fumaric acid mono-p-bromoanilide | 843664-90-4

• 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: fumaric acid mono-p-bromoanilide
• 英文别名: 3-[(4-bromoanilino)carbonyl]prop-2-enoic acid；fumaric acid mono-N-(4-bromophenyl)amide；3-(N-(4-Bromophenyl)carbamoyl)prop-2-enoic acid；(E)-4-(4-bromoanilino)-4-oxobut-2-enoic acid
• CAS: 843664-90-4
• 化学式: C₁₀H₈BrNO₃
• mdl: MFCD00027402
• 分子量: 270.082
• InChiKey: DSNFUZCLEZJCRN-AATRIKPKSA-N

物化性质

• 沸点：
  482.0±45.0 °C(Predicted)
• 密度：
  1.688±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  fumaric acid mono-p-bromoanilide 在 Grubbs catalyst first generation cesium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 67.0h， 生成 (1S,3aR,3bR,8aR,9aS)-2-Benzyl-9a-((E)-4-bromo-but-1-enyl)-5-(4-bromo-phenyl)-3,4-dioxo-1,2,3,3a,3b,4,5,6,8a,9a-decahydro-9-oxa-2,5-diaza-cyclopenta[a]azulene-1-carboxylic acid benzylamide
  参考文献：
  名称：

  Simultaneous accumulation of both skeletal and appendage-based diversities on tandem Ugi/Diels–Alder products

  摘要：

  Diversity-oriented organic synthesis (DOS) is a key concept for construction of skeletally diverse small molecule libraries to discover drug-like small molecules. Here, we describe a DOS class to transform a complex 7-oxanorbornene skeleton, which is readily accessible by a tandem Ugi/Diels-Alder reaction, into two heterotricycle skeletons selectively by using tandem ROM/CM/RCM reaction. In the present study, the mode of cyclization is pre-encoded by building blocks used in the complexity-generating tandem Ugi/Diels-Alder reaction. Since variable alkenes can be used in the CM reaction, our approach can be extended to construct both skeleton- and appendage-diverse small molecule libraries. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.147
• 作为产物：
  描述：

  富马酸单乙酯 、 4-溴苯胺 在 草酰氯 、 N,N-二甲基甲酰胺 、 caesium carbonate 、 氢氧化钾 、 水 作用下， 以 苯 、 四氢呋喃 为溶剂， 反应 8.0h， 以76%的产率得到fumaric acid mono-p-bromoanilide
  参考文献：
  名称：

  7-氧降冰片烯的化学特异性烯丙基化和多米诺复分解用于骨骼和附属物的多样性

  摘要：

  我们报告了一种基于串联 Ugi/Diels-Alder 反应和多米诺复分解反应的具有附属物多样性的骨架多样化杂环的合成策略。提出了酰胺羰基官能团与钌金属中心的缔合效应，以解释复分解产率的差异。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  DOI：

  10.1002/ejoc.200800781

文献信息

• Coordination chemistry of the transition metal carboxylates synthesized from the ligands containing peptide linkage
  作者：S. Shahzadi、S. Ali、S. Jabeen、N. Kanwal、U. Rafique、A. N. Khan

  DOI：10.1134/s1070328408010077

  日期：2008.1

  Transition metal carboxylates, i.e., 3-[(2,4,6-trichloroanilino)carbonyl]prop-2-enoic acid and 3-[(4-bromoanilino)carbonyl]prop-2-enoic acid have been synthesized. The unimolar and bimolar substituted products have been characterized by elemental analysis, IR, UV-Vis spectroscopy, 1H NMR, and atomic absorption. IR data show the bidentate nature of the carboxylate group. The transition metal complexes were tested in vitro against a number of microorganisms to assess their biocidal properties.

