N-benzyl-2-phenoxyacetamide | 18861-15-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-benzyl-2-phenoxyacetamide
• 英文别名: N-benzyl-2-phenoxy-acetamide；N1-benzyl-2-phenoxyacetamide；N-benzyl(phenoxy)acetamide；phenoxy-acetic acid benzylamide；Phenoxy-essigsaeure-benzylamid；C-Phenoxy-N-benzyl-acetamid
• CAS: 18861-15-9
• 化学式: C₁₅H₁₅NO₂
• mdl: MFCD00446158
• 分子量: 241.29
• InChiKey: WPNWGIALOINNCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 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-benzyl-2-phenoxyacetamide 在 dimethyl sulfide borane 作用下， 以 乙二醇二甲醚 为溶剂， 反应 16.0h， 以50%的产率得到N-benzyl-N-(2-phenoxyethyl)amine
  参考文献：
  名称：

  Structure–Activity relationships among novel phenoxybenzamine-Related β-Chloroethylamines

  摘要：

  A series of beta-chloroethylamines 5-18, structurally related to the irreversible alpha(1)-adrenoceptor antagonist phenoxy-benzamine [PB, N-benzyl-N-(2-chloroethyl)-N-(1-methyl-2-phenoxyethyl)amine hydrochloride, 1] and the competitive antagonist WB4101 [N-(2,3-dihydro-1,4-benzodioxin-2-ylmethyl)-N-[2-(2,6-dimethoxyphenoxy)ethyl]amine hydrochloride, 2], were synthesized and evaluated for their activity at alpha-adrenoceptors of the epididymal and the prostatic portion of young CD rat vas deferens. All compounds displayed irreversible antagonist activity. Most of them showed similar antagonism at both alpha(1)- and alpha(2)-adrenoceptors, whereas compounds 13 and 18, lacking substituents on both the phenoxy group and the oxyamino carbon chain, displayed a moderate alpha(1)-adrenoceptor selectivity (10-35 times), which was comparable to that of PB. Compounds 14 and 15, belonging to the benzyl series and bearing, respectively, a 2-ethoxyphenoxy and a 2-i-propoxyphenoxy moiety, were the most potent alpha(1)-adrenoceptor antagonists with an affinity value similar to that Of PB (pIC(50) values of 7.17 and 7.06 versus 7.27). Interestingly, several compounds were able to distinguish two alpha(1)-adrenoceptor subtypes in the epididymal tissue, as revealed by the discontinuity of their inhibition curves. A mean ratio of 24:76 for these alpha(1)-adrenoceptors was determined from compounds 8-10, 12, and 15-17. Furthermore, compounds 9, 10, 12, 16a, and 16b showed higher affinity towards the minor population of receptors, whereas compounds 8, 15, and 17 preferentially inhibited the major population of alpha(1)-adrenoceptors. In addition, selected pharmacological experiments demonstrated the complementary antagonism of the two series of compounds and their different, preferential affinity for one of the two alpha(1)-adrenoceptor subtypes. In conclusion, we found beta-chloroethylamines that demonstrate a multiplicity of alpha(1)-adrenoceptors in the epididymal portion of young CD rat vas deferens and, as a consequence, they are possible useful tools for alpha(1)-adrenoceptor characterization. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00395-9
• 作为产物：
  描述：

  苯氧乙酸 在 Wang resin-CH₂-O-(...)-[4-(2,6-dichloro-1,3,5-triazine)] 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-benzyl-2-phenoxyacetamide
  参考文献：
  名称：

  一种用于合成酰氯的新型固相氯化剂

  摘要：

  将氰尿酰氯装载到改性的Wang树脂上，该树脂成功地用于将羧酸转化为其相应的酰氯。通过与各种胺或醇缩合形成相应的酰胺或酯，可以确认酰氯的形成。

  DOI：

  10.1016/s0040-4039(02)02190-1

文献信息

• Electrochemical generation and reactions of acyloxytriphenylphosphonium ions
  作者：Hidenobu Ohmori、Hatsuo Maeda、Masayuki Kikuoka、Toshihide Maki、Masaichiro Masui

  DOI：10.1016/s0040-4020(01)87066-6

  日期：1991.1

  undivided cell, of Ph3P in the presence of a carboxylic acid in CH2Cl2 containing 2,6-lutidinium perchlorate as the supporting electrolyte was shown to generate the corresponding acyloxyphosphonium ion, Ph3P+-OCOR, which was converted in situ to esters, amides, and β-lactams under mild conditions.

