benzyl (S)-2-(pyridin-3-ylcarbamoyl)pyrrolidine-1-carboxylate | 149521-97-1

• 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: benzyl (S)-2-(pyridin-3-ylcarbamoyl)pyrrolidine-1-carboxylate
• 英文别名: benzyl (2S)-2-(pyridin-3-ylcarbamoyl)pyrrolidine-1-carboxylate
• CAS: 149521-97-1
• 化学式: C₁₈H₁₉N₃O₃
• 分子量: 325.367
• InChiKey: IRBIKMATJVKSON-INIZCTEOSA-N

物化性质

• 沸点：
  559.1±50.0 °C(Predicted)
• 密度：
  1.301±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 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：

  benzyl (S)-2-(pyridin-3-ylcarbamoyl)pyrrolidine-1-carboxylate 在 氢溴酸 、 溶剂黄146 作用下， 反应 3.0h， 生成 (S)-2-(pyridinium-3'-ylcarbamoyl)pyrrolidinium dibromide
  参考文献：
  名称：

  Small organic molecule catalyzed enantioselective direct aldol reaction in water

  摘要：

  Protonated pyrrolidine based small organic molecules have been designed and evaluated for the asymmetric direct aldol reaction in water. The designed organocatalysts are multifunctional in nature and exploit the combined effect of hydrogen bonding and hydrophobic interactions for enantioselective catalysis in water. As a result a unique direct asymmetric aldol reaction in water catalyzed by a small organic molecule having an amide linkage has been developed. The developed catalyst affords chiral beta-hydroxyketones in good yields (93%) and enantioselectivities (upto 62%) in water. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.07.016
• 作为产物：
  描述：

  3-氨基吡啶 、 N-苄氧羰基-L-脯氨酸 在 氯甲酸乙酯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 benzyl (S)-2-(pyridin-3-ylcarbamoyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  酮与α-酮酸的不对称有机催化直接羟醛反应及其在2-羟基-γ-丁内酯合成中的应用

  摘要：

  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。

  DOI：

  10.1021/jo701868t

文献信息

• Dynamic assembly of a zinc-templated bifunctional organocatalyst in the presence of water for the asymmetric aldol reaction
  作者：Anna Serra-Pont、Ignacio Alfonso、Ciril Jimeno、Jordi Solà

  DOI：10.1039/c5cc07847d

  日期：——

  A bifunctional organocatalytic system consisting of simple pyridine ligands containing the separate catalytic functionalities was assembled using ZnCl2. This novel metal-templated catalyst furnished high yields and stereoselectivities towards the aldol...

  使用ZnCl2组装了一个双官能有机催化体系，该体系由简单的吡啶配体组成，该吡啶配体包含单独的催化官能团。这种新型的金属模板催化剂对醛醇缩合物提供了高收率和立体选择性。
• A copper-templated, bifunctional organocatalyst: a strongly cooperative dynamic system for the aldol reaction
  作者：Anna Serra-Pont、Ignacio Alfonso、Jordi Solà、Ciril Jimeno

  DOI：10.1039/c7ob01370a

  日期：——

  A copper-templated bifunctional organocatalyst delivers aldol adducts in high yields and stereoselectivities.

  一个以铜为模板的双功能有机催化剂以高产率和立体选择性提供醛醇加合物。
• Prolineamide derivatives as enhancers of learning processes and memory and pharmaceutical compositions containing same
  申请人：Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.

  公开号：EP0541497A1

  公开（公告）日：1993-05-12

  Prolinamides of formula (1) wherein R is hydrogen, R₁ is a straight or branched C₂-C₅ alkyl group, ω-substituted with a hydroxyl or carboxyl group optionally esterified with a C₂-C₅ alkanol, or an amino group substituted with one or two straight or branched C₂-C₅ alkyl groups or an amino acid residue, or a 5- or 6- membered heterocyclic group wherein the heteroatom is sulphur or nitrogen, or R and R₁ taken together form a rin of formula wherein R₃ is a phenyl group optionally substituted with halogens or halogen-substituted lower C₁-C₄ alkyl groups, and R₂ is hydrogen, benzyloxycarbonyl or formyl, are potent enhancers of learning and memory processes.

  公式（1）中的Prolinamides，其中R为氢，R₁为直链或支链C₂-C₅烷基，ω-取代基为羟基或羧基，可选择与C₂-C₅烷醇酯化，或者为一个或两个直链或支链C₂-C₅烷基或氨基酸残基取代的氨基基团，或者为一个含有硫或氮杂原子的5-或6-环杂环基团，或者R和R₁结合形成一个环，其中R₃为苯基，可选择取代卤素或卤素取代的较低C₁-C₄烷基，R₂为氢，苄氧羰基或甲酰基，是学习和记忆过程的有效增强剂。
• 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.