N-(furan-2-ylmethyl)-3-phenylpropanamide | 6004-95-1

• 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-(furan-2-ylmethyl)-3-phenylpropanamide
• 英文别名: N-(2-furanylmethyl)-3-phenylpropanamide
• CAS: 6004-95-1
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: LDJRBCNFCKLPFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-呋喃甲胺 、 3-苯丙醇 在 3-甲基-2-丁酮 、 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 caesium carbonate 、 1,4-双(二苯基膦)丁烷 作用下， 以 叔丁醇 为溶剂， 反应 24.0h， 以54%的产率得到N-(furan-2-ylmethyl)-3-phenylpropanamide
  参考文献：
  名称：

  Ruthenium-catalysed oxidation of alcohols to amides using a hydrogen acceptor

  摘要：

  A wider investigation into the synthesis of secondary amides from primary alcohols using a hydrogen acceptor using commercially available [Ru(p-cymene)Cl-2](2) with bis(diphenylphosphino)butane (dppb) as the catalyst. The report looks at over 50 examples with varying functionality and steric bulk, whilst also covering the first reported results using microwave heating to effect the transformation. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.04.017

文献信息

• Facile direct synthesis of amides from trichloroethyl esters using catalytic DBU
  作者：Minh Thanh La、Hee-Kwon Kim

  DOI：10.1139/cjc-2018-0234

  日期：2018.12

  A practical method for the direct synthesis of amide compounds is described. Using small quantities of DBU as a catalyst, the direct conversion of 2,2,2-trichloroethyl esters to their corresponding...

  描述了直接合成酰胺化合物的实用方法。使用少量 DBU 作为催化剂，将 2,2,2-三氯乙酯直接转化为相应的...
• A Practical and General Amidation Method from Isocyanates Enabled by Flow Technology
  作者：Jason D. Williams、William J. Kerr、Stuart G. Leach、David M. Lindsay

  DOI：10.1002/anie.201807393

  日期：2018.9.10

  The addition of carbon nucleophiles to isocyanates represents a conceptually flexible and efficient approach to the preparation of amides. This general synthetic strategy has, however, been relatively underutilized owing to narrow substrate tolerance and the requirement for less favourable reaction conditions. Herein, we disclose a high‐yielding, mass‐efficient, and scalable method with appreciable

  将碳亲核试剂加至异氰酸酯代表了制备酰胺的概念上灵活且有效的方法。然而，由于窄的底物耐受性和对较不利的反应条件的要求，这种通用的合成策略尚未得到充分利用。本文中，我们公开了一种高产率，质量高效且可扩展的方法，该方法通过格氏试剂与异氰酸酯的反应形成酰胺，具有相当的官能团耐受性。通过流动化学的应用和亚化学计量量的CuBr 2的使用，已开发出该方法以涵盖广泛的底物，包括发现与先前公布的程序不兼容的反应物。
• A Hydroperoxide‐Mediated Decarboxylation of α‐Ketoacids Enables the Chemoselective Acylation of Amines
  作者：Takeshi Nanjo、Natsuki Kato、Xuan Zhang、Yoshiji Takemoto

  DOI：10.1002/chem.201904717

  日期：2019.12.5

  decarboxylative amidation of α-ketoacids by using inexpensive tert-butyl hydroperoxide (TBHP), which is characterized by high yields, a broad substrate scope, mild reaction conditions, and a unique chemoselectivity. These features enable the synthesis of peptides from amino acid derived α-ketoacids under preservation of the stereochemical information.

  迄今为止，酰胺键形成的策略，即有机合成中最基本和最重要的转变之一，主要集中在脱水反应上。在本文中，我们报告并证明了通过使用廉价的叔丁基氢过氧化物（TBHP）来生产α-酮酸的新型脱羧酰胺化技术的实用性，该技术的特点是收率高，底物范围宽，反应条件温和以及独特的化学选择性。这些特征使得能够在保留立体化学信息的情况下从氨基酸衍生的α-酮酸合成肽。
• Rhodium-catalyzed oxidative amidation of allylic alcohols and aldehydes: effective conversion of amines and anilines into amides
  作者：Zhao Wu、Kami L. Hull

  DOI：10.1039/c5sc03103f

  日期：——

  The rhodium-catalyzed oxidative amidation of allylic alcohols and aldehydes is reported. In situ generated [(BINAP)Rh]BF4 catalyzes the one-pot isomerization/oxidative amidation of allylic alcohols or direct amidation of aldehydes using acetone...

  报道了铑催化的烯丙基醇和醛的氧化酰胺化。原位生成的[（BINAP）Rh] BF 4催化烯丙基醇的一锅异构化/氧化酰胺化反应，或使用丙酮直接催化醛的酰胺化反应。
• Continuous-flow dehydrative amidation between carboxylic acids and amines using modified mixed metal oxides as solid acid catalysts
  作者：Haruro Ishitani、Kota Takeno、Masahiro Sasaya、Shū Kobayashi

  DOI：10.1039/d3cy00937h

  日期：——

  Dehydrative amidation reactions under continuous-flow conditions with solid acid catalysts were investigated. High performance molybdenum oxide-supported Zr–Sn mixed metal oxides were applied in reactions between aliphatic carboxylic acids and aliphatic amines, and the desired amides and cyclic imides were obtained in high yields with sufficient space–time yields.

  研究了在连续流动条件下使用固体酸催化剂的脱水酰胺化反应。将高性能氧化钼负载Zr-Sn混合金属氧化物应用于脂肪族羧酸和脂肪族胺之间的反应，以高产率和足够的时空收率获得了所需的酰胺和环状酰亚胺。