(RS)-N-benzyl 2-(pyridin-2-yl)acetamide | 107776-92-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (RS)-N-benzyl 2-(pyridin-2-yl)acetamide
• 英文别名: N-benzyl-2-(pyridin-2-yl)acetamide；N-benzyl-2-pyridin-2-yl-acetamide；[2]pyridyl-acetic acid benzylamide；[2]Pyridyl-essigsaeure-benzylamid；Pyridyl-(2)-essigsaeure-(N-benzyl-amid)；Pyridin-2-essigsaeure-N-benzylamid；N-Benzyl(2-pyridyl)acetamide；N-benzyl-2-pyridin-2-ylacetamide
• CAS: 107776-92-1
• 化学式: C₁₄H₁₄N₂O
• 分子量: 226.278
• InChiKey: PELWENYNXIJWRI-UHFFFAOYSA-N

物化性质

• 熔点：
  76.5-77.5 °C(Solv: ethyl ether (60-29-7); ligroine (8032-32-4))
• 沸点：
  460.7±38.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (RS)-N-benzyl 2-(pyridin-2-yl)acetamide 在 盐酸 、 甲酸铵 、 溶剂黄146 、 锌 、 sodium nitrite 作用下， 以 甲醇 、 水 为溶剂， 反应 7.0h， 生成 (RS)-N-benzyl 2-amino-2-(pyridin-2-yl)acetamide hydrochloride
  参考文献：
  名称：

  Synthesis, anticonvulsant activity, and neuropathic pain-attenuating activity of N-benzyl 2-amino-2-(hetero)aromatic acetamides

  摘要：

  N-Benzyl 2-acetamido-2-substituted acetamides, where the 2-substituent is a (hetero) aromatic moiety, are potent anticonvulsants. We report the synthesis and whole animal pharmacological evaluation of 16 analogues where the terminal 2-acetyl group was removed to give the corresponding primary amino acid derivatives (PAADs). Conversion to the PAAD structure led to a substantial drop in seizure protection in animal tests, demonstrating the importance of the N-acetyl moiety for anticonvulsant activity. However, several of the PAADs displayed notable pain-attenuating activities in a mouse model. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.002
• 作为产物：
  描述：

  2-吡啶乙酸乙酯 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 2.0h， 生成 (RS)-N-benzyl 2-(pyridin-2-yl)acetamide
  参考文献：
  名称：

  Synthesis, anticonvulsant activity, and neuropathic pain-attenuating activity of N-benzyl 2-amino-2-(hetero)aromatic acetamides

  摘要：

  N-Benzyl 2-acetamido-2-substituted acetamides, where the 2-substituent is a (hetero) aromatic moiety, are potent anticonvulsants. We report the synthesis and whole animal pharmacological evaluation of 16 analogues where the terminal 2-acetyl group was removed to give the corresponding primary amino acid derivatives (PAADs). Conversion to the PAAD structure led to a substantial drop in seizure protection in animal tests, demonstrating the importance of the N-acetyl moiety for anticonvulsant activity. However, several of the PAADs displayed notable pain-attenuating activities in a mouse model. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.002

文献信息

• [EN] IMIDAZOPYRIMIDINE COMPOUNDS USEFUL FOR THE TREATMENT OF CANCER<br/>[FR] COMPOSÉS D'IMIDAZOPYRIMIDINE UTILES POUR LE TRAITEMENT DU CANCER
  申请人：NOVARTIS AG

  公开号：WO2017221100A1

  公开（公告）日：2017-12-28

  A compound of Formula (IA), or a pharmaceutically acceptable salt thereof, is provided that has been shown to be useful for treating a PRC2-mediated disease or disorder: wherein A, R3, R4, R6, and R7 are as defined herein.

  提供了一种具有以下结构式（IA）的化合物，或其药用盐，已被证明对治疗PRC2介导的疾病或紊乱有用：其中A，R3，R4，R6和R7如本文所定义。
• Metal-free synthesis of imidazo[1,5-<i>a</i>]pyridines <i>via</i> elemental sulfur mediated sequential dual oxidative Csp³–H amination
  作者：Jie Sheng、Jidan Liu、He Zhao、Liyao Zheng、Xingchuan Wei

  DOI：10.1039/c8ob01391h

  日期：——

  A simple and efficient approach has been developed for the synthesis of imidazo[1,5-a]pyridines using the elemental sulfur mediated sequential dual oxidative Csp3–H amination of 2-pyridyl acetates and amines under metal- and peroxide-free conditions. Broad substrate scope, operational simplicity and gram-scale ability make this chemistry very practical.

