N-benzyl-2,2-dimethyl-1,3-dioxolane-4-carboxamide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-benzyl-2,2-dimethyl-1,3-dioxolane-4-carboxamide
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: MENCBVQIBKVVJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苄胺 、 丙酮缩甘油 在 3-甲基-2-丁酮 、 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 caesium carbonate 、 1,4-双(二苯基膦)丁烷 作用下， 以 叔丁醇 为溶剂， 反应 24.0h， 以40%的产率得到N-benzyl-2,2-dimethyl-1,3-dioxolane-4-carboxamide
  参考文献：
  名称：

  Ruthenium-catalysed oxidation of alcohols to amides using a hydrogen acceptor

  摘要：

  A wider investigation into the synthesis of secondary amides from primary alcohols using a hydrogen acceptor using commercially available [Ru(p-cymene)Cl-2](2) with bis(diphenylphosphino)butane (dppb) as the catalyst. The report looks at over 50 examples with varying functionality and steric bulk, whilst also covering the first reported results using microwave heating to effect the transformation. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.04.017

文献信息

• The anticonvulsant activities of N-benzyl 3-methoxypropionamides
  作者：Shridhar V. Andurkar、James P. Stables、Harold Kohn

  DOI：10.1016/s0968-0896(99)00186-8

  日期：1999.11

  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.
• 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.