N-(2-methoxyphenyl)butyramide | 255873-38-2

• 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-(2-methoxyphenyl)butyramide
• 英文别名: N-(2-methoxyphenyl)butanamide
• CAS: 255873-38-2
• 化学式: C₁₁H₁₅NO₂
• mdl: MFCD00791300
• 分子量: 193.246
• InChiKey: QVIZZPNBLFFJKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 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-(2-methoxyphenyl)butyramide 在 tetraphosphorus decasulfide 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 32.0h， 生成 3-Biphenyl-4-yl-4-(2-methoxy-phenyl)-5-propyl-4H-[1,2,4]triazole
  参考文献：
  名称：

  4,5-二苯基-1,2,4-三唑衍生物的发现作为人类V（1A）受体的新型一类选择性拮抗剂。

  摘要：

  在寻找针对人类V（1A）受体的新型新型选择性拮抗剂时，Yamanouchi化学文库的高通量筛选（HTS）使用表达克隆的人类V（1A）（hV（1A））受体的CHO细胞进行发现具有新颖的4,5-二苯基-1,2,4-的5-（4-联苯基）-4-（2-甲氧基苯基）-3-甲基-1,2,4-三唑（3）三唑结构。随后的与3相关的一系列4,5-二苯基-1,2,4-三唑衍生物的结构-活性关系研究表明，4,5-二苯基-1,2,4-三唑结构在对hV（1A）受体具有高亲和力，并且将碱性胺部分引入4-苯基环的甲氧基部分可有效提高对hV（1A）受体的亲和力和相对于hV（2）的选择性）受体。

  DOI：

  10.1016/s0968-0896(02)00009-3
• 作为产物：
  描述：

  2-硝基苯甲醚 、 丁酰氯 在 溶剂黄146 、 三乙胺 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 以64%的产率得到N-(2-methoxyphenyl)butyramide
  参考文献：
  名称：

  Reductive amidation of nitroarenes: a practical approach for the amidation of natural products

  摘要：

  A simple and practical approach for the one-pot conversion of nitroarenes into amide derivatives has been developed. Zinc and acetic acid are utilized as a reducing agent, and acyl chloride and triethylamine are used as the acylating agent in DMF with good yield (similar to 60%) of the amide. This method was applicable to manzamine A (1), where the yield of 6-cyclohexamidemanzamine A (7) was significantly improved (56%) by this approach relative to (17%) by beginning with the amine. (c) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2009.04.061

文献信息

• Ion Channel Modulators
  申请人：Zelle Robert

  公开号：US20070281937A1

  公开（公告）日：2007-12-06

  The invention relates to compounds, compositions comprising the compounds, and methods of using the compounds and compound compositions. The compounds, compositions, and methods described herein can be used for the therapeutic modulation of ion channel function, and treatment of disease and disease symptoms, particularly those mediated by certain calcium channel subtype targets.

  这项发明涉及化合物、包含这些化合物的组合物，以及使用这些化合物和化合物组合物的方法。本文描述的化合物、组合物和方法可用于治疗调节离子通道功能，以及治疗疾病和疾病症状，特别是那些由特定钙通道亚型靶点介导的疾病。
• Inhibitors of VEGF receptor and HGF receptor signaling
  申请人：Saavedra Mario Oscar

  公开号：US20070004675A1

  公开（公告）日：2007-01-04

  The invention relates to the inhibition of VEGF receptor signaling and HGF receptor signaling. The invention provides compounds and methods for inhibiting VEGF receptor signaling and HGF receptor signaling. The invention also provides compositions and methods for treating cell proliferative diseases and conditions

  该发明涉及抑制VEGF受体信号和HGF受体信号。该发明提供了抑制VEGF受体信号和HGF受体信号的化合物和方法。该发明还提供了治疗细胞增殖性疾病和病况的组合物和方法。
• Efficient amide formation from arylamines and esters promoted by AlCl3/Et3N: an experimental and computational investigation
  作者：Xinli Tong、Zhangshun Ren、Xiaolong Qü、Qiwu Yang、Wenqin Zhang

