(E)-3-nitro-5-phenylpent-2-ene | 377080-66-5

• 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: (E)-3-nitro-5-phenylpent-2-ene
• 英文别名: [(E)-3-nitropent-3-enyl]benzene
• CAS: 377080-66-5
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: VJUNXEPUOBNPSR-BIIKFXOESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-nitro-5-phenylpent-2-ene 在 18-冠醚-6 、 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 、 氨 、 三正丁基氢锡 、 lithium 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.83h， 生成 (S)-2-amino-5-phenylpentane
  参考文献：
  名称：

  Enantioselective synthesis of α,α-disubstituted amines from nitroalkenes

  摘要：

  Disubstituted nitroalkenes were converted into enantiomerically enriched amines (isolated as their hydrochloride salts) with enantiomeric excesses of 88 to > 95% in three steps: (a) highly stereoselective conjugate addition of the potassium salt of 4-phenyloxazolidin-2-one; (b) radical-mediated removal of the nitro group: (c) cleavage of the oxazolidinone. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00323-8
• 作为产物：
  描述：

  1-硝基-3-苯基丙烷 在 4-二甲氨基吡啶 、 氢氧化钾 、 乙酸酐 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 48.33h， 生成 (E)-3-nitro-5-phenylpent-2-ene
  参考文献：
  名称：

  Enantioselective synthesis of α,α-disubstituted amines from nitroalkenes

  摘要：

  Disubstituted nitroalkenes were converted into enantiomerically enriched amines (isolated as their hydrochloride salts) with enantiomeric excesses of 88 to > 95% in three steps: (a) highly stereoselective conjugate addition of the potassium salt of 4-phenyloxazolidin-2-one; (b) radical-mediated removal of the nitro group: (c) cleavage of the oxazolidinone. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00323-8

文献信息

• Enantioselective synthesis of α,α-disubstituted amines from nitroalkenes
  作者：Mary-Lorène Leroux、Thierry Le Gall、Charles Mioskowski

  DOI：10.1016/s0957-4166(01)00323-8

  日期：2001.7

  Disubstituted nitroalkenes were converted into enantiomerically enriched amines (isolated as their hydrochloride salts) with enantiomeric excesses of 88 to > 95% in three steps: (a) highly stereoselective conjugate addition of the potassium salt of 4-phenyloxazolidin-2-one; (b) radical-mediated removal of the nitro group: (c) cleavage of the oxazolidinone. (C) 2001 Elsevier Science Ltd. All rights reserved.