  结果表明，在羧酸存在下的CH 2 Cl 2中，含高氯酸2,6-lut啶鎓作为辅助电解质的PH 3 P在不分隔的电池中恒流电解会生成相应的酰氧基phosph离子Ph 3 P + -OCOR，在温和条件下原位转化为酯，酰胺和β-内酰胺。
• Ammonia-borane as a Catalyst for the Direct Amidation of Carboxylic Acids
  作者：P. Veeraraghavan Ramachandran、Henry J. Hamann

  DOI：10.1021/acs.orglett.1c00591

  日期：2021.4.16

  Ammonia-borane serves as an efficient substoichiometric (10%) precatalyst for the direct amidation of both aromatic and aliphatic carboxylic acids. In situ generation of amine-boranes precedes the amidation and, unlike the amidation with stoichiometric amine-boranes, this process is facile with 1 equiv of the acid. This methodology has high functional group tolerance and chromatography-free purification

  氨硼烷可作为芳族和脂族羧酸直接酰胺化的有效亚化学计量（10％）预催化剂。胺-硼烷的原位生成是在酰胺化之前进行的，与化学计量的胺-硼烷的酰胺化不同，此过程易于加入1当量的酸。该方法具有较高的官能团耐受性和无色谱法纯化，但不适合酯化。已经开发了后者的特征以制备含羟基和硫醇的酰胺。
• Solvent-Free Iron(III) Chloride-Catalyzed Direct Amidation of Esters
  作者：Blessing D. Mkhonazi、Malibongwe Shandu、Ronewa Tshinavhe、Sandile B. Simelane、Paseka T. Moshapo

  DOI：10.3390/molecules25051040

  日期：——

  work, we report the synthesis of these functional groups via an iron(iii) chloride-catalyzed direct amidation of esters. The reactions are conducted under solvent-free conditions and found to be compatible with a range of amine and ester substrates generating the desired amides in short reaction times and good to excellent yields at a catalyst loading of 15 mol%.

  酰胺官能团在具有多种有益应用的广泛有机化合物中很突出。在这项工作中，我们报告了通过氯化铁 (iii) 催化的酯直接酰胺化合成这些官能团。该反应在无溶剂条件下进行，发现与一系列胺和酯底物相容，可在较短的反应时间内生成所需的酰胺，并且在 15 mol% 的催化剂负载量下产率良好至极好。
• Direct amidation of non‐activated carboxylic acid and amine derivatives catalyzed by TiCp ₂ Cl ₂
  作者：Hui Wang、Wei Dong、Zhipeng Hou、Lidan Cheng、Xiufen Li、Longjiang Huang

  DOI：10.1002/aoc.5568

  日期：2020.5

  carboxylic acid and amine derivatives catalyzed by TiCp2Cl2. Arylacetic acid derivatives reacted with different amines to afford the corresponding amides in good to excellent yield except of aniline. Aryl formic acids failed to react with aniline but smoothly reacted with aliphatic amines and benzylamine in moderate to good yield, fatty acids reacting with benzyl and aliphatic amines give amides in good

  本文描述了由TiCp 2 Cl 2催化的非活化羧酸和胺衍生物的温和有效直接酰胺化反应。丁二酸衍生物与不同的胺反应以除苯胺以外的良好至优异的产率提供相应的酰胺。芳基甲酸不能与苯胺反应，但是可以与脂肪胺和苄胺平滑反应，收率中等至良好；脂肪酸与苄基和脂肪胺反应可以得到酰胺，收率很好。手性氨基酸衍生物无需外消旋就可以中等产率转化为酰胺。TiCp 2 Cl 2催化直接酰胺化的可能机理进行了讨论。该催化方法非常适用于低位阻芳基丙烯酸，除苯胺以外的具有不同低位阻胺的脂肪酸的酰胺化，以及芳基甲酸与苄基和脂族胺的酰胺化。
• Direct Amide Coupling of Non-activated Carboxylic Acids and Amines Catalysed by Zirconium(IV) Chloride
  作者：Helena Lundberg、Fredrik Tinnis、Hans Adolfsson

  DOI：10.1002/chem.201104055

  日期：2012.3.26

  Amidst the green: A green, mild and effective protocol for the direct formation of secondary and tertiary amides from non‐activated carboxylic acids and amines in good to excellent yields by employing ZrCl4 as the catalyst is presented (see scheme). The amide coupling protocol proved to be suitable for scaled up syntheses, and the mild reaction conditions conserve the enantiopurity of chiral starting

  在绿色之中：提出了一种绿色，温和而有效的方案，该方案可通过使用ZrCl 4作为催化剂，从非活化的羧酸和胺直接生成仲酰胺和叔酰胺，并获得良好或优异的收率（参见方案）。酰胺偶联方案被证明适合用于大规模合成，并且温和的反应条件保留了手性起始原料的对映体纯度。