(R)-pyrrolidine-2-carboxylic acid phenylamide | 104261-87-2

• 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: (R)-pyrrolidine-2-carboxylic acid phenylamide
• 英文别名: (R)-2-phenylaminocarbonylpyrrolidine；(R)-N-phenylpyrrolidine-2-carboxamide；N-phenylpyrrolidine-2-carboxamide；R-proline anilide；D-Proline anilide；(2R)-N-phenylpyrrolidine-2-carboxamide
• CAS: 104261-87-2
• 化学式: C₁₁H₁₄N₂O
• 分子量: 190.245
• InChiKey: NRXYBKZDRCXDOD-SNVBAGLBSA-N

物化性质

• 熔点：
  74-77 °C
• 沸点：
  399.3±35.0 °C(Predicted)
• 密度：
  1.164±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  (R)-pyrrolidine-2-carboxylic acid phenylamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以63%的产率得到(R)-(-)-2-(苯氨基甲基)吡咯烷
  参考文献：
  名称：

  Sulfonyl isatin compounds and methods of blocking apoptosis therewith

  摘要：

  本发明涉及一种新型的Formula (I)的磺酰异喹啉化合物，它们的药物组合物，以及用于治疗细胞凋亡和由过度或不适当的细胞死亡引起的疾病状态的新型caspase抑制剂。

  公开号：

  US06403792B1
• 作为产物：
  描述：

  tert-butyl (R)-2-(phenylcarbamoyl)pyrrolidine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (R)-pyrrolidine-2-carboxylic acid phenylamide
  参考文献：
  名称：

  具有α-氨基酸亚基的新型二酰胺衍生物的设计、合成和杀虫活性

  摘要：

  设计并合成了一系列含有α-氨基酸的二酰胺衍生物。评估了这些化合物对小菜蛾、单独的 Mythimna、桃蚜和红叶螨的杀虫活性。大多数含有l-苯基甘氨酸骨架的标题化合物在500 mg·L -1的浓度下具有良好的活性。化合物( R)-A6显示出作为杀虫先导物的进一步优化的潜在价值，LC 50值为86.8 mg·L -1。

  DOI：

  10.1002/jhet.4268
• 作为试剂：
  描述：

  对硝基苯甲醛 、 丙酮 在 (R)-pyrrolidine-2-carboxylic acid phenylamide 作用下， 以 水 为溶剂， 反应 72.0h， 生成 (4R)-4-hydroxy-4-(4-nitrophenyl)-butan-2-one 、 (4S)-4-hydroxy-4-(4-nitrophenyl)-butan-2-one
  参考文献：
  名称：

  Enantiopure Peptide-Functionalized Metal–Organic Frameworks

  摘要：

  We present herein the first example of metal-organic frameworks postfunctionalized with peptides. Our microwave-assisted postsynthetic modification method yields enantiopure peptides anchored inside MOF cavities. Al-MIL-101-NH2, In-MIL-68-NH2, and Zr-UiO-66-NH2 were chosen as starting platforms. A single amino acid and various oligopeptides are grafted with yields up to 60% after a 30 min microwave-assisted coupling-deprotection sequence. This allows efficient preparation of a library of functional hybrid solids for molecular recognition applications such as sensing, separation, or asymmetric catalysis, as demonstrated here for the chiral aldol reaction.

  DOI：

  10.1021/jacs.5b05327

文献信息

• Dynamic Thermodynamic and Dynamic Kinetic Resolution of 2-Lithiopyrrolidines
  作者：Iain Coldham、Samuel Dufour、Thomas F. N. Haxell、Jignesh J. Patel、Graciela Sanchez-Jimenez

  DOI：10.1021/ja061963m

  日期：2006.8.1

  for the dynamic resolution. Electrophilic quench of the resolved diastereomeric 2-lithiopyrrolidine-chiral ligand complexes provided the enantiomerically enriched 2-substituted pyrrolidines. With N-alkyl derivatives, the resolution occurs conveniently at (or just below) room temperature and either enantiomer of the product can be formed by appropriate choice of the chiral ligand. The asymmetric induction

  动态拆分已被研究作为一种不对称合成 2-取代吡咯烷的方法。已经实现了在手性配体存在下外消旋 2-硫代吡咯烷的高度对映选择性亲电取代。有机锂化合物是通过相应的三丁基锡烷和正丁基锂的锡-锂交换或通过 N-（叔丁氧羰基）吡咯烷与仲丁基锂的去质子化来制备的。为动态分辨率研究了一系列 N 取代基和手性配体。解析的非对映体 2-硫代吡咯烷-手性配体配合物的亲电猝灭提供了对映体富集的 2-取代吡咯烷。与 N-烷基衍生物，the resolution occurs conveniently at (or just below) room temperature and either enantiomer of the product can be formed by appropriate choice of the chiral ligand. 不对称诱导的发生是由于对一种非对映体复合物的热力学偏好。发
• CATALYST FOR ASYMMETRIC HYDROGENATION AND METHOD FOR MANUFACTURING OPTICALLY ACTIVE CARBONYL COMPOUND USING THE SAME
  申请人：YAMADA Shinya

  公开号：US20120136176A1

  公开（公告）日：2012-05-31

  The present invention provides a catalyst used for manufacturing an optically active carbonyl compound by selective asymmetric hydrogenation of an α,β-unsaturated carbonyl compound, which is insoluble in a reaction mixture, and a method for manufacturing the corresponding optically active carbonyl compound. Particularly, the invention provides a catalyst for obtaining an optically active citronellal useful as a flavor or fragrance, by selective asymmetric hydrogenation of citral, geranial or neral. The invention relates to a catalyst for asymmetric hydrogenation of an α,β-unsaturated carbonyl compound, which comprises: a powder of at least one metal selected from metals belonging to Group 8 to Group 10 of the Periodic Table, or a metal-supported substance in which the at least one metal is supported on a support; an optically active peptide compound; and an acid, and also relates to a method for manufacturing an optically active carbonyl compound using the same.

