o-nitrophenyl-2 phenyl-3 oxiranne | 31356-08-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: o-nitrophenyl-2 phenyl-3 oxiranne
• 英文别名: (2S,3S)-2-(2-nitrophenyl)-3-phenyloxirane；2-Nitrostilbenoxid
• CAS: 31356-08-8；31448-69-8；53774-34-8；83915-70-2
• 化学式: C₁₄H₁₁NO₃
• 分子量: 241.246
• InChiKey: NXUBDSJOSBLAMH-KBPBESRZSA-N

物化性质

• 沸点：
  366.2±30.0 °C(Predicted)
• 密度：
  1.307±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  58.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  o-nitrophenyl-2 phenyl-3 oxiranne 在 Amberlist 15 作用下， 以 水 为溶剂， 生成 R*R*-2-phenyl-1-(2-nitrophenyl)-1,2-ethanediol
  参考文献：
  名称：

  A mild access to chiral syn 1,2-diaryl glycols by stereoselective ring opening of ortho substituted trans 2,3-diaryl-oxiranes using Amberlyst 15 in H2O/THF system

  摘要：

  Amberlyst 15 was an efficient and green catalyst for the reaction of 2,3-diaryloxiranes with H2O in organic co-solvent to prepare glycols in high yield. Ortho substituted trans 2,3-diaryloxiranes afforded the corresponding syn glycols stereo- and enantiospecifically. Stereoselectivity appeared related to the coordination ability of the substituents, irrespective of their electronic properties. Indeed o-OCH3 and o-OBn substituted syn glycols were obtained in high stereochemical ratios (6/1 and 10/1, respectively), and o-OTIPS and o-NO2 substituted ones were obtained as exclusive products, with the same ee of the parent epoxides. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.06.039
• 作为产物：
  描述：

  2-硝基苄溴 在 sodium hydroxide 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 26.0h， 生成 o-nitrophenyl-2 phenyl-3 oxiranne
  参考文献：
  名称：

  Stanc, Yannick Le; Corre, Maurice Le, Canadian Journal of Chemistry, 1985, vol. 63, p. 2958 - 2960

  摘要：

  DOI：

文献信息

• A mild access to chiral syn 1,2-diaryl glycols by stereoselective ring opening of ortho substituted trans 2,3-diaryl-oxiranes using Amberlyst 15 in H2O/THF system
  作者：Paolo Lupattelli、Lucia Chiummiento、Maria Funicello、Francesco Tramutola、Antonella Marmo、Natascia Gliubizzi、Daniela Tofani

  DOI：10.1016/j.tet.2015.06.039

  日期：2015.8

  Amberlyst 15 was an efficient and green catalyst for the reaction of 2,3-diaryloxiranes with H2O in organic co-solvent to prepare glycols in high yield. Ortho substituted trans 2,3-diaryloxiranes afforded the corresponding syn glycols stereo- and enantiospecifically. Stereoselectivity appeared related to the coordination ability of the substituents, irrespective of their electronic properties. Indeed o-OCH3 and o-OBn substituted syn glycols were obtained in high stereochemical ratios (6/1 and 10/1, respectively), and o-OTIPS and o-NO2 substituted ones were obtained as exclusive products, with the same ee of the parent epoxides. (C) 2015 Elsevier Ltd. All rights reserved.
• Stanc, Yannick Le; Corre, Maurice Le, Canadian Journal of Chemistry, 1985, vol. 63, p. 2958 - 2960
  作者：Stanc, Yannick Le、Corre, Maurice Le

  DOI：——

  日期：——