[(1S)-(benzhydrylidene-amino)-3-cyano-propyl]-phosphonic acid diethyl ester | 874303-46-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(1S)-(benzhydrylidene-amino)-3-cyano-propyl]-phosphonic acid diethyl ester
• 英文别名: (4S)-4-(benzhydrylideneamino)-4-[diethoxy(oxido)phosphaniumyl]butanenitrile
• CAS: 874303-46-5
• 化学式: C₂₁H₂₅N₂O₃P
• 分子量: 384.415
• InChiKey: JXAHVSPXDWWLQU-FQEVSTJZSA-N

物化性质

• 沸点：
  509.8±50.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  77.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  diethyl (((diphenylmethylene)amino)methyl)phosphonate 、 丙烯腈 在 (R)-13-[2-(3,4-dimethoxyphenyl)ethyl]-8,9,12,13,14,15,17,18-octahydro-11H-dinaphtho[1,2-p:1,2-n][1,4,10,13,7]tetraoxazacycloheptadecine 作用下， 以 甲苯 为溶剂， 反应 0.17h， 生成 [(1S)-(benzhydrylidene-amino)-3-cyano-propyl]-phosphonic acid diethyl ester
  参考文献：
  名称：

  BINOL-based azacrown ether catalyzed enantioselective Michael addition: asymmetric synthesis of α-aminophosphonates

  摘要：

  Several novel 1.1'-bi-2-naphthyl-appended azacrown ethers with donor side-arms were synthesized and applied for the first time as chiral catalysts in the asymmetric Michael addition of an N-protected aminomethylenephosphonate onto acrylonitriles, resulting in high diastereoselectivity and enantioselectivity. The absolute configuration of the adduct was determined from its experimental and calculated CD spectra. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.02.002

文献信息

• Enantioselective synthesis of substituted α-aminophosphonates catalysed by <scp>d</scp>-glucose-based crown ethers: pursuit of the origin of stereoselectivity
  作者：Son Truong Pham、Zsolt Rapi、Péter Bakó、Imre Petneházy、András Stirling、Zsuzsa Jászay

  DOI：10.1039/c7nj03345a

  日期：——

  N-protected aminomethylenephosphonate onto acrylic acid derivatives and trans-β-nitrostyrene. Among these crown ethers, three are new. Michael adducts were formed with good to excellent enantio- and diastereoselectivities. Combined MM and QM calculations have revealed that suitable side arms on the crown ether beneficially affect the position of the central sodium cation, which in turn helps enhance the stereocontrol

  将几种与苯基-β- D-吡喃葡萄糖苷退火的单氮杂-15-冠-5型大环化合物用作手性催化剂，用于将N-保护的氨基亚甲基膦酸酯对映体选择性加成到丙烯酸衍生物和反式-β-硝基苯乙烯上。在这些冠醚中，有三个是新的。迈克尔加合物形成的对映选择性和非对映选择性都很好。MM和QM的组合计算表明，冠醚上合适的侧臂有利地影响了中央钠阳离子的位置，进而通过允许底物与催化剂之间的紧密接触，有助于增强立体控制。