o-Bromo-N-acryloylanilide | 102804-43-3

• 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: o-Bromo-N-acryloylanilide
• 英文别名: N-(2-bromophenyl)acrylamide；EL-1015；N-(2-Bromophenyl)prop-2-enamide
• CAS: 102804-43-3
• 化学式: C₉H₈BrNO
• 分子量: 226.073
• InChiKey: SQBJWIXWJHGHDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 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：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  o-Bromo-N-acryloylanilide 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 sodium hydride 、 caesium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 3.34h， 生成 3-苄基-1,3-二氢-1-甲基-2H-吲哚-2-酮
  参考文献：
  名称：

  Rh-Catalyzed Domino Addition–Enolate Arylation: Generation of 3-Substituted Oxindoles via a Rh(lll) Intermediate

  摘要：

  A Rh-catalyzed domino conjugate addition-arylation sequence via a Rh(III) intermediate is reported. This process involving a proposed intramolecular oxidative addition of a rhodium enolate was utilized to achieve the synthesis of 3-substituted oxindole derivatives in moderate to excellent yields.

  DOI：

  10.1021/acs.orglett.5b01737
• 作为产物：
  描述：

  1-溴-2-硝基苯 在 铁粉 、 氯化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 20.0h， 生成 o-Bromo-N-acryloylanilide
  参考文献：
  名称：

  Discovery and Structure–Activity Relationship of Potent and Selective Covalent Inhibitors of Transglutaminase 2 for Huntington’s Disease

  摘要：

  Tissue transglutaminase 2 (TG2) is a multifunctional protein primarily known for its calcium-dependent enzymatic protein cross-linking activity via isopeptide bond formation between glutamine and lysine residues. TG2 overexpression and activity have been found to be associated with Huntington's disease (HD); specifically, TG2 is up-regulated in the brains of HD patients and in animal models of the disease. Interestingly, genetic deletion of TG2 in two different HD mouse models, R6/1 and R6/2, results in improved phenotypes including a reduction in neuronal death and prolonged survival. Starting with phenylacrylamide screening hit 7d, we describe the SAR of this series leading to potent and selective TG2 inhibitors. The suitability of the compounds as in vitro tools to elucidate the biology of TG2 was demonstrated through mode of inhibition studies, characterization of druglike properties, and inhibition profiles in a cell lysate assay.

  DOI：

  10.1021/jm201310y

文献信息

• Design, synthesis, antiviral and cytostatic evaluation of novel isoxazolidine nucleotide analogues with a carbamoyl linker
  作者：Kamil Kokosza、Jan Balzarini、Dorota G. Piotrowska

  DOI：10.1016/j.bmc.2013.01.007

  日期：2013.3

  phorylnitrone and N-arylacrylamides in good yields. cis- and trans-isoxazolidine phosphonates obtained herein were evaluated for activity against a broad range of DNA and RNA viruses. None of the compounds were endowed with antiviral activity at subtoxic concentrations. Isoxazolidines having phenyl substituted with halogen (Ar = 2-F-C6H4; 3-Br-C6H4; and 4-Br-C6H4) have been found to inhibit proliferation

  5-芳基氨基甲酰基-2-甲基异恶唑烷-3-基-3-膦酸酯已经由N-甲基-C-二乙氧基磷酰基硝酮和N-芳基丙烯酰胺以良好收率合成。评估了本文获得的顺式和反式异恶唑烷膦酸盐对广泛的 DNA 和 RNA 病毒的活性。没有一种化合物在亚毒性浓度下具有抗病毒活性。已发现具有被卤素取代的苯基的异恶唑烷（Ar = 2-FC 6 H 4；3-Br-C 6 H 4；和 4-Br-C 6 H 4）可抑制 L1210、CEM 和 HeLa 细胞的增殖带集成电路50在 100–170 μM 范围内。
• Aryl radical cyclisations involving an amide group in the linking chain
  作者：Keith Jones、John M. D. Storey

  DOI：10.1039/c39920001766

  日期：——

  Cyclisation of 7, 8 and 9via their derived aryl radicals gives products arising from addition of the aryl radical to the acryloyl double bond exclusively.

  7、8和9的环化通过其衍生的芳基自由基生成的产物，专门是芳基自由基与丙烯酰基双键的加成产物。
• An efficient synthesis of spiro[cyclohexane-1,3′-indol-2′(3′H)-ones]via radical cyclisation
  作者：Keith Jones、Mervyn Thompson、Colin Wright

  DOI：10.1039/c39860000115

  日期：——

  Treatment of the o-bromo-N-acryloylanilides (4) with tri-n-butylstannane leads to the formation of 3-substituted- and 3,3-disubstituted-2-oxindoles (5) in high yield.

  用三正丁基锡烷处理邻-溴-N-丙烯腈（4）导致高产率地形成3-取代的和3,3-二取代的-2-氧吲哚（5）。
• Solid-Phase Synthesis of Indol-2-ones by Microwave-Assisted Radical ­Cyclization
  作者：Koichi Fukase、Hisashi Akamatsu、Shoichi Kusumoto

  DOI：10.1055/s-2004-820052

  日期：——

  Solid-phase synthesis of indol-2-ones (2-oxindoles) by means of aryl radical cyclization of resin-bound N-(2-bromo­phenyl)acrylamides using Bu3SnH is described. Among various solvents tested, DMF was found to be the best choice for the radical cyclization inducing a reagent concentration effect of the polymer support. The reaction proceeded smoothly under microwave irradiation to give the desired indol-2-ones within a very short reaction time in comparison to conventional thermal heating. In this reaction, various indol-2-ones were synthesized by using commercially available 2-bromoanilines and acryloyl chloride derivatives.

  描述了一种通过使用Bu3SnH对树脂结合的N-(2-溴苯基)丙烯酰胺进行芳基自由基环化，从而实现Indol-2-酮（2-氧喹啉）的固相合成。在测试的各种溶剂中，DMF被认为是自由基环化的最佳选择，能够引发聚合物支撑的试剂浓度效应。在微波辐射下，反应顺利进行，与传统的热加热相比，在极短的反应时间内获得所需的Indol-2-酮。在此反应中，使用商业可得的2-溴苯胺和丙烯酰氯衍生物合成了多种Indol-2-酮。
• Intramolecular reactions using amide links: Aryl radical cyclisation of silylated acryloylanilides
  作者：Keith Jones、James Wilkinson、Richard Ewin

  DOI：10.1016/s0040-4039(00)78372-9

  日期：1994.10

  Aryl radical cyclisations of situ silylated o-bromoacryloylanilides are presented and shown to lead to N-unsubstituted oxindoles and dihydroquinolones in very different ratios than those previously observed for the N-alkyl o-bromoacryloylanilides.

  呈现了原位甲硅烷基化的邻-溴丙烯酰氰化物的芳基自由基环化，并显示出以与先前观察到的对N-烷基邻-溴丙烯酰氰化物的比率非常不同的比率导致N-未取代的羟吲哚和二氢喹诺酮。