N-Benzoyl-3-benzyloxyanilin | 55872-35-0

• 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: N-Benzoyl-3-benzyloxyanilin
• 英文别名: phenyl-N-[3-(phenylmethoxy)phenyl]carboxamide；N-benzoyl-3-benzyloxyaniline；N-(3-phenylmethoxyphenyl)benzamide
• CAS: 55872-35-0
• 化学式: C₂₀H₁₇NO₂
• 分子量: 303.36
• InChiKey: HFFCCLDOINYYHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-Benzoyl-3-benzyloxyanilin 在 氢氧化钾 、 氯胺 、 sodium hydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 6.75h， 生成 1-(3-benzyloxyphenylamino)pyrrole
  参考文献：
  名称：

  Synthesis and antibacterial activity of 1-(arylamino)-1H-pyrroles and 4-(1H-pyrrol-1-ylimino)-2,5-cyclohexadienes

  摘要：

  The syntheses of 1-(arylamino)-1H-pyrroles and 4-(1H-pyrrol-1-ylimino)-2-5-cyclohexadienes are described. Several of these compounds express in vitro antibacterial activity or can be metabolized to show in vitro antibacterial activity, and a few examples have shown efficacy against tuberculosis in mice. One compound, N,N'-(2,5-cyclohexadiene-1,4-diylidene)bis-1H-pyrrol-1-amine, is completely effective at 6.25 mg/kg against Mycobacterium tuberculosis H37Rv.

  DOI：

  10.1021/jm00143a011
• 作为产物：
  描述：

  苯甲酸乙酯 、 1-硝基-3-苯基甲氧基苯 在 chromium chloride 、 三甲基氯硅烷 、 magnesium 、 4,4'-二叔丁基-2,2'-二吡啶 、 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以77%的产率得到N-Benzoyl-3-benzyloxyanilin
  参考文献：
  名称：

  铬催化的镁与羰基的C–O键活化，使硝基芳烃酰胺化

  摘要：

  在这里，我们报道了铬与镁催化的羰基C–O键活化，从而使酯与硝基芳烃酰胺化。通过使用镁作为还原剂和氯代三甲基硅烷作为添加剂，低成本的氯化铬（III）在促进酰胺化方面显示出高反应活性。它为使用廉价且空气稳定的硝基芳烃作为氨基源合成重要的酰胺基序提供了分步经济策略。

  DOI：

  10.1021/acs.orglett.9b00554

文献信息

• N-Phenylbenzamide derivatives as alternative oxidase inhibitors: Synthesis, molecular properties, 1H-STD NMR, and QSAR
  作者：Paulo C.S. Costa、Mario R.O. Barsottini、Maria L.L. Vieira、Bárbara A. Pires、Joel S. Evangelista、Ana C.M. Zeri、Andrey F.Z. Nascimento、Jaqueline S. Silva、Marcelo F. Carazzolle、Gonçalo A.G. Pereira、Maurício L. Sforça、Paulo C.M.L. Miranda、Silvana A. Rocco

  DOI：10.1016/j.molstruc.2020.127903

  日期：2020.5

  DRX and 1H-NMR-STD. Single crystal X-ray diffraction showed intra- and intermolecular interactions of 3FH in solid-state and elucidated its 3D structural configuration. 1H-NMR-STD allowed us to derive protein-ligand interactions in a membrane-mimetic system and evidenced an outstanding interaction of 3FH with this enzyme. Results of both biological assays were used as input to Quantitative Structure-Activity

  摘要 在目前的工作中，制备了 117 种 N-苯基苯甲酰胺 (NPD)，并针对来自真菌病原体 Moniliophthora perniciosa 的重组 AOX 进行了评估。1H、13C NMR、FTIR 和质谱提供了 NPD 的结构信息。使用模型酵母毕赤酵母在两种不同的测定中测试文库化合物作为替代氧化酶抑制剂：细胞生长和耗氧量测定。活性最强的化合物 3FH 通过 DRX 和 1H-NMR-STD 进一步表征。单晶 X 射线衍射显示固态 3FH 的分子内和分子间相互作用，并阐明了其 3D 结构构型。1H-NMR-STD 使我们能够在膜模拟系统中推导出蛋白质-配体相互作用，并证明了 3FH 与这种酶的显着相互作用。
• Heteroaryl alkyl piperazine derivatives
  申请人：——

  公开号：US20030216409A1

  公开（公告）日：2003-11-20

  Novel compounds of the general formula: 1 and pharmaceutically acceptable acid addition salts thereof, wherein the compounds are useful in therapy to protect skeletal muscles against damage resulting from trauma or to protect skeletal muscles subsequent to muscle or systemic diseases such as intermittent claudication, to treat shock conditions, to preserve donor tissue and organs used in transplants, in the treatment of diabetes, in the treatment of cardiovascular diseases including atrial and ventricular arrhythmias, Prinzmetal's (variant) angina, stable angina, and exercise induced angina, congestive heart disease, and myocardial infarction.

