Z-ethyl α-nitro-β-(4-nitrophenyl)acrylate | 78324-35-3

• 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 α-nitro-β-(4-nitrophenyl)acrylate
• 英文别名: ethyl (Z)-2-nitro-3-(4-nitrophenyl)propenoate；ethyl (Z)-2-nitro-3-(4-nitrophenyl)acrylate；ethyl 2-nitro-3-(4-nitrophenyl)propenoate；4,α-dinitro-trans-cinnamic acid ethyl ester；4,α-Dinitro-trans-zimtsaeure-aethylester；1-Nitro-2-(4-nitrophenyl)-1-ethoxy-carbonylethene；ethyl (Z)-2-nitro-3-(4-nitrophenyl)prop-2-enoate
• CAS: 78324-35-3
• 化学式: C₁₁H₁₀N₂O₆
• 分子量: 266.21
• InChiKey: NFBZDSNHBGQYBK-YFHOEESVSA-N

物化性质

• 沸点：
  391.3±32.0 °C(Predicted)
• 密度：
  1.391±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 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：
  118
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Z-ethyl α-nitro-β-(4-nitrophenyl)acrylate 以 氘代甲醇 为溶剂， 反应 0.12h， 生成
  参考文献：
  名称：

  1 H NMR光谱法研究β-芳基（杂芳基）-α-硝基丙烯酸乙酯的几何异构

  摘要：

  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。

  DOI：

  10.1134/s1070363216010102
• 作为产物：
  描述：

  硝基乙酸乙酯 、 N-(4-硝基苯基亚甲基)-正丁胺 在 乙酸酐 作用下， 生成 Z-ethyl α-nitro-β-(4-nitrophenyl)acrylate
  参考文献：
  名称：

  Dornow; Menzel, Justus Liebigs Annalen der Chemie, 1954, vol. 588, p. 40,44

  摘要：

  DOI：

文献信息

• Domino reactions for the synthesis of various α-substituted nitro alkenes
  作者：Stefania Fioravanti、Lucio Pellacani、Maria Cecilia Vergari

  DOI：10.1039/c1ob06260c

  日期：——

  Efficient one-pot methods for the synthesis of variously functionalised conjugated nitro alkenes have been reported. Despite the utility in different fields of these compounds, only a few multi-step syntheses have been reported in the literature, giving the target compounds in low overall yields. α-Nitro acrylates or cinnamates, α-nitro α,β-unsaturated ketones and, most importantly, aromatic and heteroaromatic

  已经报道了用于合成各种官能化的共轭硝基烯烃的有效的一锅法。尽管这些化合物在不同领域有实用性，但文献中仅报道了几步合成，以较低的总收率得到了目标化合物。以高收率获得了α-硝基丙烯酸酯或肉桂酸酯，α-硝基α，β-不饱和酮，以及最重要的是芳香族和杂芳香族（E）-2-硝基烯丙醇，这些化合物具有众所周知的抗癌活性。通过多米诺骨牌缩合脱水过程获得高非对映异构体纯度。
• The synthesis of highly functionalized seven-membered allyl ethers using palladium-catalyzed alkoxyallylation of activated olefins and ring-closing olefin metathesis
  作者：Roger L Xie、James R Hauske

  DOI：10.1016/s0040-4039(00)01834-7

  日期：2000.12

  The investigation of palladium-catalyzed alkoxyallylation of activated olefins, followed by ring-closing metathesis to synthesize functionalized seven-membered ring allyl ethers is described. The influence of the olefin substituents on the diastereoselectivity of the alkoxyallylation has also been examined.

  描述了钯催化活化烯烃的烷氧基化反应，然后进行闭环复分解以合成官能化的七元环烯丙基醚的研究。还研究了烯烃取代基对烷氧基烯丙基化的非对映选择性的影响。
• Moodie, Roy B.; Schofield, Kenneth; Taylor, Peter G., Journal of the Chemical Society. Perkin transactions II, 1981, p. 842 - 847
  作者：Moodie, Roy B.、Schofield, Kenneth、Taylor, Peter G.、Baillie, Philip J.

  DOI：——

  日期：——
• Selective Amination Reactions of α-Nitro Aryl and Heteroaryl Enoates
  作者：Stefania Fioravanti、Lucio Pellacani、Maria Cecilia Vergari

  DOI：10.1021/jo4012859

  日期：2013.8.16

  Highly functionalized tetrasubstituted alkenes were obtained by an unexpected amination reaction promoted by ethyl nosyloxycarbamate on various alpha-nitro aryl and heteroaryl enoates. A nitrene is likely the aminating species responsible for the observed insertion reaction leading to (E)-beta-amino alpha-nitro enoates as the major products, regardless of the substrate configuration. The compounds, bearing two nitrogenous functional groups in different oxidation states, can be regarded as interesting synthons. In contrast, aziridination was observed for alpha-nitro alkyl enoates or beta-nitro allylic alcohols.
• 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.