(Z)-3-phenyl-2-nitro-2-butene | 91923-49-8

• 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: (Z)-3-phenyl-2-nitro-2-butene
• 英文别名: (1-Methyl-2-nitro-1-propen-1-yl)-benzene；[(Z)-3-nitrobut-2-en-2-yl]benzene
• CAS: 91923-49-8
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: SMLHUHINFZJSHO-HJWRWDBZSA-N

物化性质

• 沸点：
  114 °C(Press: 20 Torr)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  (Z)-3-phenyl-2-nitro-2-butene 在 palladium on activated charcoal 氢气 作用下， 以 乙醚 为溶剂， 反应 6.0h， 以72%的产率得到(+/-)-erythro-3-phenyl-2-nitrobutane
  参考文献：
  名称：

  Asymmetric reduction of nitroalkenes with baker's yeast

  摘要：

  Various alpha,beta -disubstituted and trisubstituted nitroalkenes were chemoselectively reduced with baker's yeast to the corresponding nitroalkanes. Stereoselectivities of the reduction of alpha,beta -disubstituted nitroalkenes were modest to low, and e.e.s up to 52% were obtained. Trisubstituted nitroalkenes could be reduced to the corresponding nitroalkanes with excellent enantioselectivities, moderate diastereoselectivities and in good yield. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00029-5
• 作为产物：
  描述：

  2-苯-2-丁烯 在 硫酸 、 硝酸 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 0.33h， 生成 (Z)-3-phenyl-2-nitro-2-butene
  参考文献：
  名称：

  Asymmetric reduction of nitroalkenes with baker's yeast

  摘要：

  Various alpha,beta -disubstituted and trisubstituted nitroalkenes were chemoselectively reduced with baker's yeast to the corresponding nitroalkanes. Stereoselectivities of the reduction of alpha,beta -disubstituted nitroalkenes were modest to low, and e.e.s up to 52% were obtained. Trisubstituted nitroalkenes could be reduced to the corresponding nitroalkanes with excellent enantioselectivities, moderate diastereoselectivities and in good yield. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00029-5

文献信息

• Stereochemical Outcome of the Biocatalysed Reduction of Activated Tetrasubstituted Olefins by Old Yellow Enzymes 1–3
  作者：Elisabetta Brenna、Francesco G. Gatti、Daniela Monti、Fabio Parmeggiani、Stefano Serra

  DOI：10.1002/adsc.201100504

  日期：2012.1

  old yellow enzymes (OYEs) 1–3. The comprehension of the resulting data required a careful analysis of the stereochemical course of this kind of reaction. The investigation of the bioreduction of tetrasubstituted alkenes allowed us to appreciate the contribution of several factors (configuration of the starting alkene, mechanism of hydrogen addition, substrate binding mode) to the overall stereochemistry

  四取代活化烯烃的（E）和（Z）立体异构体的烯还原酶介导的反应是通过分离的旧黄色酶（OYEs）1-3进行的。对所得数据的理解需要仔细分析这种反应的立体化学过程。对四取代烯烃的生物还原的研究使我们认识到几个因素（起始烯烃的构型，氢加成的机理，底物结合模式）对反应的整体立体化学的贡献。
• Asymmetric synthesis of a nitroalkane by the use of novel nitroalkene reductases from baker's yeast
  作者：Yasushi Kawai、Yoshikazu Inaba、Motoko Hayashi、Norihiro Tokitoh

  DOI：10.1016/s0040-4039(01)00464-6

  日期：2001.5

  Two kinds of novel nitroalkene reductases were isolated from baker's yeast. Reduction of a trisubstituted nitroalkene by these reductases afforded the corresponding nitroalkane with excellent enantioselectivity, moderate diastereoselectivity, and in good yield.

  从面包酵母中分离出两种新型的硝基烯还原酶。通过这些还原酶还原三取代的硝基烯烃，得到相应的硝基烷，其具有优异的对映选择性，适度的非对映选择性和良好的收率。
• Grant, Richard D.; Pinhey, John T., Australian Journal of Chemistry, 1984, vol. 37, # 6, p. 1231 - 1244
  作者：Grant, Richard D.、Pinhey, John T.

  DOI：——

  日期：——
• GRANT, R. D.;PINHEY, J. T., AUSTRAL. J. CHEM., 1984, 37, N 6, 1231-1244
  作者：GRANT, R. D.、PINHEY, J. T.

  DOI：——

  日期：——
• Asymmetric reduction of nitroalkenes with baker's yeast
  作者：Yasushi Kawai、Yoshikazu Inaba、Norihiro Tokitoh

  DOI：10.1016/s0957-4166(01)00029-5

  日期：2001.2

  Various alpha,beta -disubstituted and trisubstituted nitroalkenes were chemoselectively reduced with baker's yeast to the corresponding nitroalkanes. Stereoselectivities of the reduction of alpha,beta -disubstituted nitroalkenes were modest to low, and e.e.s up to 52% were obtained. Trisubstituted nitroalkenes could be reduced to the corresponding nitroalkanes with excellent enantioselectivities, moderate diastereoselectivities and in good yield. (C) 2001 Elsevier Science Ltd. All rights reserved.