N-[1-(2-nitrophenyl)-3-(4-nitrophenyl)-3-oxopropyl]pentanamide | 1186586-00-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: N-[1-(2-nitrophenyl)-3-(4-nitrophenyl)-3-oxopropyl]pentanamide
• CAS: 1186586-00-4
• 化学式: C₂₀H₂₁N₃O₆
• 分子量: 399.403
• InChiKey: KGYLKBFHTQGYCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  戊腈 、 对硝基苯乙酮 、 邻硝基苯甲醛 在 copper(ll) sulfate pentahydrate 、 丙酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以60%的产率得到N-[1-(2-nitrophenyl)-3-(4-nitrophenyl)-3-oxopropyl]pentanamide
  参考文献：
  名称：

  Highly Anti-Selective One-Pot Multicomponent Synthesis of Mannich-Type N-Acylated β-Amino Acid Derivatives by Copper or Sodium Salt Catalysis

  摘要：

  A stereo-defined process has been developed for the synthesis of Mannich-type products using readily available copper sulfate or sodium chloride as catalyst. Good to excellent diastereoselectivity has been achieved for a broad array of substrates. The observed diastereoselectivity is explained on the basis of the steric interaction between the acyloxy group of the aldehyde carbon and the more hindered alpha-substituted enolate anion. This steric interaction helps the addition to take place through the less-hindered face to produce the anti-isomers predominantly.Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2010.537008

文献信息

• An efficient green MCR protocol for the stereoselective synthesis of β-acetamido ketones catalyzed by Selectfluor™
  作者：V.S. Shinu、B. Sheeja、E. Purushothaman、D. Bahulayan

  DOI：10.1016/j.tetlet.2009.06.022

  日期：2009.8

  An efficient, green, room temperature process for the stereoselective synthesis of beta-amido ketones employing a one-pot multi-component reaction of aromatic aldehydes, alpha-substituted or alpha-unsubstituted ketones, an acid chloride, and a nitrile in presence of catalytic amount of Selectfluor (TM) is described. The process offers advantages such as high anti-selectivity, shorter reaction time, energy efficiency, and simple work-up. (c) 2009 Elsevier Ltd. All rights reserved.