N,2-diphenylpropanamide | 37002-50-9

• 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-diphenylpropanamide
• 英文别名: (2R)-N,2-diphenylpropanamide
• CAS: 37002-50-9
• 化学式: C₁₅H₁₅NO
• 分子量: 225.29
• InChiKey: PIZLNJQSSMQFOE-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  (R)-(-)-2-苯基丙酸 在 氯化亚砜 、 sodium carbonate 作用下， 以 苯 为溶剂， 反应 6.0h， 生成 N,2-diphenylpropanamide
  参考文献：
  名称：

  Potapov, V. M.; Dem'yanovich, V. M.; Solov'eva, L. D., Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, p. 2240 - 2245

  摘要：

  DOI：

文献信息

• Asymmetric Markovnikov Hydroaminocarbonylation of Alkenes Enabled by Palladium-Monodentate Phosphoramidite Catalysis
  作者：Ya-Hong Yao、Hui-Yi Yang、Ming Chen、Fei Wu、Xing-Xing Xu、Zheng-Hui Guan

  DOI：10.1021/jacs.0c11249

  日期：2021.1.13

  n of alkenes with anilines has been developed for the atom-economical synthesis of 2-substituted propanamides bearing an α-stereocenter. A novel phosphoramidite ligand L16 was discovered which exhibited very high reactivity and selectivity in the reaction. This asymmetric Markovnikov hydroaminocarbonylation employs readily available starting materials and tolerates a wide range of functional groups

  已经开发了钯催化的烯烃与苯胺的不对称马尔科夫尼科夫氢氨基羰基化反应，用于原子经济合成带有 α-立体中心的 2-取代丙酰胺。发现了一种新的亚磷酰胺配体 L16，它在反应中表现出非常高的反应性和选择性。这种不对称 Markovnikov 氢氨基羰基化使用容易获得的起始材料并耐受范围广泛的官能团，从而为在环境条件下区域选择性和对映选择性合成 2-取代丙酰胺提供了一种简便而直接的方法。机理研究表明，该反应通过钯氢化物途径进行。
• Reaction of azides and enolisable aldehydes under the catalysis of organic bases and Cinchona based quaternary ammonium salts
  作者：Dario Destro、Sandra Sanchez、Mauro Cortigiani、Mauro F. A. Adamo

  DOI：10.1039/c7ob00799j

  日期：——

  preparation of amides starting from azides and enolisable aldehydes. The reaction proceeded via the formation of triazoline intermediates that were converted into amides via Lewis acid catalysis. Preliminary studies on the preparation of triazolines under chiral phase transfer catalysis are also presented, demonstrating that enantioenriched amides could be prepared from achiral aldehydes in moderate to low

  在本文中，我们报告了从叠氮化物和可烯化醛开始制备酰胺的两步过程。反应通过形成三唑啉中间体进行，该中间体通过路易斯酸催化转化为酰胺。还介绍了在手性相转移催化下制备三唑啉的初步研究，表明可以从中等至低对映选择性的非手性醛制备对映体富集的酰胺。
• Enantioselective Synthesis of Chiral Amides by a Phosphoric Acid Catalyzed Asymmetric Wolff Rearrangement**
  作者：Jia‐Bin Pan、Zhi‐Chun Yang、Xuan‐Ge Zhang、Mao‐Lin Li、Qi‐Lin Zhou

  DOI：10.1002/anie.202308122

  日期：2023.9.25

  The highly enantioselective synthesis of chiral amides was achieved by an asymmetric Wolff rearrangement. A bifunctional phosphoric acid catalyst not only expedited the transformation but also controlled the enantioselectivity. The developed method enables the asymmetric addition between potent nucleophilic reagents and ketene species and provides a new approach to chiral amides.

  通过不对称沃尔夫重排实现了手性酰胺的高度对映选择性合成。双功能磷酸催化剂不仅能加速转化，还能控制对映选择性。所开发的方法能够实现强效亲核试剂和乙烯酮物种之间的不对称加成，并提供了一种制备手性酰胺的新方法。
• General and Scalable Amide Bond Formation with Epimerization-Prone Substrates Using T3P and Pyridine
  作者：Joshua R. Dunetz、Yanqiao Xiang、Aaron Baldwin、Justin Ringling

  DOI：10.1021/ol201875q

  日期：2011.10.7

  The mild combination of T3P (n-propanephosphonic acid anhydride) and pyridine has been developed for low-epimerization amide bond formation and implemented for the synthesis of a key intermediate to a glucokinase activator. This robust method is general for the coupling of various racemization-prone acid substrates and amines, including relatively non-nucleophilic anilines, and provides amides in high yields with very low epimerization. With easy reaction setup and product isolation, this protocol offers several practical and experimental benefits.
• Pettersson, Arkiv foer Kemi, 1956, vol. 10, p. 297,299, 302
  作者：Pettersson

  DOI：——

  日期：——