cholesteryl N-(2-bromoethyl)-N,P-dimethylphosphonamidate | 733037-61-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: cholesteryl N-(2-bromoethyl)-N,P-dimethylphosphonamidate
• 英文别名: 2-bromo-N-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy-methylphosphoryl]-N-methylethanamine
• CAS: 733037-61-1
• 化学式: C₃₁H₅₅BrNO₂P
• 分子量: 584.661
• InChiKey: CUJFAIQGFHDFGE-IRUPBOBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  三甲胺 、 cholesteryl N-(2-bromoethyl)-N,P-dimethylphosphonamidate 以 苯 为溶剂， 反应 12.0h， 以42%的产率得到2-[[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy-methylphosphoryl]-methylamino]ethyl-trimethylazanium;bromide
  参考文献：
  名称：

  Cationic Amphiphiles of Methylphosphonates and Cholesterol Phosphocholines and Their Homo Derivatives

  摘要：

  A method of synthesis of (P-->O) and (P-->N)-choline cholesteryl methylphosphonates and their homo derivatives of the cationic type is developed. These compounds were obtained by the Arbuzov reaction between bromomethane and cyclic cholesteryl phosphorous esters and amidoesters and subsequent aminolysis of the intermediate bromoalkyl phosphonates. Alkylation of trimethylamine with cholesteryl ethanediyl and propanediyl phosphates gives cholesterol phosphocholines and their homo derivatives.

  DOI：

  10.1023/b:rugc.0000016015.55496.b9
• 作为产物：
  描述：

  胆固醇 、 alkaline earth salt of/the/ methylsulfuric acid 以 苯 为溶剂， 反应 8.0h， 生成 cholesteryl N-(2-bromoethyl)-N,P-dimethylphosphonamidate
  参考文献：
  名称：

  Cationic Amphiphiles of Methylphosphonates and Cholesterol Phosphocholines and Their Homo Derivatives

  摘要：

  A method of synthesis of (P-->O) and (P-->N)-choline cholesteryl methylphosphonates and their homo derivatives of the cationic type is developed. These compounds were obtained by the Arbuzov reaction between bromomethane and cyclic cholesteryl phosphorous esters and amidoesters and subsequent aminolysis of the intermediate bromoalkyl phosphonates. Alkylation of trimethylamine with cholesteryl ethanediyl and propanediyl phosphates gives cholesterol phosphocholines and their homo derivatives.

  DOI：

  10.1023/b:rugc.0000016015.55496.b9