  已经开发了一种简单有效的方法，用于在无金属和无过氧化物的条件下，使用元素硫介导的乙酸2-吡啶酯和胺的连续双氧化Csp 3 -H胺化来合成咪唑并[1,5- a ]吡啶。广泛的底物范围，操作简便和克级能力使这种化学非常实用。
• Metal-Free Aminothiation of Alkynes: Three-Component Tandem Annulation toward Indolizine Thiones from 2-Alkylpyridines, Ynals, and Elemental Sulfur
  作者：Zhengwang Chen、Pei Liang、Fan Xu、Zhen Deng、Lipeng Long、Guotian Luo、Min Ye

  DOI：10.1021/acs.joc.9b01802

  日期：2019.10.4

  A metal-free three-component annulation reaction for the synthesis of indolizine thiones via tandem C-C/C-N/C-S bond formation was developed. Various 2-alkylpyridines with aromatic ynals and elemental sulfur proceeded smoothly under catalyst-free conditions, and the desired products were obtained in moderate to excellent yields.

  开发了一种无金属的三组分环化反应，用于通过串联CC / CN / CS键的形成来合成吲哚嗪硫酮。在无催化剂的条件下，各种带有芳族乙醛和元素硫的2-烷基吡啶均能顺利进行，并以中等至极好的收率获得了所需的产物。
• Stereodivergent Allylation of Azaaryl Acetamides and Acetates by Synergistic Iridium and Copper Catalysis
  作者：Xingyu Jiang、Philip Boehm、John F. Hartwig

  DOI：10.1021/jacs.7b12824

  日期：2018.1.31

  We report stereodivergent allylic substitution reactions of allylic esters with prochiral enolates derived from azaaryl acetamides and acetates to form products from addition of the enolates at the most substituted carbon of an allyl moiety with two catalysts, a chiral metallacyclic iridium complex and a chiral bisphosphine-ligated copper(I) complex, which individually control the configuration of

  我们报道了烯丙酯与衍生自氮杂芳基乙酰胺和乙酸酯的前手性烯醇化物的立体发散烯丙基取代反应，通过使用两种催化剂（手性金属环铱络合物和手性双膦配位物）在烯丙基部分取代最多的碳上加成烯醇化物而形成产物铜(I)配合物，分别单独控制亲电子和亲核碳原子的构型。通过两种催化剂对映异构体的简单排列，分别合成了含有两个立构中心的产物的所有四种立体异构体，具有高非对映选择性和对映选择性。多种带有吡啶基、苯并噻唑基、苯并恶唑基、吡嗪基、喹啉基和异喹啉基部分的氮杂芳基乙酰胺和乙酸酯都被发现适合于这种转化。
• Stereodivergent Construction of Tertiary Fluorides in Vicinal Stereogenic Pairs by Allylic Substitution with Iridium and Copper Catalysts
  作者：Zhi-Tao He、Xingyu Jiang、John F. Hartwig

  DOI：10.1021/jacs.9b04440

  日期：2019.8.21

  enantioselective synthesis of tertiary alkyl fluorides, the synthesis of compounds containing such a stereogenic center within an array of stereocenters, particularly two vicinal ones, remains a synthetic challenge, and no method to control the configuration of each stereogenic center independently has been reported. We describe a strategy to achieve such a stereodivergent synthesis of vicinal stereogenic centers

  尽管在叔烷基氟化物的对映选择性合成上付出了很多努力，但在一系列立体中心，特别是两个相邻的立体中心中，合成含有这种立体中心的化合物仍然是一个合成挑战，并且没有方法控制每个立体中心的构型中心独立报道。我们描述了一种策略，通过与包含控制亲电子碳构型的铱络合物和铜催化剂的催化剂体系形成连接碳-碳键，实现邻位立体中心的这种立体发散合成，其中一个包含氟原子。控制亲核含氟碳的构型。这些反应以高产率、非对映选择性和对映选择性（通常>90% 产率，>20:1 dr，99% ee）与烷基和芳基取代的烯丙基酯以及未稳定的氮杂芳基酮、酯和酰胺的烯醇化物发生。访问产品的所有四种立体异构体证明了对两种配置的独立精确控制。这种方法扩展到以同样高产率和选择性的邻位四级和三级立体中心的立体发散构建。DFT 计算揭示了烯丙基取代中烯醇铜的立体选择性的起源。访问产品的所有四种立体异构体证明了对两种配置的独立精确控制。这种方法扩