β-acetamido-β-(2-bromophenyl)-4-chloropropiophenone | 1186585-89-6

• 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: β-acetamido-β-(2-bromophenyl)-4-chloropropiophenone
• 英文别名: N-[1-(2-bromophenyl)-3-(4-chlorophenyl)-3-oxopropyl]acetamide
• CAS: 1186585-89-6
• 化学式: C₁₇H₁₅BrClNO₂
• 分子量: 380.669
• InChiKey: ZCHUATOYNDTCAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  对氯苯乙酮 、 邻溴苯甲醛 、 乙腈 在 copper(II) phthalocyanine 、 乙酰氯 作用下， 反应 3.5h， 以82%的产率得到β-acetamido-β-(2-bromophenyl)-4-chloropropiophenone
  参考文献：
  名称：

  以酞菁铜（II）为可重用催化剂的N-取代β-氨基酮衍生物的新型高立体选择性多组分合成

  摘要：

  具有取代基的N-取代的β-氨基酮衍生物的立体选择性合成在许多情况下已经通过使用铜（II）酞菁铜作为催化剂的一锅多组分方法来实现，在苯环上包括一个或两个极性杂原子。该新工艺适用于包含多种基材，用于构建高度功能化的曼尼希型结构支架。所使用的催化剂被循环再利用以重复反应。

  DOI：

  10.1016/j.tetlet.2011.04.016

文献信息

• Highly <i>Anti</i>-Selective One-Pot Multicomponent Synthesis of Mannich-Type N-Acylated <font>β</font>-Amino Acid Derivatives by Copper or Sodium Salt Catalysis
  作者：D. Bahulayan、V. S. Shinu、P. Pramitha、S. Arun、B. Sheeja

  DOI：10.1080/00397911.2010.537008

  日期：2012.4.15

  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.
• 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.