(2E)-3-(3-硝基苯基)丙烯酰胺 | 130973-09-0

• 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: (2E)-3-(3-硝基苯基)丙烯酰胺
• 英文名称: (E)-3-(3-nitrophenyl)acrylamide
• 英文别名: (E)-3-nitrocinnamamide；m-nitrocinnamide；3-nitro-trans-cinnamic acid amide；3-Nitro-trans-zimtsaeure-amid；(E)-3-(3-nitrophenyl)prop-2-enamide
• CAS: 130973-09-0
• 化学式: C₉H₈N₂O₃
• mdl: MFCD00705371
• 分子量: 192.174
• InChiKey: QDGXIICOKBFSQX-SNAWJCMRSA-N

物化性质

• 熔点：
  194-195 °C
• 沸点：
  438.9±45.0 °C(Predicted)
• 密度：
  1.343±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  88.9
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  (2E)-3-(3-硝基苯基)丙烯酰胺 在 劳森试剂 、 乙醇 、 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 生成 (E)-3-[2-[4-(1-methylethyl)-2-thiazolyl]ethenyl]benzeneamine
  参考文献：
  名称：

  MexAB-OprM-Specific efflux pump inhibitors in Pseudomonas aeruginosa. Part 1: Discovery and early strategies for lead optimization

  摘要：

  The identification of a series of compounds that specifically inhibit efflux by the MexAB-OprM pump system in Pseudomonas aeruginosa is described. Synthesis and in vitro structure-activity relationships (SARs) are outlined. Early leads lacked activity in animal models, and efforts to improve solubility and reduce serum protein binding by the introduction of polar groups are discussed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.07.024
• 作为产物：
  描述：

  3-硝基肉桂酸 在 氯化亚砜 、 氨 作用下， 生成 (2E)-3-(3-硝基苯基)丙烯酰胺
  参考文献：
  名称：

  MexAB-OprM-Specific efflux pump inhibitors in Pseudomonas aeruginosa. Part 1: Discovery and early strategies for lead optimization

  摘要：

  The identification of a series of compounds that specifically inhibit efflux by the MexAB-OprM pump system in Pseudomonas aeruginosa is described. Synthesis and in vitro structure-activity relationships (SARs) are outlined. Early leads lacked activity in animal models, and efforts to improve solubility and reduce serum protein binding by the introduction of polar groups are discussed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.07.024

文献信息

• A Facile Approach to Arylacetaldehydes via Polymeric Palladium Catalyst
  作者：Zhang Zhuangyu、Pan Yi、Hu Honwen、Kao Tsi-yu

  DOI：10.1055/s-1991-26512

  日期：——

  Several arylacetaldehydes 5 were synthesized in moderate yields via Heck reaction of acrylamide (1) with substituted iodobenzenes 2 in the presence of the polymeric catalyst -phenyl-(1,10-phenanthroline)-palladium(0) [-ph-phen.Pd(0)] followed by Hofmann reaction and subsequent hydrolysis.

  通过在聚合催化剂-苯基-(1，10-菲咯啉)-钯(0)存在下的烯酰胺(1)与取代碘苯(2)的Heck反应，合成了中等产率的若干种芳基乙醛(5)，随后进行Hofmann反应和后续的水解处理。
• Binaphthyl-bridged bis-imidazolinium salts as N-heterocyclic carbene ligand precursors in the palladium-catalyzed Heck reaction
  作者：Hui Wu、Can Jin、GuoLi Huang、LianJun Wang、JuLi Jiang、LeYong Wang

  DOI：10.1007/s11426-011-4272-4

  日期：2011.6

  Two new bis-imidazolinium salts (4a, 4b) have been synthesized as precursors of N-heterocyclic carbenes (NHCs) from the commercially available (R)-2,2′-dihydroxy-1,1′-binaphthalene. The two bis-imidazolinium salts were used as efficient precursor of NHC ancillary ligands in the palladium-catalyzed Heck reaction. Good to excellent yields and high stereoselectivities were obtained with ethyl acrylate, acrylonitrile, and acrylamide as starting materials. The structure of bis-imidazolinium salt 4b was further characterized by single crystal X-ray diffraction analysis.

