(Z)-ethyl 3-nitro-3-phenylacrylate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-ethyl 3-nitro-3-phenylacrylate
• 英文别名: ethyl (Z)-3-nitro-3-phenylprop-2-enoate
• 化学式: C₁₁H₁₁NO₄
• 分子量: 221.213
• InChiKey: AQYUKJJXFJAXIT-NTMALXAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酰乙酸乙酯 、 (Z)-ethyl 3-nitro-3-phenylacrylate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 2-[1-Hydroxy-eth-(Z)-ylidene]-3-[1-phenyl-meth-(E)-ylidene]-succinic acid diethyl ester
  参考文献：
  名称：

  β-Nitro acrylic esters as precursors for the one pot synthesis of polyfunctionalized α,β-unsaturated esters

  摘要：

  Conjugate addition of activated methylene derivatives to beta-nitro acrylic esters in acetonitrile with DBU (2 equiv) as base, allows the one pot formation of polyfunctionalized alpha,beta-unsaturated esters. The procedure is based on a tandem 'Michael addition elimination' process favoured by the Simultaneous behaviour of the nitro group as both an electron-withdrawing and leaving group. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.01.009
• 作为产物：
  描述：

  反式-肉桂酸乙酯 在 ammonium cerium(IV) nitrate 、 sodium nitrite 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 (E)-ethyl 3-nitro-3-phenylacrylate 、 (Z)-ethyl 3-nitro-3-phenylacrylate
  参考文献：
  名称：

  NaNO 2-硝酸硝酸铈介导的丙烯酸酯和Baylis-Hillman衍生的丙烯酸酯向相应的β-硝基丙烯酸酯的转化

  摘要：

  各种丙烯酸酯，包括那些由Baylis-Hillman反应衍生的丙烯酸酯，与NaNO 2-铈硝酸铵反应生成相应的β-硝基醇2和5，它们通过甲磺酸酯的脱水作用，生成β-硝基丙烯酸酯。好到极好的产量。此外，从Baylis-Hillman产品获得的含有甲磺酸酯基团6的β-硝基丙烯酸酯与NaN 3反应，以极好的收率形成2-氰基-3-取代的丙烯酸酯10。

  DOI：

  10.1016/j.tet.2003.11.013

文献信息

• An unusual contra-Michael addition of NaNO2–ceric ammonium nitrate to acrylic esters
  作者：Alexei V. Buevich、Yusheng Wu、Tze-Ming Chan、Andrew Stamford

  DOI：10.1016/j.tetlet.2008.01.123

  日期：2008.3

  This report describes a novel regioselective contra-Michael addition to cinnamic esters that utilizes NaNO2–ceric ammonium nitrate.

  该报告描述了利用NaNO 2-硝酸硝酸铵在肉桂酸酯上的一种新的区域选择性对-迈克尔加成反应。
• Addition of thionucleophiles to nitrocinnamates: approach toward synthesis of (alkyl/aryl)thio-amino acids
  作者：Elzbieta Lewandowska

  DOI：10.1080/17415993.2015.1107726

  日期：2016.3.3

  The addition of alkyl or aryl thiols to alpha-nitro or beta-nitrocinnamate in the presence of base provided Michael addition products. In the case of beta-nitro compounds reaction occurred via the formation of anti-Michael adducts. Selective nitro reduction of alpha-nitroadducts gives access to beta-thio-alpha-amino acid derivatives.
• SHIN C.; KOSUGE Y.; YAMAURA M.; YOSHIMURA J., BULL. CHEM. SOC. JAP., 1978, 51, NO 4, 1137-1141
  作者：SHIN C.、 KOSUGE Y.、 YAMAURA M.、 YOSHIMURA J.

  DOI：——

  日期：——
• NaNO2–Ceric ammonium nitrate mediated conversion of acrylic esters and Baylis–Hillman derived acrylic esters into corresponding β-nitro acrylic esters
  作者：K Jayakanthan、K.P Madhusudanan、Yashwant D Vankar

  DOI：10.1016/j.tet.2003.11.013

  日期：2004.1

  A variety of acrylic esters, including those derived from Baylis–Hillman reactions, react with NaNO2–ceric ammonium nitrate to form the corresponding β-nitro alcohols 2 and 5 whose dehydration, via their mesylates, leads to β-nitro acrylic esters, in good to excellent yields. Further, β-nitro acrylic esters containing a mesylate group 6, obtained from the Baylis–Hillman products, react with NaN3 to

  各种丙烯酸酯，包括那些由Baylis-Hillman反应衍生的丙烯酸酯，与NaNO 2-铈硝酸铵反应生成相应的β-硝基醇2和5，它们通过甲磺酸酯的脱水作用，生成β-硝基丙烯酸酯。好到极好的产量。此外，从Baylis-Hillman产品获得的含有甲磺酸酯基团6的β-硝基丙烯酸酯与NaN 3反应，以极好的收率形成2-氰基-3-取代的丙烯酸酯10。
• β-Nitro acrylic esters as precursors for the one pot synthesis of polyfunctionalized α,β-unsaturated esters
  作者：Roberto Ballini、Dennis Fiorini、Alessandro Palmieri

  DOI：10.1016/j.tetlet.2005.01.009

  日期：2005.2

  Conjugate addition of activated methylene derivatives to beta-nitro acrylic esters in acetonitrile with DBU (2 equiv) as base, allows the one pot formation of polyfunctionalized alpha,beta-unsaturated esters. The procedure is based on a tandem 'Michael addition elimination' process favoured by the Simultaneous behaviour of the nitro group as both an electron-withdrawing and leaving group. (C) 2005 Elsevier Ltd. All rights reserved.