tetraethyl-4-aminophenylmethylene-1,1-bisphosphonate | 188752-81-0

• 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-4-aminophenylmethylene-1,1-bisphosphonate
• 英文别名: 4-aminophenylmethane-bisphosphonic tetraethyl ester；tetraethyl (4-aminophenyl)methylenephosphonate；4-[Bis(diethoxyphosphoryl)methyl]aniline
• CAS: 188752-81-0
• 化学式: C₁₅H₂₇NO₆P₂
• 分子量: 379.33
• InChiKey: LFKVROYJGKXUBJ-UHFFFAOYSA-N

物化性质

• 沸点：
  516.0±50.0 °C(Predicted)
• 密度：
  1.205±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  97.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tetraethyl-4-aminophenylmethylene-1,1-bisphosphonate 在 盐酸 、 sodium nitrite 、 水 作用下， 以 水 为溶剂， 反应 2.0h， 以50%的产率得到tetraethyl ((4-hydroxyphenyl)methylene)bis(phosphonate)
  参考文献：
  名称：

  Preparation Of Tetraethyl-4-Hydroxyphenylmethylene-1,1-Bisphosphonate By Hydroxy-De-Diazoniation of The Corresponding Diazonium Salt Of Tetraethyl-4-Aminophenylmethylene-1,1-Bisphosphonate

  摘要：

  Bisphosphonates are widely used in diagnosis and therapy of different bone diseases. They are useful agents in osteotic vectorization of antitumor and antiinflammatory drugs because of their potential to accumulate in the inorganic bone matrix hydroxylapatite. Hence, there is great interest in alkyl-bisphosphonates. containing functional groups advantageous For further synthetic modification, as structural units for coupling with the drug. We report on the synthesis of tetraethyl-4-hydroxyphenylmethylene-1,1-bisphosphonate 8 by hydroxy-de-diazoniation of the diazonium salt 7, prepared by diazotation of the corresponding amine tetraethyl-3-aminophenyl methylene-1,1-bisphosphonate 6.

  DOI：

  10.1080/10426500008076326
• 作为产物：
  描述：

  tetraethyl-4-(trifluoroacetylamino)phenylmethylene-1,1-bisphosphonate 在 氢氧化钾 、 水 、 氯化铵 作用下， 以 水 为溶剂， 反应 5.0h， 以92%的产率得到tetraethyl-4-aminophenylmethylene-1,1-bisphosphonate
  参考文献：
  名称：

  Phosphonated Fluoroquinolones, Antibacterial Analogs Thereof, and Methods for the Prevention and Treatment of Bone and Joint Infections

  摘要：

  本发明涉及磷酸化氟喹诺酮及其抗菌类似物，以及使用这些化合物的方法。这些化合物可用作抗生素，用于预防和/或治疗骨骼和关节感染，特别是用于预防和/或治疗骨髓炎。

  公开号：

  US20080287396A1

文献信息

• QUINOLONE ANTIBACTERIAL AGENTS LINKED TO OSTEOTROPIC BISPHOSPHONATE MOIETIES
  作者：T. Pieper、B. K. Keppler

  DOI：10.1080/10426500108040581

  日期：2001.3.1

  Bisphosphonates are widely used in diagnosis and therapy of different bone diseases. Due to their potential to accumulate in the inorganic bone matrix hydroxylapatite they are useful agents in osteotic vectorization of different types of drugs. We linked bisphosphonate moieties to antibacterial quinolones like norfloxacin to enable a selective targeting of these agents to bone tissue. The quinolones (1,4-dihydro-4-oxo-quinoline-3-carboxylic acids) were modified at position 1 and 7 using alkylbisphosphonates with ethene-, amino- and carboxylic-groups. After coupling with the quinolones, the alkylbisphosphonic esters could smoothly be hydrolyzed via the corresponding silyl esters to obtain the free bisphosphonic acids.
• Phosphonated Fluoroquinolones, Antibacterial Analogs Thereof, and Methods for the Prevention and Treatment of Bone and Joint Infections
  申请人：Delorme Daniel

  公开号：US20080287396A1

  公开（公告）日：2008-11-20

  The present invention relates to phosphonated fluoroquinolones, antibacterial analogs thereof, and methods of using such compounds. These compounds are useful as antibiotics for prevention and/or the treatment of bone and joint infections, especially for the prevention and/or treatment of osteomyelitis.

  本发明涉及磷酸化氟喹诺酮及其抗菌类似物，以及使用这些化合物的方法。这些化合物可用作抗生素，用于预防和/或治疗骨骼和关节感染，特别是用于预防和/或治疗骨髓炎。
• Preparation Of Tetraethyl-4-Hydroxyphenylmethylene-1,1-Bisphosphonate By Hydroxy-De-Diazoniation of The Corresponding Diazonium Salt Of Tetraethyl-4-Aminophenylmethylene-1,1-Bisphosphonate
  作者：T. Pieper、B. K. Keppler

  DOI：10.1080/10426500008076326

  日期：2000.2

  Bisphosphonates are widely used in diagnosis and therapy of different bone diseases. They are useful agents in osteotic vectorization of antitumor and antiinflammatory drugs because of their potential to accumulate in the inorganic bone matrix hydroxylapatite. Hence, there is great interest in alkyl-bisphosphonates. containing functional groups advantageous For further synthetic modification, as structural units for coupling with the drug. We report on the synthesis of tetraethyl-4-hydroxyphenylmethylene-1,1-bisphosphonate 8 by hydroxy-de-diazoniation of the diazonium salt 7, prepared by diazotation of the corresponding amine tetraethyl-3-aminophenyl methylene-1,1-bisphosphonate 6.