N-(4-甲基苄基)丙酰胺 | 65608-93-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(4-甲基苄基)丙酰胺
• 英文名称: N-(4-methylbenzyl)propionamide
• 英文别名: N-(4-methylbenzyl)propanamide；N-[(4-methylphenyl)methyl]propanamide
• CAS: 65608-93-7
• 化学式: C₁₁H₁₅NO
• mdl: MFCD03365204
• 分子量: 177.246
• InChiKey: NXEHUVBLMTVJGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  丙腈 、 4-甲基苄胺 在 Iron(III) nitrate nonahydrate 作用下， 反应 24.0h， 以82%的产率得到N-(4-甲基苄基)丙酰胺
  参考文献：
  名称：

  An iron-catalysed synthesis of amides from nitriles and amines

  摘要：

  The cheap, commercially available iron complex, Fe(NO3)(3)center dot 9H(2)O, has been used to catalyse the formation of amides by the addition of amines to nitriles. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.05.021

文献信息

• Kinetics and mechanism of the aminolysis of thiophenyl methylacetates in acetonitrile
  作者：Hyuck Keun Oh、Jin Hee Yang、In Ho Cho、Hai Whang Lee、Ikchoon Lee

  DOI：10.1002/1097-4601(2000)32:8<485::aid-kin6>3.0.co;2-x

  日期：——

  and cross-interaction constant ρXZ is relatively large and positive (0.90). These trends are consistent with the rate-limiting breakdown of a tetrahedral intermediate, T ± . The proposed mechanism is also supported by adherence of the rate data to the reactivity-selectivity principle (RSP). The kinetic isotope effects, kH/kD, are greater than unity (1.3-1.4) suggesting a possibility of hydrogen-bonded

  交叉相互作用常数 ρXZ 较大且为正（0.90）。这些趋势与四面体中间体 T ± 的限速分解一致。速率数据遵守反应选择性原则 (RSP) 也支持所提出的机制。动力学同位素效应 kH/kD 大于单位 (1.3-1.4)，表明可能存在氢键四中心过渡态。激活参数 ΔH ≠ 和 ΔS ≠ 与这种过渡态结构一致。
• Highly Selective Amidation of Benzylic Alcohols with Nitriles. A Modified Ritter Reaction
  作者：H. Firouzabadi、A. R. Sardarian、H. Badparva

  DOI：10.1080/00397919408012637

  日期：1994.3

  Abstract Benzyl alcohols react selectively with different nitriles in the presence of a catalytic amount of boron trifluoride and produce amides in high yields. Deactivated p-nitrobenzyl, allylic, primary, secondary, and tertiary saturated alcohols do not react.

  摘要 苄醇在催化量的三氟化硼存在下选择性地与不同的腈反应并以高产率产生酰胺。失活的对硝基苄基、烯丙基、伯、仲和叔饱和醇不反应。
• CONTROLLED CYCLIZATION OF PEPTOIDS TO FORM CHIRAL DIKETOPIPERAZINES
  申请人：Triad National Security, LLC

  公开号：US20200131140A1

  公开（公告）日：2020-04-30

  The present disclosure provides improved methods for controlled cyclization of peptoid dimers to form N,N′-2,5-diketopiperazines (N,N′-2,5-DKPs) with significant selectivity. In at least some examples, selectivity is based on a serendipitous conglomeration of slow exchange of amide rotamers, steric repulsion from the degree of α-substitution, and the geometric bulk of an amine nucleophile. By varying reaction conditions, the selectivity of the reaction and formation of a particular N,N′-2,5-DKP can be switched. The cyclization works in the presence of a variety of protection groups and diverse functionalities. The teachings herein provide techniques for synthesizing N,N′-2,5-DKPs that can be readily docked with drug candidates for shuttling across the blood brain barrier. This method provides a facile way to produce substituted DKPs containing groups ready for post-modification to include docking drug candidates.

  本公开提供了改进的方法，用于控制肽烷二聚体的环化，形成具有显著选择性的N，N'-2,5-二酮哌嗪（N，N'-2,5-DKP）。在至少一些示例中，选择性基于酰胺旋转体的缓慢交换的偶然混合，α-取代程度的立体排斥以及胺亲核试剂的几何体积。通过改变反应条件，可以切换反应的选择性和特定N，N'-2,5-DKP的形成。该环化反应在各种保护基和多样化的官能团存在下进行。本文提供了用于合成可轻松与药物候选物交会以穿越血脑屏障的N，N'-2,5-DKP的技术。该方法提供了一种简便的方法来产生含有用于后修饰的基团的取代DKP，以包括交会药物候选物。
• Ligands of Integrin Receptors
  申请人：Geneste Herve

  公开号：US20080221082A1

  公开（公告）日：2008-09-11

  The invention relates to the use of cyclic compounds as ligands of integrin receptors, in particular as ligands of the α V β 3 integrin receptor, the novel compounds themselves, their use, and pharmaceutical preparations comprising these compounds.

  本发明涉及将环状化合物用作整合素受体的配体，特别是用作αVβ3整合素受体的配体，以及这些新化合物本身、它们的用途和包含这些化合物的制药制剂。
• QUINUCLIDINE DERIVATIVES BINDING TO MUCARINIC M3 RECEPTORS
  申请人：Collingwood Stephen Paul

  公开号：US20100041887A1

  公开（公告）日：2010-02-18

  Compounds of formula I in salt or zwitterionic form wherein, wherein R 1 , R 2 , R 3 , and R 4 have the meanings as indicated in the specification, are useful for treating conditions that are mediated by the muscarinic M3 receptor. Pharmaceutical compositions that contain the compounds and a process for preparing the compounds are also described.

  具有式I的化合物，其以盐或双离子形式存在，其中R1、R2、R3和R4的含义如规范中所示，可用于治疗由肌肉乙酰胆碱M3受体介导的疾病。还描述了含有这些化合物的制药组合物和制备这些化合物的过程。