(S)-tert-butyl 2-(quinolin-8-ylcarbamoyl)pyrrolidine-1-carboxylate | 955413-29-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-tert-butyl 2-(quinolin-8-ylcarbamoyl)pyrrolidine-1-carboxylate
• 英文别名: tert-butyl (2S)-2-[(quinolin-8-yl)carbamoyl]pyrrolidine-1-carboxylate；(S)-2-(quinolin-8-ylcarbamoyl)-pyrrolidine-1-carboxylic acid t-butyl ester；tert-butyl (2S)-2-(quinolin-8-ylcarbamoyl)pyrrolidine-1-carboxylate
• CAS: 955413-29-3
• 化学式: C₁₉H₂₃N₃O₃
• 分子量: 341.41
• InChiKey: LAFTTYHRTYEOPQ-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl 2-(quinolin-8-ylcarbamoyl)pyrrolidine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以695 mg的产率得到(S)-N-(quinolin-8-yl)pyrrolidine-2-carboxamide
  参考文献：
  名称：

  1-芳基-1-丙炔钯催化烯丙基烷基化反应中底物与配体的协同作用

  摘要：

  在烯胺-钯催化过程中，单保护氨基酸 Bz-Gly-OH 有助于各种酮、β-酮酯、醛等的烯丙基烷基化。密度泛函理论计算表明，Bz-Gly-OH 有助于形成烯胺，该烯胺通过外球机制攻击 π-烯丙基钯络合物。初步结果表明在双功能催化新模式下的不对称烯丙基烷基化。

  DOI：

  10.1021/acs.joc.2c00592
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 生成 (S)-tert-butyl 2-(quinolin-8-ylcarbamoyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  2'-羟基查耳酮对黄酮的对映选择性仿生环化

  摘要：

  已经开发了基于氨基喹啉和吡咯烷的新的有机催化剂家族，并显示其在模仿查尔酮环化的自然过程中催化2'-羟基查耳酮的直接和高度对映选择性环化。简单的合成过程在温和的反应条件下进行，可耐受水分和空气，对映体过量可达99％。这种方法为手性黄烷酮提供了一种简便而有效的途径。

  DOI：

  10.1016/j.tetlet.2014.04.032

文献信息

• Novel small molecules with selective cytotoxicity against human microvascular endothelial cell proliferation
  申请人：Kane L. John

  公开号：US20070254894A1

  公开（公告）日：2007-11-01

  Disclosed herein are angiogenesis inhibitors represented by formula (I) or formula (II): The variables for formulas (I) and (II) are defined herein.

  本文披露了由式(I)或式(II)表示的抑制血管生成的药物： 式(I)和式(II)中的变量在本文中有定义。
• Palladium-Catalyzed Directed C(sp³)-H Arylation of Saturated Heterocycles at C-3 Using a Concise Optimization Approach
  作者：Dominic P. Affron、James A. Bull

  DOI：10.1002/ejoc.201501300

  日期：2016.1

  Abstract Saturated heterocycles, such as THFs, pyrrolidines, piperidines and THPs, are essential components of many biologically active compounds. Examples of C–H functionalization on these important ring systems remain scarce, especially at unactivated positions. Here we report the development of conditions for the palladium‐catalyzed stereoselective C(sp3)–H arylation at unactivated 3‐positions of

  摘要 饱和杂环化合物，如THF、吡咯烷、哌啶和THP，是许多生物活性化合物的重要组成部分。这些重要环系统上的 C-H 官能化的例子仍然很少，特别是在未活化的位置。在这里，我们报道了钯催化的带有氨基喹啉导向基团的 5 元和 6 元 N 和 O 杂环的未活化 3 位上的立体选择性 C(sp3)-H 芳基化条件的开发。底物结构的细微差别显着改变了它们的反应性；在每种情况下，需要不同的条件才能获得高产量。使用简短的经验优化方法开发了成功的条件，以用一组有限的变量覆盖反应空间。在所有情况下都实现了优异的顺式选择性，除了 THP 底物，其中通过不同的环环中间体形成少量反式产物。在这里，检查了与其他指导基团的反应性和选择性的差异。
• Screening of simple N-aryl and N-heteroaryl pyrrolidine amide organocatalysts for the enantioselective aldol reaction of acetone with isatin
  作者：Michael Kinsella、Patrick G. Duggan、Claire M. Lennon

  DOI：10.1016/j.tetasy.2011.07.016

  日期：2011.7

  We have screened a range of simple N-aryl and N-heteroaryl pyrrolidine amide organocatalysts incorporating N-pyridyl and N-quinolinyl groups in the synthetically useful aldol reaction of isatin with acetone. The 'reverse amide' N-pyridyl pyrrolidinylmethyl amide catalysts proved highly catalytically active but gave disappointing enantioselectivities. However, an N-3-pyridyl prolinamide catalyst gave the aldol adduct in high yields and high enantioselectivity with up to 72% ee of the (S)-isomer. Conditions were optimised for this catalyst and in particular an additive screen identified a link between the pK(a) of the acid additive and the yield and enantioselectivity. An N-arylsulfonamide prolinamide was also identified as a catalyst for this reaction giving the (R)-enantiomer in 68% ee. (C) 2011 Elsevier Ltd. All rights reserved.
• Regio- and Stereospecific Synthesis of C-3 Functionalized Proline Derivatives by Palladium Catalyzed Directed C(sp³)–H Arylation
  作者：Dominic P. Affron、Owen A. Davis、James A. Bull

  DOI：10.1021/ol502511g

  日期：2014.9.19

  Functionalization of C(sp(3)) H bonds at the unactivated 3-position of proline derivatives has been achieved using aryl iodides and palladium catalysis. This directly affords cis-2,3-disubstituted pyrrolidines as single stereoisomers. 3-Arylation occurs in high yield under solvent-free conditions with aminoquinoline and methoxyaminoquinoline directing groups. The latter was readily removed to give primary amide derivatives with physicochemical properties appropriate for use as fragments in drug discovery.
• A novel trifunctional organocatalyst for the asymmetric aldol reaction: a facile enantioselective synthesis of β-hydroxyketones
  作者：B.V. Subba Reddy、K. Bhavani、A. Raju、J.S. Yadav

  DOI：10.1016/j.tetasy.2011.05.001

  日期：2011.4

  A new L-prolinamide trifunctional catalyst has been developed for the enantioselective aldol reaction of various aromatic and aliphatic aldehydes with acetone. This method provides high yields of beta-hydroxyketones (up to 90%) with good enantioselectivity (up to 92%) at a low catalyst loading (10 mol %). (C) 2011 Elsevier Ltd. All rights reserved.