(Z)-ethyl 3-nitro-2-phenylacrylate | 923271-74-3

• 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)-ethyl 3-nitro-2-phenylacrylate
• 英文别名: ethyl (Z)-3-nitro-2-phenylacrylate；ethyl (Z)-3-nitro-2-phenylprop-2-enoate
• CAS: 923271-74-3
• 化学式: C₁₁H₁₁NO₄
• 分子量: 221.213
• InChiKey: RNIIKTDROOVNRM-NTMALXAHSA-N

物化性质

• 沸点：
  340.9±31.0 °C(Predicted)
• 密度：
  1.208±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

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：

  (Z)-ethyl 3-nitro-2-phenylacrylate 在 Chr-OYE₁ (old yellow enzyme from chryseobacterium sp. CA₄₉) 、 NADH 作用下， 以 aq. phosphate buffer 为溶剂， 反应 0.03h， 以96%的产率得到
  参考文献：
  名称：

  Two “classical” Old Yellow Enzymes from Chryseobacterium sp. CA49: Broad substrate specificity of Chr-OYE1 and limited activity of Chr-OYE2

  摘要：

  Two putative Old Yellow Enzyme (OYE) homologues, Chr-OYE1 and Chr-OYE2, were identified from the genome of Chryseobacterium sp. CA49 as new members of the "classical" subfamily. Chr-OYE1 and Chr-OYE2 were most closely related to the SYE4 from Shewanella oneidensis and NerA from Agrobacterium radiobacter with 41% and 45% identity, respectively. Both enzymes were expressed in Escherichia coli in soluble form, but their catalytic abilities as ene-reductases were quite different. Among the 19 substrate tested, Chr-OYE1 could catalyze the reduction of 18 of them including an ynone with excellent stereos electivity for several prochiral ones, and its specific activity was roughly 1100-fold high than Chr-OYE2, which only catalyzed 3 of the substrates. After restoring the conserved tyrosine, Chr-OYE2 remained the same substrate spectrum, but showed significantly enhanced activity and stereoselectivity. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2015.11.008
• 作为产物：
  描述：

  苯甲酰甲酸乙酯 在 乙酸酐 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 96.0h， 生成 (Z)-ethyl 3-nitro-2-phenylacrylate
  参考文献：
  名称：

  现成的氢键催化剂可用于硝基烯烃的不对称转移氢化†

  摘要：

  本文着重于易于访问的内容 硫脲衍生自氨基酸的氢键催化剂，其位阻和电子特征受其在甲醇碳中心的取代度的调节。这些催化剂被用于硝基烯烃的不对称转移氢化，从而以高达99％的收率和86％的对映体过量提供手性产物。所提出的催化剂的作用方式得到机理研究的支持。

  DOI：

  10.1039/c1ob05059a

文献信息

• Asymmetric Friedel–Crafts Alkylation of α-Substituted β-Nitroacrylates: Access to β^2,2-Amino Acids Bearing Indolic All-Carbon Quaternary Stereocenters
  作者：Jian-Quan Weng、Qiao-Man Deng、Liang Wu、Kai Xu、Hao Wu、Ren-Rong Liu、Jian-Rong Gao、Yi-Xia Jia

  DOI：10.1021/ol403480v

  日期：2014.2.7

  A highly enantioselective Friedel–Crafts alkylation reaction of indoles with acyclic α-substituted β-nitroacrylates is developed under the catalysis of Ni(ClO4)2–bisoxazoline complex at 1 mol % catalyst loading, affording chiral indolic β-nitroesters bearing all-carbon quaternary stereocenters in excellent yields and ees of up to 97%. Transformation of one of the products to β2,2-amino ester and t

  在Ni（ClO 4）2-双恶唑啉配合物的催化下，以1 mol％的负载量催化吲哚与非环状α-取代的β-硝基丙烯酸酯的高度对映选择性Friedel-Crafts烷基化反应，从而得到具有全碳的手性吲哚β-硝基酯四元立体中心，产率极高，ee高达97％。举例说明了其中一种产物通过硝基还原和连续的Pictet-Spengler环化反应转变为β2,2-氨基酯和四氢-β-咔啉。
• Organocatalytic enantioselective Michael reaction of 1,3-dicarbonyls with α-substituted β-nitroacrylates
  作者：Hsuan-Hao Chang、Kai-Ti Chu、Ming-Hsi Chiang、Jeng-Liang Han

  DOI：10.1016/j.tet.2016.12.039

  日期：2017.2

  An efficient asymmetric Michael reaction of 1,3-dicarbonyl compounds with α-Substituted-β-Nitroacrylates has been developed by using a cinchona-thiourea bifunctional organocatalyst in high yields and enantioselectivies. One of adducts could be transformed into a chiral β-nitroester bearing an isoxazole skeleton and an all-carbon quaternary chiral center.

