3-(4-氯苯基)-2-硝基-2-烯酸乙酯 | 60859-80-5

• 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
• 中文名称: 3-(4-氯苯基)-2-硝基-2-烯酸乙酯
• 英文名称: ethyl (Z)-3-(4-chlorophenyl)-2-nitropropenoate
• 英文别名: (Z)-ethyl 3-(4-chlorophenyl)-2-nitroacrylate；ethyl 3-(4-chlorophenyl)-2-nitropropenoate；4-chloro-α-nitro-trans-cinnamic acid ethyl ester；4-Chlor-α-nitro-trans-zimtsaeure-aethylester；ethyl (Z)-3-(4-chlorophenyl)-2-nitroprop-2-enoate
• CAS: 60859-80-5
• 化学式: C₁₁H₁₀ClNO₄
• 分子量: 255.658
• InChiKey: KFPZCHSGHBGUPC-YFHOEESVSA-N

物化性质

• 沸点：
  373.5±32.0 °C(Predicted)
• 密度：
  1.335±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 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：

  3-(4-氯苯基)-2-硝基-2-烯酸乙酯 在 盐酸 、 copper(II) bis(trifluoromethanesulfonate) 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 99.0h， 生成
  参考文献：
  名称：

  硝基丙烯酸酯催化吲哚的不对称弗里德-克拉夫茨烷基化反应。在色氨酸类似物合成中的应用

  摘要：

  已开发出手性（4 R，5 S）-DiPh-BOX（L1）-Cu（OTf）2络合物（10 mol％）催化的吲哚与硝基丙烯酸酯的吲哚不对称弗里德-克拉夫茨烷基化反应。该反应以中等非对映选择性提供色氨酸硝基前体（抗/合成至72:28），对映选择性良好（至99％ee）。烷基化产物可以很容易地还原为具有Zn / H +的旋光色氨酸类似物。

  DOI：

  10.1016/j.tet.2007.03.175
• 作为产物：
  描述：

  4-氯苯甲醛 在 乙酸酐 、 magnesium sulfate 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 生成 3-(4-氯苯基)-2-硝基-2-烯酸乙酯
  参考文献：
  名称：

  Asymmetric Friedel–Crafts alkylation of indoles with 2-nitro-3-arylacrylates catalyzed by a metal-templated hydrogen bonding catalyst

  摘要：

  An asymmetric Friedel-Crafts alkylation of indoles with 2-nitro-3-arylacrylates catalyzed by a metal-templated hydrogen bonding catalyst has been established. The asymmetric induction relies on chirality transfer solely from the octahedral metal stereocenter via three weak hydrogen bonds. All the products are provided with good to excellent enantioselectivities while modest diastereoselectivities, which can be converted into a variety of valuable indole-containing chiral building blocks including tryptophan derivatives. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.06.046

文献信息

• Study of geometric isomerism of ethyl β-aryl(hetaryl)-α-nitroacrylates by 1H NMR spectroscopy method
  作者：R. I. Baichurin、D. B. Berestovitskaya、L. V. Baichurina、N. I. Aboskalova、V. M. Berestovitskaya

  DOI：10.1134/s1070363216010102

  日期：2016.1

  furyl and thienyl heteroanalogs depending on the nature of the substituent in the β-position of α-nitroacrylates, deuterated solvent and duration of exposure of the sample were studied by means of 1H NMR spectroscopy.

  根据α-硝基丙烯酸酯的β位上取代基的性质，氘代溶剂和样品的暴露时间，研究了α-硝基肉桂酸乙酯的Z → E异构化及其呋喃基和噻吩基杂类似物的特征。1 H NMR光谱。
• Synthesis and structure of β-aryl-α-nitroacrylates
  作者：R. I. Baichurin、L. V. Baichurina、N. I. Aboskalova、V. M. Berestovitskaya

  DOI：10.1134/s1070363213090223

  日期：2013.9

  The method for preparation of ethyl alpha-nitrocinnamates by nitroacetic acid ester alkenylation with aromatic aldehydes in the presence of acetic acid and beta-alanine has been modified. Structures of the prepared compounds have been proved by electronic, IR, H-1, and C-13-H-1} NMR spectroscopy (including heteronuclear correlation experiments H-1-C-13 HMQC and H-1-C-13 HMBC). In solution these compounds exist in the form of Z-isomer; the Za double dagger"E isomerization is observed in the case of the compound containing strong electron-donor group [N(CH3)(2)] at benzene ring.
• Dornow; Menzel, Justus Liebigs Annalen der Chemie, 1954, vol. 588, p. 4043
  作者：Dornow、Menzel

  DOI：——

  日期：——
• Asymmetric Friedel–Crafts alkylation of indoles with 2-nitro-3-arylacrylates catalyzed by a metal-templated hydrogen bonding catalyst
  作者：Jingfen Liu、Lei Gong、Eric Meggers

  DOI：10.1016/j.tetlet.2015.06.046

  日期：2015.8

  An asymmetric Friedel-Crafts alkylation of indoles with 2-nitro-3-arylacrylates catalyzed by a metal-templated hydrogen bonding catalyst has been established. The asymmetric induction relies on chirality transfer solely from the octahedral metal stereocenter via three weak hydrogen bonds. All the products are provided with good to excellent enantioselectivities while modest diastereoselectivities, which can be converted into a variety of valuable indole-containing chiral building blocks including tryptophan derivatives. (C) 2015 Elsevier Ltd. All rights reserved.
• Catalytic and asymmetric Friedel–Crafts alkylation of indoles with nitroacrylates. Application to the synthesis of tryptophan analogues
  作者：Yong Sui、Li Liu、Jun-Ling Zhao、Dong Wang、Yong-Jun Chen

  DOI：10.1016/j.tet.2007.03.175

  日期：2007.6

  An asymmetric Friedel–Crafts alkylation of indoles with nitroacrylates catalyzed by chiral (4R,5S)-DiPh-BOX (L1)–Cu(OTf)2 complex (10 mol %) has been developed. The reactions provide tryptophan nitro-precursors in moderate diastereoselectivities (anti/syn up to 72:28) and good to excellent enantioselectivities (up to 99% ee). The alkylation products could be easily reduced to optically active tryptophan

  已开发出手性（4 R，5 S）-DiPh-BOX（L1）-Cu（OTf）2络合物（10 mol％）催化的吲哚与硝基丙烯酸酯的吲哚不对称弗里德-克拉夫茨烷基化反应。该反应以中等非对映选择性提供色氨酸硝基前体（抗/合成至72:28），对映选择性良好（至99％ee）。烷基化产物可以很容易地还原为具有Zn / H +的旋光色氨酸类似物。