diethyl (1-amino-1,5-dimethyl-hex-4-enyl)phosphonate | 156518-00-2

• 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: diethyl (1-amino-1,5-dimethyl-hex-4-enyl)phosphonate
• 英文别名: 2-Diethoxyphosphoryl-6-methylhept-5-en-2-amine
• CAS: 156518-00-2
• 化学式: C₁₂H₂₆NO₃P
• 分子量: 263.317
• InChiKey: PIBUGTFSBXSZDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  diethyl (1-amino-1,5-dimethyl-hex-4-enyl)phosphonate 生成
  参考文献：
  名称：

  Roubaud Valerie, Le Moigne Francois, Mercier Anne, Tordo Paul, Phosph., Sulfur and Silicon and Relat. Elem, 86 (1994) N 1-4, S 39-54

  摘要：

  DOI：
• 作为产物：
  描述：

  6-甲基-5-庚烯-2-酮 、 亚磷酸二乙酯 在 氨 作用下， 反应 4.0h， 以70%的产率得到diethyl (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

• An Improved Reduction Procedure in the Synthesis of Substituted Pyrrolidines via An Aminomercuration/Reduction Sequence of Primary Alkenylamines
  作者：Valérie Roubaud、François Le Moigne、Anne Mercier、Paul Tordo

  DOI：10.1080/00397919608003517

  日期：1996.4

  Aminomercuration/reduction sequence of delta-alkenylamines is a typical route to substituted pyrrolidines. Backward reaction to the starting material is a major drawback which occurs during sodium borohydride reduction of the intermediate organomercurial. We describe here a new reduction procedure which prevents almost completely this backward reaction and leads to significant increases in the yields of pyrrolidines.
• Roubaud Valerie, Le Moigne Francois, Mercier Anne, Tordo Paul, Phosph., Sulfur and Silicon and Relat. Elem, 86 (1994) N 1-4, S 39-54
  作者：Roubaud Valerie, Le Moigne Francois, Mercier Anne, Tordo Paul

  DOI：——

  日期：——
• 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.