  两种新的双咪唑铵盐（4a，4b）作为N-杂环氮烯（NHC）的前体已合成，这些材料来源于商业可得的（R）-2,2′-二羟基-1,1′-联萘。这两种双咪唑铵盐在钯催化的Heck反应中作为NHC辅助配体的高效前体。使用乙基丙烯酸酯、丙烯腈和丙烯酰胺作为起始材料时，获得了良好至优异的产率和高选择性。双咪唑铵盐4b的结构进一步通过单晶X射线衍射分析进行了表征。
• Ce(III) immobilised on aminated epichlorohydrin-activated agarose matrix – “green” and efficient catalyst for transamidation of carboxamides
  作者：Zeinab Zarei、Batool Akhlaghinia

  DOI：10.1515/chempap-2015-0168

  日期：2015.1.1

  “green” catalyst. The catalyst was synthesised by the reaction of the epichlorohydrin-activated agarose matrix with ammonia solution, which was then treated with Ce(NO3)3 · 6H2O. The catalyst (CAEA) was characterised by FT-IR, far IR, CHN, XRD, TGA, and ICP techniques. CAEA is shown to be an effective and reusable heterogeneous catalyst for the transamidation of carboxamides with amines under solvent-free

  本研究报告了固定化在胺化表氯醇活化的琼脂糖基质（CAEA）上的Ce（III）作为“绿色”催化剂的制备和表征。通过表氯醇活化的琼脂糖基质与氨溶液反应合成催化剂，然后用Ce（NO 3）3 ·6H 2处理O.催化剂（CAEA）通过FT-IR，远红外，CHN，XRD，TGA和ICP技术表征。已证明，CAEA是在无溶剂条件下将羧酰胺与胺进行氨基转移的有效且可重复使用的多相催化剂。该催化剂已成功地用于合成多种芳香族和脂肪族酰胺。高效，温和的反应条件，易于处理，简单的分离以及可重复使用性是该催化剂的重要优点。
• Selective and facile synthesis of α,β-unsaturated nitriles and amides with N-hydroxyphthalimide as the nitrogen source
  作者：Yiyan Yan、Xiaohe Xu、Xiaokang Jie、Jingya Cheng、Renren Bai、Qi Shuai、Yuanyuan Xie

  DOI：10.1016/j.tetlet.2018.06.011

  日期：2018.7

  The direct conversion of α,β-unsaturated aldehydes to corresponding nitriles promoted by Pd(OAc)2 and phthalic acid which was hydrolyzed from N-hydroxyphthalimide (NHPI) has been disclosed. Additionally, it was found that when water was used as the solvent, α,β-unsaturated amides was obtained as the main products in good to excellent yields. It was first reported that NHPI was utilized as the nitrogen

  已经公开了由N-羟基邻苯二甲酰亚胺（NHPI）水解的Pd（OAc）2和邻苯二甲酸促进的α，β-不饱和醛直接转化为相应的腈。另外，发现当使用水作为溶剂时，以良好至优异的产率获得α，β-不饱和酰胺作为主要产物。首次报道，NHPI被用作氮源，由醛合成α，β-不饱和腈和酰胺。对照实验表明，醛经过肟化和脱水过程形成腈和酰胺。
• Novel photocatalytic product from m-nitrocinnamic acid and alcohol mediated by TiO2
  作者：Koon Ha Park、Hyun Sang Joo、Sung Won Kim、Myeong Soon Park、Pill Soo Shin、Kun Jun、Kyung Il Ahn

  DOI：10.1016/s0040-4039(98)02549-0

  日期：1999.2

  skeleton of 7-membered lactone and a 1,2,3,4-tetrahydroquinoline were obtained from TiO2 suspended alcoholic solution of trans m-nitrocinnamic acid 4 by uv (350 nm) irradiation. Highly functionalized products 6 are believed to be formed through 4-alkoxy-1,2,3,4-tetrahydroquinolines 5.

  通过UV（350nm）照射从反式间硝基肉桂酸4的TiO 2悬浮的醇溶液中获得具有7元内酯和1,2,3,4-四氢喹啉骨架的新杂环6。认为高度官能化的产物6是通过4-烷氧基-1,2,3,4-四氢喹啉5形成的。