{[benzyl-(1-cyclohexylcarbamoyl-2-hydroxy-2-phenyl-vinyl)-carbamoyl]-methyl}-phosphonic acid diethyl ester | 652965-00-9

• 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: {[benzyl-(1-cyclohexylcarbamoyl-2-hydroxy-2-phenyl-vinyl)-carbamoyl]-methyl}-phosphonic acid diethyl ester
• 英文别名: (E)-2-[benzyl-(2-diethoxyphosphorylacetyl)amino]-N-cyclohexyl-3-hydroxy-3-phenylprop-2-enamide
• CAS: 652965-00-9
• 化学式: C₂₈H₃₇N₂O₆P
• 分子量: 528.585
• InChiKey: JHIODRYPMQISBM-CYYJNZCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.66
• 重原子数：
  37.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  105.17
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  {[benzyl-(1-cyclohexylcarbamoyl-2-hydroxy-2-phenyl-vinyl)-carbamoyl]-methyl}-phosphonic acid diethyl ester 在 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 12.5h， 以274 mg的产率得到1-benzyl-5-oxo-3-phenyl-2,5-dihydro-1H-pyrrole-2-carboxylic acid cyclohexyl amide
  参考文献：
  名称：

  Highly Substituted Pyrrolidinones and Pyridones by 4-CR/2-CR Sequence

  摘要：

  By combining a Ugi four-component reaction of isocyanides, phosphonoacetic acids, primary amines, and glyoxals or alternatively 3-keto aldehydes with a subsequent Wittig ring-closing reaction (using the Horner/Wadsworth/Emmons variant (HWE)), highly substituted 5-oxo-2,5dihydro-1H-pyrrole-2-carboxylic acid amides and 6-oxo-1,2,3,6-tetrahydro-pyridine-2-carboxylic acid amides can be assembled, respectively. The corresponding tandem of a Passerini reaction on 3-keto aldehydes and subsequent Wittig ring closure does not afford the expected six-membered 6-oxo-3,6-dihydro-2H-pyran-2-carboxylic acid amides but instead leads to the formation of 4-oxo-pent-2-enoic acid amides via an elimination route.

  DOI：

  10.1021/ol035787n
• 作为产物：
  描述：

  二乙基磷乙酸 、 异氰环已烷 、 苯基丙醇水合物 、 苄胺 以 甲醇 为溶剂， 以76%的产率得到{[benzyl-(1-cyclohexylcarbamoyl-2-hydroxy-2-phenyl-vinyl)-carbamoyl]-methyl}-phosphonic acid diethyl ester
  参考文献：
  名称：

  Highly Substituted Pyrrolidinones and Pyridones by 4-CR/2-CR Sequence

  摘要：

  By combining a Ugi four-component reaction of isocyanides, phosphonoacetic acids, primary amines, and glyoxals or alternatively 3-keto aldehydes with a subsequent Wittig ring-closing reaction (using the Horner/Wadsworth/Emmons variant (HWE)), highly substituted 5-oxo-2,5dihydro-1H-pyrrole-2-carboxylic acid amides and 6-oxo-1,2,3,6-tetrahydro-pyridine-2-carboxylic acid amides can be assembled, respectively. The corresponding tandem of a Passerini reaction on 3-keto aldehydes and subsequent Wittig ring closure does not afford the expected six-membered 6-oxo-3,6-dihydro-2H-pyran-2-carboxylic acid amides but instead leads to the formation of 4-oxo-pent-2-enoic acid amides via an elimination route.

  DOI：

  10.1021/ol035787n

文献信息

• Highly Substituted Pyrrolidinones and Pyridones by 4-CR/2-CR Sequence
  作者：Barbara Beck、Anne Picard、Eberhardt Herdtweck、Alexander Dömling

  DOI：10.1021/ol035787n

  日期：2004.1.1

  By combining a Ugi four-component reaction of isocyanides, phosphonoacetic acids, primary amines, and glyoxals or alternatively 3-keto aldehydes with a subsequent Wittig ring-closing reaction (using the Horner/Wadsworth/Emmons variant (HWE)), highly substituted 5-oxo-2,5dihydro-1H-pyrrole-2-carboxylic acid amides and 6-oxo-1,2,3,6-tetrahydro-pyridine-2-carboxylic acid amides can be assembled, respectively. The corresponding tandem of a Passerini reaction on 3-keto aldehydes and subsequent Wittig ring closure does not afford the expected six-membered 6-oxo-3,6-dihydro-2H-pyran-2-carboxylic acid amides but instead leads to the formation of 4-oxo-pent-2-enoic acid amides via an elimination route.