(E)-N-(chloromethyl)-3-phenyl-N-[(1S)-1-phenylethyl]prop-2-enamide | 138261-14-0

• 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: (E)-N-(chloromethyl)-3-phenyl-N-[(1S)-1-phenylethyl]prop-2-enamide
• CAS: 138261-14-0
• 化学式: C₁₈H₁₈ClNO
• 分子量: 299.8
• InChiKey: BVMRBJCIEXBQHC-LHNRBYRGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.49
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (E)-N-(chloromethyl)-3-phenyl-N-[(1S)-1-phenylethyl]prop-2-enamide 在 氨 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 (E)-N-(aminomethyl)-3-phenyl-N-[(1S)-1-phenylethyl]prop-2-enamide
  参考文献：
  名称：

  A new route to the synthesis of amino acids through the mercury cyclization of chiral amidals

  摘要：

  By means of the mercury cyclization of the unsaturated amidals 3a-e, obtained from the reaction of 1,3,5-tris-[(S)-phenylethyl]hexahydrotriazine (1) and alpha,beta-unsaturated acyl chlorides, diastereomeric mixtures of imidazolidin-4-ones 5-8 and perihydropyrimidin-4-ones 9-10 have been synthesized and easily separated by flash chromatography. The subsequent hydrolysis under acid conditions of the separated heterocycles affords respectively D or L alpha- and beta-amino acids. The regiochemistry of the cyclization has been studied, depending on the substituents of the double bond. Furthermore the absolute configuration of the newly introduced stereogenic center has been attributed on the basis of the H-1 NMR spectra of the heterocycles.

  DOI：

  10.1021/jo00030a010
• 作为产物：
  描述：

  1,3,5-tris((S)-α-methylbenzyl)hexahydrotriazine 、 3-苯基-2-丙烯酰氯 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 (E)-N-(chloromethyl)-3-phenyl-N-[(1S)-1-phenylethyl]prop-2-enamide
  参考文献：
  名称：

  A new route to the synthesis of amino acids through the mercury cyclization of chiral amidals

  摘要：

  By means of the mercury cyclization of the unsaturated amidals 3a-e, obtained from the reaction of 1,3,5-tris-[(S)-phenylethyl]hexahydrotriazine (1) and alpha,beta-unsaturated acyl chlorides, diastereomeric mixtures of imidazolidin-4-ones 5-8 and perihydropyrimidin-4-ones 9-10 have been synthesized and easily separated by flash chromatography. The subsequent hydrolysis under acid conditions of the separated heterocycles affords respectively D or L alpha- and beta-amino acids. The regiochemistry of the cyclization has been studied, depending on the substituents of the double bond. Furthermore the absolute configuration of the newly introduced stereogenic center has been attributed on the basis of the H-1 NMR spectra of the heterocycles.

  DOI：

  10.1021/jo00030a010