  DOI：10.1007/s11164-012-0517-x

  日期：2012.10

  Efficient and selective preparation of amides from arylamines and esters has been achieved with an AlCl3/Et3N pair under mild conditions. A large number of arylamines were successfully acylated to the corresponding amides in high yields and short reaction times. For instance, a 94% yield of p-bromoacetanilide was obtained from p-bromoaniline and ethyl acetate in 10 min at room temperature. In addition, a computational study on the N-acylation of amines was performed using density functional theory. It was found that the energy barrier for N-acylation of aniline is 10 kcal/mol higher than that of methylamine. In the presence of AlCl3, the activation energy for the N-acylation of aniline was reduced by 27.7 kcal/mol with the endothermic process becoming exothermic. In this work, the efficient and selective preparation of amides from arylamines and esters has been performed successfully with an AlCl3/Et3N pair under mild conditions. A large number of arylamines were acylated to the corresponding amides with high yields and short reaction times. In addition, a computational study on the N-acylation of amines has been carried out using the density functional theory (DFT) method.

  在温和条件下，利用AlCl3/Et3N配对实现了芳香胺与酯的高效选择性酰胺制备。大量芳香胺成功地被酰化为相应的酰胺，产率高且反应时间短。例如，从对溴苯胺和乙酸乙酯在室温下反应10分钟获得了94%的对溴乙酰苯胺。此外，使用密度泛函理论对胺的N-酰化进行了计算研究。研究发现，苯胺的N-酰化能量障碍比甲胺高10 kcal/mol。在 的存在下，苯胺的N-酰化活化能降低了27.7 kcal/mol，导致吸热过程转变为放热过程。本文成功实现了在温和条件下利用 /Et3N配对从芳香胺与酯中高效选择性地制备酰胺，大量芳香胺被酰化为相应的酰胺，产率高且反应时间短。此外，还利用密度泛函理论（DFT）方法对胺的N-酰化进行了计算研究。
• Organocatalytic Asymmetric Annulation between Hydroxymaleimides and Nitrosoarenes: Stereoselective Preparation of Chiral Quaternary <i>N</i>-Hydroxyindolines
  作者：Yu Yang、Hong-Xia Ren、Feng Chen、Zheng-Bing Zhang、Ying Zou、Chao Chen、Xiang-Jia Song、Fang Tian、Lin Peng、Li-Xin Wang

  DOI：10.1021/acs.orglett.7b00893

  日期：2017.6.2

  highly effective asymmetric annulation of nitrosoarenes with hydroxymaleimides catalyzed by a chiral bifunctional amine squaramide catalyst has been disclosed. A wide range of highly fused chiral N-hydroxyindolines with two consecutive quaternary stereocenters and multifunctional groups were directly and effectively prepared in excellent yields (up to >99%) with complete regioselective cyclization and

  已公开了一种由手性双官能胺方酸方胺催化剂催化的亚硝基芳烃与羟基马来酰亚胺的不寻常且高度有效的不对称环化反应。直接和有效地制备了具有两个连续的季位立体中心和多功能基团的各种高度融合的手性N-羟基二氢吲哚，具有良好的收率（高达99％），具有完全的区域选择性环化和出色的立体选择性（高达> 99：1 dr 99％ee）。通过精细地转化为一系列新的手性二氢吲哚，可以很好地证明新反应和目标手性实体的效率和潜力。
• Atropselective synthesis of <i>N</i>-aryl pyridones <i>via</i> dynamic kinetic resolution enabled by non-covalent interactions
  作者：Jamie S. Sweet、Ruichen Wang、Panagiotis Manesiotis、Paul Dingwall、Peter C. Knipe

  DOI：10.1039/d2ob00177b

  日期：——

  Hydrogen bonding in ortho-phenols enables enantioselective synthesis of axially chiral 2-pyridones via dynamic kinetic resolution.

  在邻酚中的氢键使得通过动态动力学分辨实现轴手性2-吡啶酮的对映选择性合成。