  合成了过渡金属羧酸盐，即3-[(2,4,6-三氯苯胺)羰基]丙-2-烯酸和3-[(4-溴苯胺)羰基]丙-2-烯酸。这些单取代和双取代的产物通过元素分析、红外光谱、紫外-可见光谱、1H核磁共振和原子吸收进行表征。红外数据表明羧酸根具有二齿配位的特性。过渡金属配合物在体外与多种微生物进行测试，以评估其杀菌特性。
• Parallel synthesis of tandem Ugi/Diels–Alder reaction products on a soluble polymer support directed toward split-pool realization of a small molecule library
  作者：Masato Oikawa、Minoru Ikoma、Makoto Sasaki

  DOI：10.1016/j.tetlet.2004.11.115

  日期：2005.1

  A series of parallel reactions were carried out for the tandem Ugi/Diels–Alder reaction on our MPEG–O–CH2- platform. Ninety-six out of a 100 entries were successful to give complex heterotricycles. The stereoselectivity was found not to be influenced by the building blocks used for amine and carboxylic acid components. An unexpected side pathway was found but was suppressed by employing appropriate

  在我们的MPEG-O-CH 2-平台上，针对串联Ugi / Diels-Alder反应进行了一系列平行反应。在100个条目中，有96个成功生成了复杂的杂环。发现立体选择性不受用于胺和羧酸组分的结构单元的影响。发现了意外的旁通路，但是通过采用适当的反应条件可以抑制这种旁通路。该反应也在固相上进行，通过采用分流池法，可以潜在地实现更大的文库。
• Design, synthesis and biological evaluation of novel spiro-quinazolinone derivatives as chitin synthase inhibitors and antifungal agents
  作者：Chuanbiao Du、Xinlong Yang、Yan Long、Xueqing Lang、Lige Liu、Yajie Xu、Hu Wu、Yiwen Chu、Xiaolei Hu、Junfeng Deng、Qinggang Ji

  DOI：10.1016/j.ejmech.2023.115388

  日期：2023.7

  quinazolinone and the inherent feature of spirocycle to design novel chitin synthase inhibitors that possess mode of action different from that of the currently used antifungal agents. Among them, the spiro[thiophen-quinazolin]-one derivatives containing α, β-unsaturated carbonyl fragments had shown inhibitory activities against chitin synthase and antifungal activities. The enzymatic experiments showed that

  基于喹唑啉酮的生物活性和螺环的固有特性，构建了一系列螺环喹唑啉酮支架，设计出与目前使用的抗真菌药物作用方式不同的新型几丁质合酶抑制剂。其中，含有α，β-不饱和羰基片段的螺[噻吩-喹唑啉]-酮衍生物显示出对几丁质合酶的抑制活性和抗真菌活性。酶促实验表明，在16个化合物中，化合物12d、12g、12j、12l和12m对几丁质合酶具有抑制作用，IC50值分别为 116.7 ± 19.6 μM、106.7 ± 14.2 μM、102.3 ± 9.6 μM、122.7 ± 22.2 μM 和 136.8 ± 12.4 μM，与多氧菌素 B (IC 50  = 93.5 ± 11.1 μM)相当。酶促动力学参数测定表明化合物12g是几丁质合酶的非竞争性抑制剂。抗真菌试验表明，化合物12d、12g、12j、12l和12m对体外测试的四种菌株表现出广谱抗真菌活性。其中，化合物12g和12j化合物 12d、12l
• RASTOGI R. P.; GIRI S.; SINGH H.; RASTOGI S., PROC. SYMP. CHEM. REACT. NON-AQUEOUS MEDIA AND MOLTEN SALTS, HYDERABAD, 1+
  作者：RASTOGI R. P.、 GIRI S.、 SINGH H.、 RASTOGI S.

  DOI：——

  日期：——
• Chemospecific Allylation and Domino Metathesis of 7-Oxanorbornenes for Skeletal and Appendage Diversity
  作者：Minoru Ikoma、Masato Oikawa、Makoto Sasaki

  DOI：10.1002/ejoc.200800781

  日期：——

  We report a synthetic strategy for skeletally diverse heterocycles featuring appendage diversity based on a tandem Ugi/Diels–Alder reaction followed by domino metathesis. An associating effect of the amide carbonyl functionality to the ruthenium metal center is proposed in order to account for the difference in the metathesis yields. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  我们报告了一种基于串联 Ugi/Diels-Alder 反应和多米诺复分解反应的具有附属物多样性的骨架多样化杂环的合成策略。提出了酰胺羰基官能团与钌金属中心的缔合效应，以解释复分解产率的差异。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)