3-(4-硝基苯基)丙-2-烯酰胺 | 20069-71-0

• 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: 3-(4-硝基苯基)丙-2-烯酰胺
• 英文名称: (E)-3-(4-nitrophenyl)acrylamide
• 英文别名: (E)-4-nitrocinnamamide；(2e)-3-(4-Nitrophenyl)acrylamide；(E)-3-(4-nitrophenyl)prop-2-enamide
• CAS: 20069-71-0
• 化学式: C₉H₈N₂O₃
• mdl: MFCD03638186
• 分子量: 192.174
• InChiKey: OAAPPUXSAOJJCV-ZZXKWVIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 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

反应信息

• 作为反应物：
  描述：

  3-(4-硝基苯基)丙-2-烯酰胺 在 五氯化磷 、 iron(II) chloride 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 生成 (E)-3-(4-aminophenyl)-N-[2,2,2-trichloro-1-(pyridin-2-ylcarbamothioylamino)ethyl]prop-2-enamide
  参考文献：
  名称：

  Structure–activity relationship studies of salubrinal lead to its active biotinylated derivative

  摘要：

  The synthesis and structure-activity relationships (SAR) of salubrinal, a small molecule that protects cells from apoptosis induced by endoplasmic reticulum (ER) stress, are described. It is revealed that the trichloromethyl group greatly contributes to the activity. Based on the SAR results, salubrinal was converted into a biotinylated derivative which retains activity and can be used as a biological tool for target identification. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.120
• 作为产物：
  描述：

  对硝基肉桂酸 在 ammonium cerium(IV) nitrate 、 尿素 作用下， 反应 0.02h， 以92%的产率得到3-(4-硝基苯基)丙-2-烯酰胺
  参考文献：
  名称：

  Reddy, Ch. Sanjeeva; Raghu; Nagaraj, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2008, vol. 47, # 2, p. 315 - 318

  摘要：

  DOI：

文献信息

• Molecules having pesticidal utility, and intermediates, compositions, and processes, related thereto
  申请人：Dow AgroSciences LLC

  公开号：US20170064962A1

  公开（公告）日：2017-03-09

  This disclosure relates to the field of molecules having pesticidal utility against pests in Phyla Arthropoda, Mollusca, and Nematoda, processes to produce such molecules, intermediates used in such processes, pesticidal compositions containing such molecules, and processes of using such pesticidal compositions against such pests. These pesticidal compositions may be used, for example, as acaricides, insecticides, miticides, molluscicides, and nematicides. This document discloses molecules having the following formula (“Formula One”).

  这份披露涉及具有对节肢动物门、软体动物门和线虫门害虫有用的杀虫性的分子领域，用于生产这种分子的过程，用于这种过程的中间体，含有这种分子的杀虫组合物，以及使用这种杀虫组合物对这些害虫进行处理的过程。这些杀虫组合物可以用作螨虫剂、杀虫剂、螨虫剂、软体动物杀虫剂和线虫杀虫剂。本文件披露了具有以下式（“式一”）的分子。
• Optimization and Evaluation of 5-Styryl-Oxathiazol-2-one<i>Mycobacterium tuberculosis</i>Proteasome Inhibitors as Potential Antitubercular Agents
  作者：Francesco Russo、Johan Gising、Linda Åkerbladh、Annette K. Roos、Agata Naworyta、Sherry L. Mowbray、Anders Sokolowski、Ian Henderson、Torey Alling、Mai A. Bailey、Megan Files、Tanya Parish、Anders Karlén、Mats Larhed

  DOI：10.1002/open.201500001

  日期：2015.6

  5‐styryl‐oxathiazol‐2‐ones as inhibitors of the Mycobacterium tuberculosis (Mtb) proteasome. As part of the study, the structure–activity relationship of oxathiazolones as Mtb proteasome inhibitors has been investigated. Furthermore, the prepared compounds displayed a good selectivity profile for Mtb compared to the human proteasome. The 5‐styryl‐oxathiazol‐2‐one inhibitors identified showed little activity

  这是5-苯乙烯基草并恶唑-2-酮类药物作为结核分枝杆菌（Mtb）蛋白酶体抑制剂的首次报道。作为研究的一部分，已研究了草硫唑酮作为Mtb蛋白酶体抑制剂的构效关系。此外，与人蛋白酶体相比，制备的化合物对Mtb表现出良好的选择性。鉴定出的5-styryl-oxathiazol-2-one抑制剂对复制Mtb几乎没有活性，但对非复制细菌具有快速杀菌作用。（E）‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐ 4 ‐‐‐‐‐‐‐‐yré‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐ was ‐‐‐‐‐‐‐‐‐‐一was- ‐‐‐‐‐‐‐‐‐‐‐‐ 4？-‐‐‐‐‐‐‐‐‐‐‐‐‐‐5å？-‐‐‐‐‐‐‐‐‐‐‐‐ was？-‐‐‐‐‐‐‐‐‐‐‐‐waså？-‐‐‐ 5-（4-Chlorostyryl）‐1,3,4-Oxathiazol−2-1？的效果最佳，在所有测试浓度下的集落形成单位（CFU）/ mL仅在小于
• 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。
• Catalytic, Transition-Metal-Free Semireduction of Propiolamide Derivatives: Scope and Mechanistic Investigation
  作者：R. Justin Grams、Christopher J. Garcia、Connor Szwetkowski、Webster L. Santos

  DOI：10.1021/acs.orglett.0c02567

  日期：2020.9.4

  We report a transition-metal-free trans-selective semireduction of alkynes with pinacolborane and catalytic potassium tert-butoxide. A variety of 3-substituted primary and secondary propiolamides, including an analog of FK866, a potent nicotinamide mononucleotide adenyltransferase (NMNAT) inhibitor, are reduced to the corresponding (E)-3-substituted acrylamide derivatives in up to 99% yield with >99:1

  我们报道了频哪醇硼烷和催化叔丁醇钾对炔烃的无过渡金属反式选择性半还原。各种 3-取代的一级和二级丙炔酰胺，包括 FK866 的类似物（一种有效的烟酰胺单核苷酸腺苷酸转移酶 (NMNAT) 抑制剂），可被还原为相应的 ( E )-3-取代的丙烯酰胺衍生物，产率高达 99%，且 >99 ：1 E / Z选择性。机理研究表明，活化的路易斯酸碱配合物将氢化物转移到α-碳上，然后以反式方式快速质子化。
• 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。