(2R,3R)-2-Azidomethyl-3-phenyl-oxirane

• 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: (2R,3R)-2-Azidomethyl-3-phenyl-oxirane
• 英文别名: (2R,3R)-2-(azidomethyl)-3-phenyloxirane
• 化学式: C₉H₉N₃O
• 分子量: 175.19
• InChiKey: LVLSBJGWOLNMDW-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  26.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2-Azidomethyl-3-phenyl-oxirane 在 水 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以91%的产率得到C-((2R,3R)-3-Phenyl-oxiranyl)-methylamine
  参考文献：
  名称：

  Rearrangement of primary 2,3-epoxy amines into 1,2-aziridinyl 3-ols.

  摘要：

  Conditions were found to transform primary 2,3-epoxy amines into 1,2-aziridinyl 3-ols which involve an intramolecular opening of the epoxide ring mediated by trimethylaluminum.

  DOI：

  10.1016/s0040-4039(00)79090-3
• 作为产物：
  描述：

  tert-butyl-[[(4S,5S)-2,2-dioxo-5-phenyl-1,3,2-dioxathiolan-4-yl]methoxy]-dimethylsilane 在 四丁基氟化铵 、 sodium azide 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 21.5h， 生成 (2R,3R)-2-Azidomethyl-3-phenyl-oxirane
  参考文献：
  名称：

  The synthesis of (R,S)-reboxetine employing a tandem cyclic sulfate rearrangement—opening process

  摘要：

  (R,S)-Reboxetine was synthesized in nine steps and with 43% overall yield starting from trans-cinnamyl alcohol. Following silylation and AD steps, the two hydroxyl groups at C-1 and C-2 were simultaneously activated to the cyclic sulfate. A series of tandem reactions initiated by desilylation transposed the activation to C-3, then to C-1, where nucleophilic displacements took place in succession. During this process, the configuration at C-2 was inverted while that at C-1 was retained through a double inversion. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.04.018

文献信息

• Zinc Azide Mediated Mitsunobu Substitution. An Expedient Method for the One-Pot Azidation of Alcohols
  作者：Marie Claude Viaud、Patrick Rollin

  DOI：10.1055/s-1990-26809

  日期：——

  In the presence of the diisopropyl azodicarboxylate/triphenylphosphine couple, alcohols react with zinc azide/bis-pyridine complex to give various azides via a Mitsunobu-type substitution.

  在偶氮二羧酸二异丙酯/三苯基膦的存在下，醇与叠氮化锌/双吡啶配合物反应，通过米苏诺布型取代生成各种叠氮化合物。
• β-Fluoroamphetamines via the Stereoselective Synthesis of Benzylic Fluorides
  作者：Alexander J. Cresswell、Stephen G. Davies、James A. Lee、Paul M. Roberts、Angela J. Russell、James E. Thomson、Melloney J. Tyte

  DOI：10.1021/ol100862s

  日期：2010.7.2

  A range of substituted aryl epoxides undergo efficient ring-opening hydrofluorination upon treatment with 0.33 equiv of BF3 center dot OEt2 in CH2Cl2 at -20 degrees C to give the corresponding syn-fluorohydrins, consistent with a mechanism involving a stereoselective S(N)1-type epoxide ring-opening process. The benzylic fluoride products of these reactions are valuable templates for further elaboration, as demonstrated by the preparation of a range of aryl-substituted beta-fluoroamphetamines.
• A One‐Pot Process toward 2‐Hydroxy‐1,3‐diamino Compounds: A Synthetic Application to Dual Norepinephrine/Serotonin Reuptake Inhibitors
  作者：Nagum Lee、Seung Hyun Oh、Soo Y. Ko

  DOI：10.1002/bkcs.10111

  日期：2015.2
• The synthesis of (R,S)-reboxetine employing a tandem cyclic sulfate rearrangement—opening process
  作者：Jin Yu、Soo Y. Ko

  DOI：10.1016/j.tetasy.2012.04.018

  日期：2012.5

  (R,S)-Reboxetine was synthesized in nine steps and with 43% overall yield starting from trans-cinnamyl alcohol. Following silylation and AD steps, the two hydroxyl groups at C-1 and C-2 were simultaneously activated to the cyclic sulfate. A series of tandem reactions initiated by desilylation transposed the activation to C-3, then to C-1, where nucleophilic displacements took place in succession. During this process, the configuration at C-2 was inverted while that at C-1 was retained through a double inversion. (C) 2012 Elsevier Ltd. All rights reserved.
• Rearrangement of primary 2,3-epoxy amines into 1,2-aziridinyl 3-ols.
  作者：Rachida Najime、Serge Pilard、Michel Vaultier

  DOI：10.1016/s0040-4039(00)79090-3

  日期：1992.9

  Conditions were found to transform primary 2,3-epoxy amines into 1,2-aziridinyl 3-ols which involve an intramolecular opening of the epoxide ring mediated by trimethylaluminum.