  本发明提供了一种用于通过选择性不对称加氢α，β-不饱和羰基化合物制备光学活性羰基化合物的催化剂，该催化剂在反应混合物中不溶解，并提供了制备相应光学活性羰基化合物的方法。特别地，该发明提供了一种催化剂，通过选择性不对称加氢柠檬醛、香叶醛或柠檬醛制备出用作香料或芳香剂的光学活性香茅醛。该发明涉及一种用于不对称加氢α，β-不饱和羰基化合物的催化剂，包括：来自周期表第8至第10族金属中至少一种金属的粉末，或者至少一种金属负载物质，其中至少一种金属负载在一种载体上；一种光学活性肽化合物；和一种酸，还涉及使用该催化剂制备光学活性羰基化合物的方法。
• CATALYST FOR ASYMMETRIC HYDROGENATION
  申请人：MAEDA Hironori

  公开号：US20100324338A1

  公开（公告）日：2010-12-23

  This invention aims at providing a catalyst for producing an optically active aldehyde or an optically active ketone, which is an optically active carbonyl compound, by carrying out selective asymmetric hydrogenation of an α,β-unsaturated carbonyl compound, particularly a catalyst which is insoluble in a reaction mixture for obtaining optically active citronellal which is useful as a flavor or fragrance, by carrying out selective asymmetric hydrogenation of citral, geranial or neral; and a method for producing a corresponding optically active carbonyl compound. The invention relates to a catalyst for asymmetric hydrogenation of an α,β-unsaturated carbonyl compound, which comprises a powder of at least one metal selected from metals belonging to Group 8 to Group 10 of the Periodic Table, or a metal-supported substance in which at least one metal selected from metals belonging to Group 8 to Group 10 of the Periodic Table is supported on a support, an optically active cyclic nitrogen-containing compound and an acid.

  这项发明旨在通过对α，β-不饱和羰基化合物进行选择性不对称加氢，特别是通过对柠檬醛、香叶醛或柠檬醛进行选择性不对称加氢，从而提供用作香料或香精的有用的光学活性香茅醛的催化剂，该香茅醛是一种光学活性羰基化合物；以及生产相应的光学活性羰基化合物的方法。该发明涉及一种用于不对称加氢α，β-不饱和羰基化合物的催化剂，其包括来自周期表第8至第10族金属中至少一种金属的粉末，或者至少一种来自周期表第8至第10族金属的金属负载物质，该金属负载在一种支撑物上，还包括光学活性的含氮环化合物和酸。
• Process for the preparation of an indoline carboxylic acid
  申请人：Ciba-Geigy Corporation

  公开号：US04595766A1

  公开（公告）日：1986-06-17

  The invention relates to a novel process for the preparation of the optically pure 2S- or 2R-indolinecarboxylic acid of the formula ##STR1## and salts thereof. The process comprises forming the heterocyclic 5-membered ring in formula I from an open chain precursor by diastereoselective cyclization.

  该发明涉及一种用于制备式中的光学纯2S-或2R-吲哚甲酸及其盐的新工艺。该工艺包括通过对映选择性环化将式中的杂环5-成员环从开链前体中形成。
• Catalyst for asymmetric hydrogenation and method for manufacturing optically active carbonyl compound using the same
  申请人：Yamada Shinya

  公开号：US08674144B2

  公开（公告）日：2014-03-18

  The present invention provides a catalyst used for manufacturing an optically active carbonyl compound by selective asymmetric hydrogenation of an α,β-unsaturated carbonyl compound, which is insoluble in a reaction mixture, and a method for manufacturing the corresponding optically active carbonyl compound. Particularly, the invention provides a catalyst for obtaining an optically active citronellal useful as a flavor or fragrance, by selective asymmetric hydrogenation of citral, geranial or neral. The invention relates to a catalyst for asymmetric hydrogenation of an α,β-unsaturated carbonyl compound, which comprises: a powder of at least one metal selected from metals belonging to Group 8 to Group 10 of the Periodic Table, or a metal-supported substance in which the at least one metal is supported on a support; an optically active peptide compound; and an acid, and also relates to a method for manufacturing an optically active carbonyl compound using the same.

  本发明提供了一种催化剂，用于通过选择性不对称氢化α，β-不饱和羰基化合物制造光学活性羰基化合物，该催化剂在反应混合物中不溶，以及制造相应的光学活性羰基化合物的方法。特别地，本发明提供了一种催化剂，通过选择性不对称氢化柠檬醛、香叶醛或柠檬醛萜烯，可获得一种用作香料或芳香剂的光学活性香茅醛。本发明涉及一种不对称氢化α，β-不饱和羰基化合物的催化剂，包括：来自周期表第8至第10组金属的至少一种金属的粉末，或者至少一种金属被支持在支持体上的金属支持物质；光学活性肽化合物；和酸，并且涉及使用该催化剂制造光学活性羰基化合物的方法。