N-[1-(2-oxo-2-phenylethyl)-3-phenylallyl]acetamide | 916597-91-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[1-(2-oxo-2-phenylethyl)-3-phenylallyl]acetamide
• 英文别名: N-(1-oxo-1,5-diphenylpent-4-en-3-yl)acetamide；N-(5-oxo-1,5-diphenylpent-1-en-3-yl)acetamide
• CAS: 916597-91-6
• 化学式: C₁₉H₁₉NO₂
• 分子量: 293.365
• InChiKey: ZCCHNBCTQGNZTA-UHFFFAOYSA-N

物化性质

• 熔点：
  120-121 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  546.0±50.0 °C(Predicted)
• 密度：
  1.118±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  46.17
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  肉桂醛 、 苯乙酮 、 乙腈 在 copper(ll) sulfate pentahydrate 、 乙酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以65%的产率得到N-[1-(2-oxo-2-phenylethyl)-3-phenylallyl]acetamide
  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

• Triphenylphosphine-Catalyzed, Novel, One-Pot, Multicomponent Synthesis of Functionalized<font>β</font>-Acetamido Carbonyls
  作者：Shyam Babu Singh、Pankaj Kumar Verma、Kamleshwar Tiwari、Mandavi Singh、Preyas Ankit、Shahin Fatma、Jagdamba Singh、Kamla Prasad Tiwari

  DOI：10.1080/00397911.2013.873939

  日期：2014.6.18

  An efficient triphenylphosphine-catalyzed synthesis of beta-acetamido carbonyls via multicomponent reaction of aromatic aldehydes, enolizable ketones or beta-keto esters, acid chlorides and acetonitrile at room temperature is described. The process is remarkably simple, environmentally benign, and uses Lewis base for the first time in such type of reaction.