  通用公式：1的新化合物及其药学上可接受的酸盐，其中这些化合物在治疗中用于保护骨骼肌免受外伤引起的损伤或在骨骼肌或系统性疾病（如间歇性跛行）后保护骨骼肌，用于治疗休克状态，保护供体组织和器官用于移植，治疗糖尿病，治疗心血管疾病，包括心房和心室心律失常，普林兹梅塔（变异）心绞痛，稳定型心绞痛和运动诱发性心绞痛，充血性心脏病和心肌梗死。
• 1-(Arylamino)-and 1-(arylimino)-pyrroles
  申请人：Sterling Drug Inc.

  公开号：US04051147A1

  公开（公告）日：1977-09-27

  1-(Arylamino)pyrroles and 1-(arylimino)pyrroles, useful as antibacterial agents, are prepared by reaction of an arylhydrazine or arylhydrazone with a 2,5-di-lower-alkoxytetrahydrofuran or with an alkanedione; by reaction of a 1-arylaminopyrrole with an oxalyl dihalide followed by oxidative hydrolysis of the product; by condensation of a 1-aminopyrrole with a quinone; or by oxidation or reduction of a respective 1-(arylamino)pyrrole or 1-(arylimino)pyrrole.

  1-(芳基氨基)吡咯和1-(芳基亚胺基)吡咯，作为抗菌剂，可通过芳基肼或芳基肼酮与2,5-二低烷氧基四氢呋喃或烷二酮反应制备；通过1-芳基氨基吡咯与草酰二卤代物反应，然后氧化水解产物；通过1-氨基吡咯与醌的缩合反应；或者通过氧化或还原相应的1-(芳基氨基)吡咯或1-(芳基亚胺基)吡咯制备。
• Heteroaryl alkyl piperazine derivatives as fatty acid oxidation inhibitors
  申请人：——

  公开号：US20040029889A1

  公开（公告）日：2004-02-12

  Novel compounds of the general formula (I): and pharmaceutically acceptable acid addition salts thereof, wherein the compounds are useful in therapy to protect skeletal muscles against damage resulting from trauma or to protect skeletal muscles subsequent to muscle or systemic diseases such as intermittent claudication, to treat shock conditions, to preserve donor tissue and organs used in transplants, in the treatment of cardiovascular diseases including atrial and ventricular arrhythmias, Prinzmetal's (variant) angina, stable angina, and exercise induced angina, congestive heart disease, and myocardial infarction. 1

  一般式（I）的新化合物及其药物可接受的酸盐，其中这些化合物在治疗中对保护骨骼肌免受创伤引起的损伤或在肌肉或全身疾病（如间歇性跛行）后保护骨骼肌，治疗休克病状，保存用于移植的供体组织和器官，在治疗心血管疾病包括心房和心室心律失常，普林兹梅塔尔（变异）心绞痛，稳定型心绞痛和运动性心绞痛，充血性心力衰竭和心肌梗死方面有用。
• Deoxygenative Radical Boration of Inert Amides via a Combination of Relay and Cooperative Catalysis
  作者：Feng Jiang、Jing'an Li、Xiaoming Wang

  DOI：10.1002/chem.202301199

  日期：2023.6.22

  One of the most challenging tasks in organic synthesis is to develop novel methodologies for rapid construction of complex molecules starting from easily available yet inert raw materials. In this context, multi‐catalysis strategies have attracted great attention in the discovery of new reactivity profiles that may allow access to many difficult or unattainable transformations. So far the deoxygenative functionalization of ubiquitous amides is usually achieved by nucleophilic attack on the imine or iminium ion intermediate formed via activation of the C=O bond, and these functionalization reagents were often confined to C‐based nucleophiles, which largely limited the diversity of the resultant amines. Herein, we disclose a combined strategy of relay and cooperative catalysis with a triple iridium‐photoredox‐organocatalysis system to achieve an unprecedented reductive boration of amides, affording valuable α‐amino boron products which are viable building blocks. In this transformation, the Ir‐catalyzed semi‐reduction of amides is successfully incorporated with photo‐organic catalyzed nucleophilic boryl radical addition, thus delivering the corresponding α‐boryl amines in high efficiency.

  摘要 有机合成领域最具挑战性的任务之一是开发新型方法，以便从易于获得的惰性原料出发，快速构建复杂分子。在这种情况下，多催化策略在发现新的反应性概况方面引起了极大的关注，这些反应性概况可能允许进行许多困难或无法实现的转化。迄今为止，无处不在的酰胺的脱氧官能化通常是通过亲核攻击 C=O 键活化形成的亚胺或亚铵离子中间体来实现的，而这些官能化试剂通常仅限于 C 型亲核物，这在很大程度上限制了所生成胺的多样性。在此，我们揭示了一种接力催化和协同催化的组合策略，利用三重铱-光氧化-有机催化系统实现了前所未有的酰胺还原丁化，得到了有价值的α-氨基硼产物，这些产物是可行的构筑基块。在这一转化过程中，铱催化的酰胺半还原与光催化的亲核硼酸基加成成功地结合在一起，从而高效地得到了相应的α-硼酸胺。