(2R,3R)-3-Azido-3-(4-methoxy-phenyl)-propane-1,2-diol | 237736-22-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2R,3R)-3-Azido-3-(4-methoxy-phenyl)-propane-1,2-diol
• 英文别名: (2R,3R)-3-azido-3-(4-methoxyphenyl)propane-1,2-diol
• CAS: 237736-22-0
• 化学式: C₁₀H₁₃N₃O₃
• 分子量: 223.232
• InChiKey: VBYQPQUDUBFJNW-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  64
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-Azido-3-(4-methoxy-phenyl)-propane-1,2-diol 在 吡啶 、 咪唑 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (4R,5R)-5-(tert-butyldiphenylsilyloxymethyl)-4-(4-methoxyphenyl)oxazolidin-2-one
  参考文献：
  名称：

  Stereoselective syntheses of cytoxazone, a novel cytokine modulator, and its stereoisomers

  摘要：

  Cytoxazone, a novel cytokine modulator, and its stereoisomers were stereoselectively synthesized via stereocontrolled introduction of an azide group and direct construction of the 2-oxazolidinone ring from an azide carbonate by reductive cyclization. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00712-1
• 作为产物：
  描述：

  (1S,2S)-3-(tert-Butyl-diphenyl-silanyloxy)-1-(4-methoxy-phenyl)-propane-1,2-diol 在 氯化亚砜 、 叠氮化锂 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2R,3R)-3-Azido-3-(4-methoxy-phenyl)-propane-1,2-diol
  参考文献：
  名称：

  Stereoselective syntheses of cytoxazone, a novel cytokine modulator, and its stereoisomers

  摘要：

  Cytoxazone, a novel cytokine modulator, and its stereoisomers were stereoselectively synthesized via stereocontrolled introduction of an azide group and direct construction of the 2-oxazolidinone ring from an azide carbonate by reductive cyclization. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00712-1

文献信息

• NaIO4-mediated asymmetric bromohydroxylation of α,β-unsaturated carboxamides with high diastereoselectivity: a short route to (−)-cytoxazone and droxidopa
  作者：Shyla George、Srinivasarao V. Narina、Arumugam Sudalai

  DOI：10.1016/j.tetlet.2006.12.109

  日期：2007.2

  The NaIO4-mediated asymmetric bromohydroxylation of alpha,beta-unsaturated carboxamides was achieved using lithium bromide as the bromine source under acidic conditions at rt to afford the corresponding chiral alpha-bromo-beta-hydroxy carboxamides. Excellent yields (77-90%) and diastereoselectivities (up to 10:1) along with exclusive control over regio- as well as anti-selectivity are the main features with a good scope of substrates. The method has successfully been applied in the enantioselective syntheses of two biologically important molecules, viz (-)-cytoxazone and L-threo-DOPS (droxidopa). (c) 2007 Elsevier Ltd. All rights reserved.
• [EN] ONE STEP PROCESS FOR THE SYNTHESIS OF AZIDO ALCOHOLS FROM ALKENE<br/>[FR] PROCÉDÉ EN UNE ÉTAPE POUR LA SYNTHÈSE D'AZIDO-ALCOOLS À PARTIR D'ALCÈNE
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2016113764A1

  公开（公告）日：2016-07-21

  The present invention relates to one step room temperature process for the synthesis of azido alcohols from alkenes. More particularly, I2 catalysed a regio and diastereo selective one step room temperature process for the synthesis of 1,2-azido alcohols from alkenes.