  通过使用金鸡纳-硫脲双功能有机催化剂，已高收率和对映选择性地开发了1,3-二羰基化合物与α-取代的-β-硝基丙烯酸酯的有效不对称迈克尔反应。一种加合物可以转变为带有异恶唑骨架和全碳季手性中心的手性β-硝基酯。
• The Friedel–Crafts Reaction of Indoles with Michael Acceptors Catalyzed by Magnesium and Calcium Salts
  作者：Irina Beletskaya、Mikhail Feofanov、Maxim Anokhin、Alexei Averin

  DOI：10.1055/s-0036-1589068

  日期：2017.11

  the addition to various unsaturated carbonyl compounds, while calcium triflimide [Ca(NTf2)2] efficiently catalyzed the addition to nitroolefins. Friedel–Crafts alkylation of indole and its derivatives with a variety of electron-deficient alkenes catalyzed by Mg and Ca salts has been studied. The dependence of the results on the nature of the starting olefins, substituents on indole, and Michael acceptors

  摘要 已经研究了Mg和Ca盐催化的吲哚及其衍生物与多种电子缺陷的烯烃的Friedel-Crafts烷基化反应。讨论了结果对起始烯烃的性质，吲哚和迈克尔受体上的取代基以及路易斯酸的组成的依赖性。将吲哚添加到β，γ-不饱和α-酮酸酯和香豆素衍生物，一些硝基烯烃和芳基丙二酸酯中可实现高收率的加成产物。发现涉及芳基丙二酸酯的反应是最通用和最平滑的，最高收率达到92％。在所测试的Mg和Ca盐中，除了各种不饱和羰基化合物外，碘化镁（MgI 2）被证明是最合适的催化剂，而三氟甲磺酸钙[Ca（NTf2）2 ]有效地催化了向硝基烯烃的加成。 已经研究了Mg和Ca盐催化的吲哚及其衍生物与多种电子缺陷的烯烃的Friedel-Crafts烷基化反应。讨论了结果对起始烯烃的性质，吲哚和迈克尔受体上的取代基以及路易斯酸的组成的依赖性。将吲哚添加到β，γ-不饱和α-酮酸酯和香豆素衍生物，一些硝基烯烃和芳基丙二酸酯中可实
• Peptide-Catalyzed Stereoselective Conjugate Addition Reactions Generating All-Carbon Quaternary Stereogenic Centers
  作者：Robert Kastl、Helma Wennemers

  DOI：10.1002/anie.201301583

  日期：2013.7.8

  A powerful catalyst: Quaternary stereogenic centers adjacent to tertiary stereocenters were formed with high diastereoselectivities and enantioselectivities in conjugate addition reactions between aldehydes and β,β‐disubstituted nitroolefins by using a peptidic catalyst (see scheme). γ‐Amino acids and heterocyclic compounds bearing quaternary stereogenic centers are easily accessible from the products

  强大的催化剂：在醛与β，β-二取代的硝基烯烃之间通过肽类催化剂进行共轭加成反应时，与叔立体中心相邻的四级立体中心具有很高的非对映选择性和对映选择性（请参见方案）。容易从产品中获得带有季立体中心的γ-氨基酸和杂环化合物。
• Syn-selective nitro-Michael addition of furanones to β,β-disubstituted nitroalkenes catalyzed by epi-quinine derivatives
  作者：Tohru Sekikawa、Hayato Kitaura、Takayuki Kitaguchi、Tatsuya Minami、Yasuo Hatanaka

  DOI：10.1016/j.tetlet.2016.05.093

  日期：2016.7

  Epi-quinine-catalyzed asymmetric nitro-Michael addition of furanones to β,β,-disubstituted nitroalkenes is described. The reaction proceeded smoothly with 1–5 mol % loadings of epi-quinine catalysts at room temperature, giving the corresponding Michael adducts in high yields (72–93%) with extremely high diastereo- and enantioselectivities (>98/2 dr, syn major; 95–99% ee). This reaction provides an

  外延-quinine催化不对称硝基迈克尔加成呋喃酮的对β，β，α-二取代的硝基烯烃进行说明。该反应用的1-5摩尔％的负载量顺利外延在室温下-quinine催化剂，以高收率（72-93％）具有极高diastereo-和对映选择性（> 98/2博士，得到相应的迈克尔加成物的顺式大; 95–99％ee）。该反应提供了一种有效且直接的方法，用于构建与含氧季立体中心相邻的全碳季立体中心。