dimethyl (1-amino-1,5-dimethyl-hex-4-enyl)phosphonate | 156517-99-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: dimethyl (1-amino-1,5-dimethyl-hex-4-enyl)phosphonate
• 英文别名: 2-Dimethoxyphosphoryl-6-methylhept-5-en-2-amine
• CAS: 156517-99-6
• 化学式: C₁₀H₂₂NO₃P
• 分子量: 235.263
• InChiKey: WVHONNQFQHIJNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dimethyl (1-amino-1,5-dimethyl-hex-4-enyl)phosphonate 在 sodium hydroxide 、 sodium tetrahydroborate 、 mercury(II) diacetate 、 间氯过氧苯甲酸 作用下， 以 正戊烷 为溶剂， 反应 13.0h， 生成
  参考文献：
  名称：

  Stereoselective Synthesis, Molecular Geometry, and Oxidation of (5-Isopropyl-2-methylpyrrolidin-2-yl)phosphonates

  摘要：

  Intramolecular aminomercuration of (1-amino-1,5-dimethylhex-4-enyl)phosphonates was shown to be regio- and stereoselective and to lead to (5-isopropyl-2-methylpyrrolidin-2-yl)phosphonates. The stereoselectivity was shown to be controlled by the experimental conditions. The configurations of the chiral carbons for the diastereomers were determined by X-ray and NMR analysis. Oxidation of the pyrrolidin-2-ylphosphonates with m-CPBA led to diastereomeric nitroxides exhibiting different phosphorus splitting and different half-lives.

  DOI：

  10.1021/jo00091a024
• 作为产物：
  描述：

  6-甲基-5-庚烯-2-酮 、 亚磷酸二甲酯 在 氨 作用下， 反应 4.0h， 以70%的产率得到dimethyl (1-amino-1,5-dimethyl-hex-4-enyl)phosphonate
  参考文献：
  名称：

  Stereoselective Synthesis, Molecular Geometry, and Oxidation of (5-Isopropyl-2-methylpyrrolidin-2-yl)phosphonates

  摘要：

  Intramolecular aminomercuration of (1-amino-1,5-dimethylhex-4-enyl)phosphonates was shown to be regio- and stereoselective and to lead to (5-isopropyl-2-methylpyrrolidin-2-yl)phosphonates. The stereoselectivity was shown to be controlled by the experimental conditions. The configurations of the chiral carbons for the diastereomers were determined by X-ray and NMR analysis. Oxidation of the pyrrolidin-2-ylphosphonates with m-CPBA led to diastereomeric nitroxides exhibiting different phosphorus splitting and different half-lives.

  DOI：

  10.1021/jo00091a024

文献信息

• Stereoselective Synthesis, Molecular Geometry, and Oxidation of (5-Isopropyl-2-methylpyrrolidin-2-yl)phosphonates
  作者：Francois Le Moigne、Paul Tordo

  DOI：10.1021/jo00091a024

  日期：1994.6

  Intramolecular aminomercuration of (1-amino-1,5-dimethylhex-4-enyl)phosphonates was shown to be regio- and stereoselective and to lead to (5-isopropyl-2-methylpyrrolidin-2-yl)phosphonates. The stereoselectivity was shown to be controlled by the experimental conditions. The configurations of the chiral carbons for the diastereomers were determined by X-ray and NMR analysis. Oxidation of the pyrrolidin-2-ylphosphonates with m-CPBA led to diastereomeric nitroxides exhibiting different phosphorus splitting and different half-lives.