tetraethyl ((2-chlorophenylamino)methylene)bisphosphonate | 59611-62-0

• 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: tetraethyl ((2-chlorophenylamino)methylene)bisphosphonate
• 英文别名: N-[bis(diethoxyphosphoryl)methyl]-2-chloroaniline
• CAS: 59611-62-0
• 化学式: C₁₅H₂₆ClNO₆P₂
• 分子量: 413.775
• InChiKey: JLAAHCHNKFTCKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tetraethyl ((2-chlorophenylamino)methylene)bisphosphonate 在 盐酸 作用下， 生成 [(2-Chloro-phenylamino)-phosphono-methyl]-phosphonic acid
  参考文献：
  名称：

  Gross,H. et al., Journal fur praktische Chemie (Leipzig 1954), 1976, vol. 318, p. 116 - 126

  摘要：

  DOI：
• 作为产物：
  描述：

  [(2-Chloro-phenylimino)-(diethoxy-phosphoryl)-methyl]-phosphonic acid diethyl ester 在 sodium tetrahydroborate 作用下， 生成 tetraethyl ((2-chlorophenylamino)methylene)bisphosphonate
  参考文献：
  名称：

  Gross,H. et al., Journal fur praktische Chemie (Leipzig 1954), 1976, vol. 318, p. 116 - 126

  摘要：

  DOI：

文献信息

• A facile synthesis of aminomethylene bisphosphonates catalyzed by ytterbium perfluorooctanoate under ionic liquid condition
  作者：Mudumala Veera Narayana Reddy、Jongsik Kim、Yeon Tae Jeong

  DOI：10.1016/j.jfluchem.2011.10.005

  日期：2012.3

  Three-component reactions of amines, triethylorthoformate and diethyl phosphite are efficiently catalyzed by ytterbium perfiuorooctanoate [Yb(PFO)(3)] in 1-butyl-3-methylimidazolium chloride ([bmim][Cl]) ionic liquid, giving the corresponding aminomethylene bisphosphonates in good yields. The catalyst can be recovered and reused for several times without any significant loss of activity. (C) 2011 Elsevier B.V. All rights reserved.
• ——
  作者：V. I. Krutikov、A. V. Erkin、P. A. Pautov、M. M. Zolotukhina

  DOI：10.1023/a:1024775501781

  日期：——

  A series of substituted aminomethylenebisphosphonates is prepared by reaction of dialkyl hydrogen phosphites with triethyl orthoformate and corresponding heteryl- or arylamine. The determining factor in the formation of the target products is appearance of an intermediate associate between the ortho ester and amine. The rate and selectivity of the process can be increased by using a nonpolar solvent to stabilize the transition state of the reaction. Crown ether catalysis increases the selectivity of the process by 10-20%. The synthesized aminomethylenebisphosphonates whose structure was established by NMR spectroscopy exhibit a moderate antibacterial and anticholinesterase activity.