cis-1,2-bis-diethoxyphosphinylformamidocyclohexane | 1035449-31-0

• 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: cis-1,2-bis-diethoxyphosphinylformamidocyclohexane
• 英文别名: tetraethyl((((1R,2S)-cyclohexane-1,2-diyl)bis(azanediyl))bis(carbonyl))bis(phosphonate)；1-diethoxyphosphoryl-N-[(1S,2R)-2-(diethoxyphosphorylcarbonylamino)cyclohexyl]formamide
• CAS: 1035449-31-0
• 化学式: C₁₆H₃₂N₂O₈P₂
• 分子量: 442.386
• InChiKey: CTGDWFVRFOMDLZ-OKILXGFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  乙醇 、 在 lithium perchlorate 、 四丁基碘化铵 作用下， 反应 2.0h， 以84%的产率得到cis-1,2-bis-diethoxyphosphinylformamidocyclohexane
  参考文献：
  名称：

  电化学驱动的P–H氧化和官能化：由磷酰胺和醇类合成氨基甲酰基膦酸酯†

  摘要：

  据报道，使用n -Bu 4 NI作为催化剂，通过PH氧化和官能化反应，可从磷酰胺和醇中获得氨基甲酰基膦酸酯的电化学方法。在温和的反应条件下，以良好或优异的收率获得了一系列氨基甲酰基膦酸酯。电化学反应在恒定电流电解下进行，其中醇用作溶剂和底物，并且是有吸引力的绿色合成方法。

  DOI：

  10.1039/c8nj05739g

文献信息

• Carbamoylphosphonate Matrix Metalloproteinase Inhibitors 6: <i>cis</i>-2-Aminocyclohexylcarbamoylphosphonic Acid, A Novel Orally Active Antimetastatic Matrix Metalloproteinase-2 Selective Inhibitor—Synthesis and Pharmacodynamic and Pharmacokinetic Analysis
  作者：Amnon Hoffman、Bashir Qadri、Julia Frant、Yiffat Katz、Sudhakar R. Bhusare、Eli Breuer、Rivka Hadar、Reuven Reich

  DOI：10.1021/jm701087n

  日期：2008.3.13

  cis-2-Aminocyclohexylcarbamoylphosphonic acid (cis-ACCP) was evaluated in vitro and in two in vivo cancer metastasis models. It reduced metastasis formation in mice by similar to 90% when administered by a repetitive once daily dosing regimen of 50 mg/kg via oral or intraperitoneal routes and was nontoxic up to 500 mg/kg, following intraperitoneal administration daily for two weeks. Pharmacokinetic investigation of cis-ACCP in rats revealed distribution restricted into the extracellular fluid, which is the site of action for the antimetastatic activity and rapid elimination (t(1/2) similar to 19 min) from blood. Sustained and prolonged absorption (t(1/2) similar to 126 min) occurred via paracellular mechanism along the small and large intestine with overall bioavailability of 0.3%. The in vivo concentrations of cis-ACCP in the blood in rats was above the minimal concentration for antimetastatic/MMP-inhibitory activity, thus explaining the prolonged action following once daily administration. Finally, 84% of the intravenously administered cis-ACCP to rats was excreted intact in the urine.
• [EN] NEW CARBAMOYL-AND THIOCARBAMOYL-PHOSPHONATES AND PHARMACEUTICAL COMPOSITIONS COMPRISING THEM<br/>[FR] NOUVEAUX PHOSPHONATES DE CARBAMOYLE ET DE THIOCARBAMOYLE ET COMPOSITIONS PHARMACEUTIQUES LES COMPRENANT
  申请人：YISSUM RES DEV CO

  公开号：WO2004089962A3

  公开（公告）日：2005-07-21
• Electrochemically driven P–H oxidation and functionalization: synthesis of carbamoylphosphonates from phosphoramides and alcohols
  作者：Qiu-Li Wu、Xing-Guo Chen、Cong-De Huo、Xi-Cun Wang、Zheng-Jun Quan

  DOI：10.1039/c8nj05739g

  日期：——

  An electrochemical method to achieve carbamoylphosphonates from phosphoramides and alcohols via P–H oxidation and functionalization by using n-Bu4NI as a catalyst is reported. A series of carbamoylphosphonates were obtained with good to excellent yields under mild reaction conditions. The electrochemical reaction is carried out under constant current electrolysis, with the alcohol being used as a solvent

  据报道，使用n -Bu 4 NI作为催化剂，通过PH氧化和官能化反应，可从磷酰胺和醇中获得氨基甲酰基膦酸酯的电化学方法。在温和的反应条件下，以良好或优异的收率获得了一系列氨基甲酰基膦酸酯。电化学反应在恒定电流电解下进行，其中醇用作溶剂和底物，并且是有吸引力的绿色合成方法。