N-benzyl-3-(4-chlorophenyl)-2-cyanoprop-2-enamide | 345368-05-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: N-benzyl-3-(4-chlorophenyl)-2-cyanoprop-2-enamide
• CAS: 345368-05-0
• 化学式: C₁₇H₁₃ClN₂O
• mdl: MFCD01441327
• 分子量: 296.756
• InChiKey: ATDVCJFBNWTISS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.058
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzyl-3-(4-chlorophenyl)-2-cyanoprop-2-enamide 在 S-α,α-双(3,5-二三氟甲基苯基)脯氨醇三甲基硅醚 、 三乙基硅烷 、 三氟化硼乙醚 、 对硝基苯甲酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 12.5h， 生成 1-benzyl-4-(4-chlorophenyl)-5-methyl-2-oxopiperidine-3-carbonitrile 、 (3R,4R,5R)-1-benzyl-4-(4-chlorophenyl)-5-methyl-2-oxopiperidine-3-carbonitrile
  参考文献：
  名称：

  One-Pot Synthesis of Optically Enriched 2-Piperidinones from Aliphatic Aldehydes and Cyanoacrylamides

  摘要：

  A highly stereoselective one-pot reaction of aliphatic aldehydes and cyanoacrylamides has been developed. The one-pot reaction includes an organocatalytic Michael addition followed by an intramolecular hemiaminalization. After reduction, optically enriched 2-piperidinones with three contiguous chiral centers were obtained in up to 95% yield and 9:1 dr with 99% ee.

  DOI：

  10.1021/ol401951g

文献信息

• One-Pot Synthesis of Optically Enriched 2-Piperidinones from Aliphatic Aldehydes and Cyanoacrylamides
  作者：Ying He、Tai-Ran Kang、Quan-Zhong Liu、Lian-Mei Chen、Yi-Lian Tu、Ya-Jun Liu、Tang-Bin Chen、Zhi-Qiang Wang、Jie Liu、Yong-Mei Xie、Jin-Liang Yang、Long He

  DOI：10.1021/ol401951g

  日期：2013.8.16

  A highly stereoselective one-pot reaction of aliphatic aldehydes and cyanoacrylamides has been developed. The one-pot reaction includes an organocatalytic Michael addition followed by an intramolecular hemiaminalization. After reduction, optically enriched 2-piperidinones with three contiguous chiral centers were obtained in up to 95% yield and 9:1 dr with 99% ee.