N-benzyl-2,3-dihydroxypropionamide | 117471-01-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzyl-2,3-dihydroxypropionamide
• 英文别名: N-benzyl-2,3-dihydroxypropanamide
• CAS: 117471-01-9
• 化学式: C₁₀H₁₃NO₃
• 分子量: 195.218
• InChiKey: PNVAZIPJZUUYBY-UHFFFAOYSA-N

物化性质

• 沸点：
  490.2±45.0 °C(Predicted)
• 密度：
  1.246±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-benzyl-2,3-dihydroxypropionamide 在 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 2,3-epoxy-N-(phenylmethyyl)propanamide
  参考文献：
  名称：

  The anticonvulsant activities of N-benzyl 3-methoxypropionamides

  摘要：

  We recently reported that the ED(50) value for (R,S)-2,3-dimethoxypropionamide (1) in the maximal electroshock (MES)induced seizure test in mice was 30 mg/kg (Choi, D.; Stables, J.P., Kohn, H. Bioorg. Med. Chem. 1996, 4, 2105). This value is comparable to that observed for phenobarbital (ED(50) = 22 mg/kg). Compound 1 is structurally similar to a class of MES-selective anticonvulsant agents, termed functionalized amino acids (2), that were developed in our laboratory. The distinguishing feature of 2 is the differential activities observed for enantiomers. In this study, we asked whether comparable differences in activities were observed in the MES-induced seizure test for (R)- and (S)-1. We developed stereospecific syntheses for these enantiomers and showed that both compounds exhibit nearly equal anticonvulsant activity in mice (ip) (MES ED(50) = 79-111 mg/kg). The surprisingly high ED(50) values for (R)- and (S)-1 required our redetermining the ED(50) value for (R,S)-1. We revised this value to 79 mg/kg. A limited structure-activity relationship study for 1 was conducted. Special attention was given to the C(2) methoxy unit in 1. We found that replacement of this moiety led to only modest differences in the MES activities upon ip administration to mice. Significantly we observed an enhancement in the anticonvulsant activity for (R,S)-N-benzyl 2-hydroxy-3-methoxypropionamide ((R,S)-6) upon oral administration to rats ((R,S)-6: mice tip) ED(50) > 100, < 300 mg/kg; rat (oral) ED(50) = 62 mg/kg), The activities of 3-methoxypropionamides, functionalized amino acids, and related compounds are discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00186-8
• 作为产物：
  描述：

  苄胺 以65%的产率得到N-benzyl-2,3-dihydroxypropionamide
  参考文献：
  名称：

  Propionamide anticonvulsants

  摘要：

  本发明涉及以下式的化合物：##STR1## 包含相同化合物的医药组合物以及其作为抗癫痫药物的用途。

  公开号：

  US05880158A1

文献信息

• Metal-Ligand Cooperation in the Catalytic Dehydrogenative Coupling (DHC) of Polyalcohols to Carboxylic Acid Derivatives
  作者：Mónica Trincado、Klaus Kühlein、Hansjörg Grützmacher

  DOI：10.1002/chem.201101084

  日期：2011.10.10

  Several polyols, which are easily available from sugars through biochemical conversion or hydrogenolytic cleavage, are directly converted into carboxylic acids and amides. This efficient dehydrogenative coupling process, catalyzed by a rhodium(I) diolefin amido complex, is an attractive approach for the production of organic fine chemicals from renewable resources. This method tolerates the presence

  通过生化转化或氢解裂解可从糖中轻松获得的几种多元醇可直接转化为羧酸和酰胺。由铑（I）二烯烃酰胺基络合物催化的这种有效的脱氢偶联方法是一种由可再生资源生产有机精细化学品的有吸引力的方法。该方法可以容忍多个羟基的存在，并且可以扩展到在温和条件下由相应的氨基醇直接合成内酰胺的方法。
• Metal‐Catalyst‐Free One‐Pot Aqueous Synthesis of <i>trans</i>‐1,2‐Diols from Electron‐Deficient <i>α</i>,<i>β</i>‐Unsaturated Amides via Epoxidation Using Oxone as a Dual Role Reagent
  作者：Ming‐Zhong Zhang、Ping Wang、Hai‐Yan Liu、Dailian Wang、Ya Deng、Yu‐Heng Bai、Fei Luo、Wen‐Yu Wu、Tieqiao Chen

  DOI：10.1002/cssc.202300583

  日期：2023.9.22

  First general one-pot direct trans-dihydroxylation of electron-deficient α,β-unsaturated amides was developed. Trans-1,2-diols were produced, rather than cyclizing nitrogen-containing heterocycles by using inorganic oxone as a dual-role reagent in water. This reaction allowed operational simplicity, switchable selectivity, broad substrate scope, no metal pollution and organic waste generation.

  开发了第一个缺电子α , β-不饱和酰胺的通用一锅法直接反式二羟基化反应。通过使用无机过硫酸氢钾作为水中的双作用试剂来生产反式-1,2-二醇，而不是环化含氮杂环。该反应操作简单、选择性可切换、底物范围广泛、无金属污染和有机废物产生。
• The anticonvulsant activities of functionalized N-benzyl 2-acetamidoacetamides. The importance of the 2-acetamido substituent
  作者：Daeock Choi、James P Stables、Harold Kohn

  DOI：10.1016/s0968-0896(96)00225-8

  日期：1996.12

  Recent studies have demonstrated that substituted N-benzyl 2-acetamidoacetamides provide significant protection against maximal electroshock (MES)-induced seizures in mice and rats. In this study, we investigated whether the 2-acetamido moiety was necessary for anticonvulsant activity. Ten derivatives of the known anticonvulsant, N-benzyl 2-acetamido-2-phenyl acetamide were prepared in which the 2-acetamido group was replaced by hydrogen, methyl, oxygen, and halogen substituents. Evaluation of these compounds in the MES-induced seizure test demonstrated that both the hydroxy and the methoxy compounds provided full protection against MES-induced seizures in mice given ip at 100 mg/kg. Moreover, evaluation of the individual stereoisomers for the hydroxy compound showed that the principal activity resided in the (R)-isomer. These findings demonstrated that the 2-acetamido substituent is important but not obligatory for the prevention of MES-induced seizures. Further supporting evidence was provided by comparing the pharmacological activities of N-benzyl 2,3-dimethoxypropionamide with N-benzyl 2-acetamido-3-methoxypropionamide. The ED(50) value for the former in the MES test was 30 mg/kg (ip), which compared favorably with phenobarbital (ED(50) = 22 mg/kg), but the ED(50) value for N-benzyl 2-acetamido-3-methoxypropionamide was 8.3 mg/kg. Copyright (C) 1996 Elsevier Science Ltd
• US5880158A
  申请人：——

  公开号：US5880158A

  公开（公告）日：1999-03-09
• [EN] PROPIONAMIDE DERIVATIVES AND THEIR USE AS ANTICONVULSANTS<br/>[FR] DERIVES DE PROPIONAMIDE ET LEUR UTILISATION COMME ANTICONVULSIFS
  申请人：RESEARCH CORPORATION TECHNOLOGIES, INC.

  公开号：WO1998013336A1

  公开（公告）日：1998-04-02

  (EN) The present invention is directed to a compound useful as an anticonvulsant. The compound has formula (I); X2R1 when X2=S, HX2R1 when X2=S.(FR) La présente invention concerne un composé utilisé en tant qu'anticonvulsif. Le composé est de formule (I), X2R1 lorsque X2=S, HX2R1 lorsque X2=S.