyl)pyrrolidine-1-carboxylate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 生成 (2S)-N-tritylpyrrolidine-2-carboxamide
  参考文献：
  名称：

  Enantioselective Organocatalytic Biginelli Reaction: Dependence of the Catalyst on Sterics, Hydrogen Bonding, and Reinforced Chirality

  摘要：

  From a systematic investigation involving the synthesis of a series of catalysts and screening studies, the organocatalyst 16, which is sterically hindered, contains a strong hydrogen-bonding site, and is endowed with reinforced chirality, is shown to promote the Biginelli cyclocondensation of aromatic as well as aliphatic aldehydes with ethyl acetoacetate and urea in a remarkably high enantioselectivity (ee ca. 94-99%).

  DOI：

  10.1021/jo101717m
• 作为试剂：
  描述：

  正丁醛 、 1-(2-糠酰)-2-硝基乙烯 在 (2S)-N-tritylpyrrolidine-2-carboxamide 、 苯甲酸 作用下， 以 甲苯 为溶剂， 反应 24.5h， 以93%的产率得到
  参考文献：
  名称：

  Aromatic l-prolinamide-catalyzed asymmetric Michael addition of aldehydes to nitroalkenes

  摘要：

  Two chiral aromatic L-prolinamides were synthesized in high overall yield (95%) from N-Boc-L-proline and served as organocatalysts in asymmetric Michael reactions of aldehydes to nitroalkenes. Under the optimized reaction conditions, (S)-N-tritylpyrrolidine-2-carboxamide 4 was found to be a highly efficient organocatalyst for the Michael addition, and the corresponding Michael adducts were obtained in good yields (up to 94%), with excellent enantioselectivities (up to 99% ee) and diastereoselectivities (up to 99:1 dr). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.11.006

文献信息

• Organocatalytic asymmetric Michael reaction with acylsilane donors
  作者：Lei Wu、Guangxun Li、Qingquan Fu、Luoting Yu、Zhuo Tang

  DOI：10.1039/c2ob26950c

  日期：——

  We have developed an organocatalytic asymmetric Michael reaction of acylsilane through the selection of acylsilane substrates and organocatalysts, thus creating a rare example of acylsilane α-alkylation with a chiral guanidine catalyst, which afforded products in good yields and high stereoselectivity. The corresponding adducts described here have also been demonstrated to be useful in the synthesis

  通过选择酰基硅烷底物和有机催化剂，我们开发了酰基硅烷的有机催化不对称迈克尔反应，从而创造了一个罕见的手性胍催化剂进行酰基硅烷α-烷基化的例子，该产物能够提供高收率和高立体选择性。还已经证明，在此描述的相应的加合物可用于合成非天然氨基酸和生物活性化合物。
• Enantiometric iodobenzamides
  申请人：THE VANDERBILT UNIVERSITY

  公开号：EP0320630A1

  公开（公告）日：1989-06-21

  Novel iodine-substituted benzamide derivatives of formula I wherein R¹ is a hydrogen atom, a lower alkyl group consisting of 1 to 4 carbon atoms, a cycloalkyl group consisting of 3 to 7 carbon atoms, an alkenyl group consisting of 2 to 4 carbon atoms, an alkynyl group consisting of 2 to 4 carbon atoms, a phenyl group, a halogen substituted phenyl group, or an enantiomer or pharmaceutically suitable salt thereof, exhibit high blocking activity and specifity for the dopamine D-2 receptor.

  式I的新碘取代苯甲酰胺衍生物，其中R¹是氢原子，由1至4个碳原子组成的较低烷基基团，由3至7个碳原子组成的环烷基基团，由2至4个碳原子组成的烯基基团，由2至4个碳原子组成的炔基基团，苯基，卤素取代的苯基，或其对映体或药学上适用的盐，表现出对多巴胺D-2受体的高阻断活性和特异性。
• First example of an organocatalytic asymmetric Mannich reaction between aldimines of glycinates and sulphonyl imines
  作者：Lei Wu、Guangxun Li、Migu He、Yingwei Wang、Gang Zhao、Zhuo Tang

  DOI：10.1139/cjc-2016-0089

  日期：2016.9

  enantioselective Mannich-type reaction between glycinate Schiff base and imines has been one of the most efficient routes for accessing α,β-diamino acids. However, the glycinate Schiff bases used in the references were almost ketimines. Only several examples of aldimines were used in the presence of metal catalyst. We developed the first example of an asymmetric direct Mannich reaction using aldimines of glycinates

  甘氨酸席夫碱和亚胺之间的催化对映选择性曼尼希型反应是获取 α,β-二氨基酸的最有效途径之一。然而，参考文献中使用的甘氨酸席夫碱几乎是酮亚胺。在金属催化剂的存在下仅使用了几个醛亚胺的例子。我们开发了第一个使用甘氨酸醛亚胺代替甘氨酸酮亚胺进行不对称直接曼尼希反应的例子。该反应由手性胍很好地催化，具有高产率（高达 92%）和中等立体选择性（高达 65%）。
• Enantioselective Organocatalytic Biginelli Reaction: Dependence of the Catalyst on Sterics, Hydrogen Bonding, and Reinforced Chirality
  作者：Satyajit Saha、Jarugu Narasimha Moorthy

  DOI：10.1021/jo101717m

  日期：2011.1.21

  From a systematic investigation involving the synthesis of a series of catalysts and screening studies, the organocatalyst 16, which is sterically hindered, contains a strong hydrogen-bonding site, and is endowed with reinforced chirality, is shown to promote the Biginelli cyclocondensation of aromatic as well as aliphatic aldehydes with ethyl acetoacetate and urea in a remarkably high enantioselectivity (ee ca. 94-99%).
• Aromatic l-prolinamide-catalyzed asymmetric Michael addition of aldehydes to nitroalkenes
  作者：Yongchao Wang、Jun Lin、Kun Wei

  DOI：10.1016/j.tetasy.2014.11.006

  日期：2014.12

  Two chiral aromatic L-prolinamides were synthesized in high overall yield (95%) from N-Boc-L-proline and served as organocatalysts in asymmetric Michael reactions of aldehydes to nitroalkenes. Under the optimized reaction conditions, (S)-N-tritylpyrrolidine-2-carboxamide 4 was found to be a highly efficient organocatalyst for the Michael addition, and the corresponding Michael adducts were obtained in good yields (up to 94%), with excellent enantioselectivities (up to 99% ee) and diastereoselectivities (up to 99:1 dr). (C) 2014 Elsevier Ltd. All rights reserved.