(S)-N-benzyl 2,3-dihydroxypropionamide | 205122-64-1

• 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: (S)-N-benzyl 2,3-dihydroxypropionamide
• 英文别名: (S)-N-benzyl-2,3-dihydroxypropanamide；(2S)-N-benzyl-2,3-dihydroxypropanamide
• CAS: 205122-64-1
• 化学式: C₁₀H₁₃NO₃
• 分子量: 195.218
• InChiKey: PNVAZIPJZUUYBY-VIFPVBQESA-N

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：

  (S)-N-benzyl 2,3-dihydroxypropionamide 在 二正丁基氧化锡 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 (S)-N-benzyl-2-hydroxy-3-methoxypropanamide
  参考文献：
  名称：

  A Non-infringing Route for Enantioselective Synthesis of Antiepileptic Agent Lacosamide

  摘要：

  A non-infringing route for enantioselective synthesis of lacosamide has been developed. The synthesis started from commercially available acrylic acid and was completed in eight steps using Sharpless asymmetric dihydroxylation as a key step with an overall yield of 29%. All the reactions were very clean with good yields.

  DOI：

  10.1055/s-0033-1339901
• 作为产物：
  描述：

  N-苄基丙烯酰胺 在 甲基磺酰胺 、 AD-mix-β 作用下， 以 水 、 叔丁醇 为溶剂， 反应 48.0h， 以80%的产率得到(S)-N-benzyl 2,3-dihydroxypropionamide
  参考文献：
  名称：

  A Non-infringing Route for Enantioselective Synthesis of Antiepileptic Agent Lacosamide

  摘要：

  A non-infringing route for enantioselective synthesis of lacosamide has been developed. The synthesis started from commercially available acrylic acid and was completed in eight steps using Sharpless asymmetric dihydroxylation as a key step with an overall yield of 29%. All the reactions were very clean with good yields.

  DOI：

  10.1055/s-0033-1339901

文献信息

• Vicinal diol cyclic sulfates. Like epoxides only more reactive
  作者：Yun. Gao、K. Barry. Sharpless

  DOI：10.1021/ja00230a045

  日期：1988.10

  Preparation de dioxyde-2,2 de dioxathiolannes-1,3,2(I) a partir de glycols et reactions des sulfates cycliques(I) avec divers nucleophiles (H − , N 3 − , F − , PhCO 2 − , NO 3 − , SCN − , PhCH 2 − )

  制备 de dioxyde-2,2 de dioxathiolannes-1,3,2(I) a partir deglycols et 反应 脱硫酸盐 cycliques(I) avec divers 亲核试剂 (H - , N 3 - , F - , PhCO 2 - , NO 3 − , SCN − , PhCH 2 − )
• Propionamide anticonvulsants
  申请人：Research Corporation Tech., Inc.

  公开号：US05880158A1

  公开（公告）日：1999-03-09

  The present invention is directed to a compound of the following formula: ##STR1## pharmaceutical compositions containing the same and the use thereof as an anticonvulsant.

  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。
• 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.
• GAO, YUN;SHARPLESS, K. BARRY, J. AMER. CHEM. SOC., 110,(1988) N2, C. 7538-7539
  作者：GAO, YUN、SHARPLESS, K. BARRY

  DOI：——

  日期：——
• US5880158A
  申请人：——

  公开号：US5880158A

  公开（公告）日：1999-03-09