(S)-(+)-2-叠氮基-1-(4-甲氧基苯基)-1-乙酸乙酯 | 349642-77-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (S)-(+)-2-叠氮基-1-(4-甲氧基苯基)-1-乙酸乙酯
• 英文名称: (S)-(+)-2-azido-1-(4-methoxyphenyl)-1-ethyl acetate
• 英文别名: (S)-(+)-2-azido-1-(4-methoxyphenyl)ethyl acetate；[(1S)-2-azido-1-(4-methoxyphenyl)ethyl] acetate
• CAS: 349642-77-9
• 化学式: C₁₁H₁₃N₃O₃
• 分子量: 235.243
• InChiKey: DYVHCKMBZSDMHM-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  49.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-(+)-2-叠氮基-1-(4-甲氧基苯基)-1-乙酸乙酯 在 palladium on activated charcoal 氢气 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 7.0h， 生成 (S)-N-[2-hydroxy-2-(4-methoxyphenyl)ethyl]benzamide
  参考文献：
  名称：

  Chemoenzymatic synthesis of (R)- and (S)-tembamide, aegeline and denopamine by a one-pot lipase resolution protocol

  摘要：

  An efficient synthesis of optically active beta-azido alcohols from their ketoazides by a one-pot reduction and an in situ lipase resolution protocol is described. The synthetic utility of this procedure has been illustrated by its application in the practical synthesis of both enantiomers of the natural hydroxyamides, tembamide, aegeline and the cardiac drug denopamine, with high enantioselectivities. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.013
• 作为产物：
  描述：

  2-叠氮基-1-(4-甲氧基苯基)乙酮 在 aluminum oxide 、 sodium tetrahydroborate 、 Pseudomonas cepacia lipase immobilized on ceramic particles 作用下， 以 异丙醚 为溶剂， 反应 22.0h， 生成 (S)-(+)-2-叠氮基-1-(4-甲氧基苯基)-1-乙酸乙酯
  参考文献：
  名称：

  Chemoenzymatic synthesis of (R)- and (S)-tembamide, aegeline and denopamine by a one-pot lipase resolution protocol

  摘要：

  An efficient synthesis of optically active beta-azido alcohols from their ketoazides by a one-pot reduction and an in situ lipase resolution protocol is described. The synthetic utility of this procedure has been illustrated by its application in the practical synthesis of both enantiomers of the natural hydroxyamides, tembamide, aegeline and the cardiac drug denopamine, with high enantioselectivities. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.013

文献信息

• Chemoenzymatic Resolution of β-Azidophenylethanols by<i>Candida antarctica</i>and their Application for the Synthesis of Chiral Benzotriazoles
  作者：Lenilson C. Rocha、Isac G. Rosset、Gliseida Z. Melgar、Cristiano Raminelli、André L. M. Porto、Alex H. Jeller

  DOI：10.5935/0103-5053.20130181

  日期：——

  The kinetic resolutions of (±)-β-azidophenylethanols were carried out using lipase from Candida antarctica, and enantiomerically enriched (R)-β-azidophenylethanols and their corresponding (S)-β-azidophenylethyl acetates were obtained in good enantiomeric excesses (up to > 99%). The enantiomerically enriched (R)-β-azidophenylethanols were subjected to cyclization reaction with 2-(trimethylsilyl)phenyl

  使用来自南极假丝酵母的脂肪酶进行（±）-β-叠氮基苯乙醇的动力学拆分，得到对映体富集的（R）-β-叠氮基苯乙醇及其相应的（S）-β-叠氮基苯乙酸乙酯，其对映体过量良好（最高可达> 99％）。使对映体富集的（R）-β-叠氮基苯乙醇与2-（三甲基甲硅烷基）苯基三氟甲磺酸酯和CsF进行环化反应，以[3 + 2]的高收率（75-86％）生成手性1,2,3-苯并三唑化合物环加成，其中涉及苯炔形成。
• Non-enzymatic kinetic resolution of 1,2-azidoalcohols using a planar-chiral DMAP derivative catalyst
  作者：Laura Mesas-Sánchez、Alba E. Díaz-Álvarez、Peter Dinér

  DOI：10.1016/j.tet.2012.10.077

  日期：2013.1

  Optically pure 1,2-azidoalcohols are widely used as precursors for other high value organic products. A non-enzymatic kinetic resolution procedure for the stereoselective synthesis of chiral 1,2-azidoalcohols from the readily available racemic counterparts has been developed, employing a planar-chiral DMAP derivative catalyst. Following this procedure, a range of aromatic 1,2-azidoalcohols was obtained in good selectivities (up to S=45) and high enantiomeric excess (up to 99% ee). (c) 2012 Elsevier Ltd. All rights reserved.
• Stereoselective acylations of 1,2-azidoalcohols with vinyl acetate, catalyzed by lipase Amano PS
  作者：Eugênia Cristina Souza Brenelli、Jane Luiza Nogueira Fernandes

  DOI：10.1016/s0957-4166(03)00206-4

  日期：2003.5

  Lipase PS-catalyzed kinetic resolution of vicinal azidoalcohols was accomplished. The enzymatic reaction rates and the enantioselectivities were significantly enhanced under the ultrasonic irradiation. (C) 2003 Elsevier Science Ltd. All rights reserved.