(S)-pyrrolidine-2-carboxylic acid (4-methylpyridin-2-yl)amide | 478912-53-7

• 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)-pyrrolidine-2-carboxylic acid (4-methylpyridin-2-yl)amide
• 英文别名: (2S)-N-(pyridin-2-yl)pyrrolidine-2-carboxamide；(2S)-N-(4-Methyl-2-pyridinyl)-2-pyrrolidinecarboxamide；(2S)-N-(4-methylpyridin-2-yl)pyrrolidine-2-carboxamide
• CAS: 478912-53-7
• 化学式: C₁₁H₁₅N₃O
• 分子量: 205.26
• InChiKey: TUENXGMNTWAZBG-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  54
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-pyrrolidine-2-carboxylic acid (4-methylpyridin-2-yl)amide 、 靛红 以 二氯甲烷 为溶剂， 反应 12.0h， 以87%的产率得到
  参考文献：
  名称：

  Highly stereoselective synthesis of novel spiroimidazolidinones directed by pyridine prolinamide

  摘要：

  A facile approach to the stereoselective synthesis of spiroimidazolidinones was described. A variety of novel polycyclic spiroimidazolidinones derived from isatin were prepared by employing easily available 2-pyridyl prolinamide as a chiral scaffold. Interestingly, the N-2-pyridyl motif played a vital role in improving the diastereoselectivity of this protocol. As a result, excellent diastereoselectivities (>20:1 dr) and good to excellent yields (60-96%) were achieved under extremely mild reaction conditions. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.12.055
• 作为产物：
  描述：

  N-苄氧羰基-L-脯氨酸 在 palladium on activated charcoal 氢气 、 氯甲酸乙酯 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.5h， 生成 (S)-pyrrolidine-2-carboxylic acid (4-methylpyridin-2-yl)amide
  参考文献：
  名称：

  Design of Highly Enantioselective Organocatalysts Based on Molecular Recognition

  摘要：

  Various organocatalysts have been designed based on molecular recognition to catalyze the asymmetric direct aldol reaction of ketones with aryl and alkyl alpha-keto acids, affording beta-hydroxyl carboxylic acids with a tertiary stereogenic center with excellent enantioselectivities of up to 98% ee. A linear effect was observed for the reaction, demonstrating a single molecule of the catalyst involved in the catalysis.

  DOI：

  10.1021/ol0529391

文献信息

• Asymmetric Organocatalytic Direct Aldol Reactions of Ketones with α-Keto Acids and Their Application to the Synthesis of 2-Hydroxy-γ-butyrolactones
  作者：Xiao-Ying Xu、Zhuo Tang、Yan-Zhao Wang、Shi-Wei Luo、Lin-Feng Cun、Liu-Zhu Gong

  DOI：10.1021/jo701868t

  日期：2007.12.1

  of organocatalysts for the asymmetric direct aldol reactions of ketones with α-keto acids were designed on the basis of molecular recognition and prepared from proline and aminopyridines. The organic molecule 8e, derived from proline and 6-methyl-2-amino pyridine, was the best catalyst, affording excellent enantioselectivities (up to 98% ee) for the direct aldol reactions of acetone or 2-butanone with

  在分子识别的基础上，设计了多种有机催化剂，用于酮与α-酮酸的不对称直接羟醛直接反应，并由脯氨酸和氨基吡啶制备。有机分子8e衍生自脯氨酸和6-甲基-2-氨基吡啶的最佳催化剂，对丙酮或2-丁酮与各种α-酮酸和用于各种无环脂族酮与3-（2-硝基苯基）-2-氧代丙酸的反应。通过非对映选择性还原和内酯化的反应序列可以将羟醛加成物转化为2-羟基-γ-丁内酯。对过渡态的实验和理论研究表明，有机催化剂的酰胺N和吡啶N分别与α-酮酸的酮氧基和羧酸羟基选择性地形成氢键。这两个氢键相互作用对于直接不对称羟醛缩合的反应性和对映选择性很重要。
• Highly stereoselective synthesis of novel spiroimidazolidinones directed by pyridine prolinamide
  作者：Jun-An Xiao、Chao-Ming Wang、Jing Wang、Guang-Chuan Ou、Xing-Yu Zhang、Hua Yang

  DOI：10.1016/j.tet.2014.12.055

  日期：2015.2

  A facile approach to the stereoselective synthesis of spiroimidazolidinones was described. A variety of novel polycyclic spiroimidazolidinones derived from isatin were prepared by employing easily available 2-pyridyl prolinamide as a chiral scaffold. Interestingly, the N-2-pyridyl motif played a vital role in improving the diastereoselectivity of this protocol. As a result, excellent diastereoselectivities (>20:1 dr) and good to excellent yields (60-96%) were achieved under extremely mild reaction conditions. (C) 2014 Elsevier Ltd. All rights reserved.
• Design of Highly Enantioselective Organocatalysts Based on Molecular Recognition
  作者：Zhuo Tang、Lin-Feng Cun、Xin Cui、Ai-Qiao Mi、Yao-Zhong Jiang、Liu-Zhu Gong

  DOI：10.1021/ol0529391

  日期：2006.3.1

  Various organocatalysts have been designed based on molecular recognition to catalyze the asymmetric direct aldol reaction of ketones with aryl and alkyl alpha-keto acids, affording beta-hydroxyl carboxylic acids with a tertiary stereogenic center with excellent enantioselectivities of up to 98% ee. A linear effect was observed for the reaction, demonstrating a single molecule of the catalyst involved in the catalysis.