methyl 2-azido-2-phenylpropanoate | 148600-14-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-azido-2-phenylpropanoate
• 英文别名: Methyl 2-azido-2-phenylpropanoate
• CAS: 148600-14-0
• 化学式: C₁₀H₁₁N₃O₂
• 分子量: 205.216
• InChiKey: CVZYMADYAFRCGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 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：
  40.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-azido-2-phenylpropanoate 在 氟化氢吡啶 、 三苯基膦 、 sodium nitrite 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 methyl 2-fluoro-2-phenylpropionate
  参考文献：
  名称：

  Acide 2-fluoro-2-phényl propanoïque: préparation et utilisation comme agent chiral de dérivation

  摘要：

  The enantiomers of 2-fluoro-2-phenyl propanoic acid have been separated and their absolute configurations determined: the specific rotation of the acid with an R configuration is [alpha]20D, =-28.5-degrees (c=1.5, ethanol). This acid has been used as a chiral derivatizing agent. Esters and amides prepared from this acid and chiral alcohols or amines present important fluorine chemical shift differences between the diastereoisomers.

  DOI：

  10.1016/s0022-1139(00)80036-6
• 作为产物：
  描述：

  2-苯基丙酸 在 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 过氧化氢苯甲酰 、 chlorure de thionyle 、 四丁基溴化铵 作用下， 以 四氯化碳 为溶剂， 反应 68.0h， 生成 methyl 2-azido-2-phenylpropanoate
  参考文献：
  名称：

  Acide 2-fluoro-2-phényl propanoïque: préparation et utilisation comme agent chiral de dérivation

  摘要：

  The enantiomers of 2-fluoro-2-phenyl propanoic acid have been separated and their absolute configurations determined: the specific rotation of the acid with an R configuration is [alpha]20D, =-28.5-degrees (c=1.5, ethanol). This acid has been used as a chiral derivatizing agent. Esters and amides prepared from this acid and chiral alcohols or amines present important fluorine chemical shift differences between the diastereoisomers.

  DOI：

  10.1016/s0022-1139(00)80036-6

文献信息

• Stereospecific Synthesis of<i>sec</i>- and<i>tert</i>-Alkyl Azides from Alcohols and Trimethylsilyl Azide by a New Type of Oxidation–Reduction Condensation Using Phenyl Diphenylphosphinite and Trimethylsilylmethyl Azide
  作者：Teruaki Mukaiyama、Kiichi Kuroda、Yuji Maruyama、Yujiro Hayashi

  DOI：10.1246/cl.2008.1072

  日期：2008.10.5

  A novel method for the preparation of alkyl azides from alcohols and trimethylsilyl azide by a new type of oxidation–reduction condensation using phenyl diphenylphosphinite and trimethylsilylmethyl azide is described. Chiral secondary and tertiary alcohols are converted into the corresponding chiral azides with almost complete inversion of configuration under mild and neutral conditions.

  描述了一种利用苯基二苯基亚次膦酸酯和三甲基甲硅烷基叠氮化物通过新型氧化还原缩合从醇和三甲基甲硅烷基叠氮化物制备烷基叠氮化物的新方法。手性仲醇和叔醇在温和和中性条件下转化为相应的手性叠氮化物，构型几乎完全反转。
• Conversion of tertiary alcohols to tert-alkyl azides by way of quinone-mediated oxidation–reduction condensation using alkyl diphenylphosphinites
  作者：Kiichi Kuroda、Yujiro Hayashi、Teruaki Mukaiyama

  DOI：10.1016/j.tet.2007.03.176

  日期：2007.7

  A novel method for the preparation of alkyl azides from alcohols by way of oxidation–reduction condensation is described. In this reaction, the sterically-hindered tert-alkyl phosphinites that are prepared from the corresponding alcohols are converted into tert-alkyl azides with almost complete inversion of their stereochemistry: the obtained alkyl azides are then successfully reduced to afford the

  描述了一种通过氧化还原缩合反应从醇类制备烷基叠氮化物的新方法。在该反应中，将由相应的醇制得的空间受阻的叔烷基次膦酸酯转化为叔烷基叠氮化物，几乎完全颠倒了它们的立体化学：然后将所获得的烷基叠氮化物成功地还原，以进行相应的胺处理。因此，建立了LiAlH 4，其由相应的手性醇制备手性胺的通用方法。
• Preparation of<i>tert</i>-Alkyl Azides from Tertiary Alcohols by Way of Benzoquinone-mediated Oxidation–Reduction Condensation
  作者：Kiichi Kuroda、Nobuya Kaneko、Yujiro Hayashi、Teruaki Mukaiyama

  DOI：10.1246/cl.2006.1432

  日期：2006.12

  A novel method for the preparation of alkyl azides from alcohols by way of oxidation-reduction condensation is described. According to this reaction, the sterically hindered tert-alkyl phosphinites that are prepared from the corresponding alcohols are converted into tert-alkyl azides with almost complete inversions of their stereochemistries. On treatment with LiAlH 4 the obtained alkyl azides are

  描述了一种通过氧化还原缩合从醇类制备烷基叠氮化物的新方法。根据该反应，由相应醇制备的位阻叔烷基亚膦酸酯转化为叔烷基叠氮化物，其立体化学几乎完全颠倒。在用 LiAlH 4 处理后，所获得的烷基叠氮化物随后被成功还原，以良好的收率提供相应的胺，因此，建立了一种从相应的手性醇制备手性胺的通用方法。
• Acide 2-fluoro-2-phényl propanoïque: préparation et utilisation comme agent chiral de dérivation
  作者：S. Hamman

  DOI：10.1016/s0022-1139(00)80036-6

  日期：1993.2

  The enantiomers of 2-fluoro-2-phenyl propanoic acid have been separated and their absolute configurations determined: the specific rotation of the acid with an R configuration is [alpha]20D, =-28.5-degrees (c=1.5, ethanol). This acid has been used as a chiral derivatizing agent. Esters and amides prepared from this acid and chiral alcohols or amines present important fluorine chemical shift differences between the diastereoisomers.