tert-butyl (2S)-2-({2-[(4-methylbenzene)sulfonamido]ethyl}carbamoyl)pyrrolidine-1-carboxylate | 1372027-24-1

• 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: tert-butyl (2S)-2-({2-[(4-methylbenzene)sulfonamido]ethyl}carbamoyl)pyrrolidine-1-carboxylate
• 英文别名: tert-butyl (2S)-2-[2-[(4-methylphenyl)sulfonylamino]ethylcarbamoyl]pyrrolidine-1-carboxylate
• CAS: 1372027-24-1
• 化学式: C₁₉H₂₉N₃O₅S
• 分子量: 411.522
• InChiKey: OZHIIPNVWJUUKD-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S)-2-({2-[(4-methylbenzene)sulfonamido]ethyl}carbamoyl)pyrrolidine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以80%的产率得到(S)-N-(2-(4-methylphenylsulfonamido)ethyl)pyrrolidine-2-carboxamide
  参考文献：
  名称：

  Novel supported and unsupported prolinamides as organocatalysts for enantioselective cyclization of triketones

  摘要：

  A novel prolylsulfonamide derived from ethylene diamine and its supported counterpart has been prepared and tested as enantioselective intramolecular aldol reaction of cyclic and acyclic triketones. Good to excellent yields and enantioselectivities have been obtained in water and under solvent free conditions. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.123
• 作为产物：
  描述：

  对甲苯磺酰氯 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 10.75h， 生成 tert-butyl (2S)-2-({2-[(4-methylbenzene)sulfonamido]ethyl}carbamoyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Novel supported and unsupported prolinamides as organocatalysts for enantioselective cyclization of triketones

  摘要：

  A novel prolylsulfonamide derived from ethylene diamine and its supported counterpart has been prepared and tested as enantioselective intramolecular aldol reaction of cyclic and acyclic triketones. Good to excellent yields and enantioselectivities have been obtained in water and under solvent free conditions. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.123

文献信息

• New Binaphthyl-Proline-Based Chiral Ligands Bearing Imidazoline Groups: Design, Synthesis, and Their Application in Enantioselective Conjugate Addition of 4-Hydroxycoumarin and Related Nucleophiles to β,γ-Unsaturated α-Ketoesters
  作者：Shibo Yu、Qihang Cai、Tianxu Yu、Jiahui Li、Chao Yao、Yue-Ming Li

  DOI：10.1021/acs.joc.3c01262

  日期：2023.11.3

  This paper describes the design and application of new binaphthyl-proline-based chiral ligands bearing imidazoline functional groups. These chiral ligands incorporate the advantages of both the binaphthyl and proline skeletons, they are featured with regulatable electronic and steric properties for the imidazoline functional groups, and form chiral complexes with different metal salts such as cuprous

  本文介绍了带有咪唑啉官能团的新型联萘脯氨酸手性配体的设计和应用。这些手性配体结合了联萘和脯氨酸骨架的优点，具有可调节咪唑啉官能团的电子和空间性质，并与不同的金属盐（例如乙酸亚铜）形成手性配合物。在适量的手性催化剂存在下，4-羟基香豆素或相关亲核试剂与不同的β,γ-不饱和α-酮酯的对映选择性共轭加成反应很容易进行，得到了高产率（高达99%）和优异的所需产物。对映体过量（高达 99%）。
• Novel supported and unsupported prolinamides as organocatalysts for enantioselective cyclization of triketones
  作者：Rafael Pedrosa、José María Andrés、Rubén Manzano、César Pérez-López

  DOI：10.1016/j.tetlet.2013.03.123

  日期：2013.6

  A novel prolylsulfonamide derived from ethylene diamine and its supported counterpart has been prepared and tested as enantioselective intramolecular aldol reaction of cyclic and acyclic triketones. Good to excellent yields and enantioselectivities have been obtained in water and under solvent free conditions. (C) 2013 Elsevier Ltd. All rights reserved.