dimethyl (1-phenyl-4-bromobutyl)phosphonate | 137333-80-3

• 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: dimethyl (1-phenyl-4-bromobutyl)phosphonate
• 英文别名: (4-bromo-1-dimethoxyphosphorylbutyl)benzene
• CAS: 137333-80-3
• 化学式: C₁₂H₁₈BrO₃P
• 分子量: 321.151
• InChiKey: GYXGRTGIIFOMOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  17.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  dimethyl (1-phenyl-4-bromobutyl)phosphonate 在 三甲基溴硅烷 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 36.0h， 生成 1-(4-phenyl-4-phosphonobut-1-yl)cytosine
  参考文献：
  名称：

  Photo-Arbuzov rearrangement route to acyclic nucleoside benzylphosphonates

  摘要：

  The recently discovered photo-Arbuzov rearrangement was carried out with a series of tert-butyldimethyl-silyl-protected dimethyl benzyl phosphites, 9, 15, 18, 20, and 22, easily derived from alcohol precursors, to afford the corresponding dimethyl benzylphosphonates in 67-74% isolated yields. One of the phosphonates, 10, was further converted to the primary bromide which underwent reaction with the sodium salts of adenine, cytosine, and 2-amino-6-chloropurine to give the desired N-alkylated acyclic nucleoside dimethyl benzylphosphonates. The 2-amino-6-chloro compound was further elaborated to the guaninyl and 2,6-diamino derivatives. Demethylation afforded the acyclic nucleoside-based benzylphosphonic acids 25, 27, 29, 31, and 32 in good overall yields. These molecules are closely related structurally to the active antiviral 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA) and the potent human erythrocyte purine nucleoside phosphorylase (PNP) inhibitors 9-(5-phosphonopentyl)guanine and 9-(5,5-difluoro-5-phosphonopentyl)guanine.

  DOI：

  10.1021/jo00026a008
• 作为产物：
  描述：

  3-苯丙烯溴酸酯 在 吡啶 、 四氮唑 、 lithium aluminium tetrahydride 、 四溴化碳 、 四丁基氟化铵 、 三苯基膦 作用下， 以 四氢呋喃 、 乙腈 、 苯 为溶剂， 反应 68.0h， 生成 dimethyl (1-phenyl-4-bromobutyl)phosphonate
  参考文献：
  名称：

  Photo-Arbuzov rearrangement route to acyclic nucleoside benzylphosphonates

  摘要：

  The recently discovered photo-Arbuzov rearrangement was carried out with a series of tert-butyldimethyl-silyl-protected dimethyl benzyl phosphites, 9, 15, 18, 20, and 22, easily derived from alcohol precursors, to afford the corresponding dimethyl benzylphosphonates in 67-74% isolated yields. One of the phosphonates, 10, was further converted to the primary bromide which underwent reaction with the sodium salts of adenine, cytosine, and 2-amino-6-chloropurine to give the desired N-alkylated acyclic nucleoside dimethyl benzylphosphonates. The 2-amino-6-chloro compound was further elaborated to the guaninyl and 2,6-diamino derivatives. Demethylation afforded the acyclic nucleoside-based benzylphosphonic acids 25, 27, 29, 31, and 32 in good overall yields. These molecules are closely related structurally to the active antiviral 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA) and the potent human erythrocyte purine nucleoside phosphorylase (PNP) inhibitors 9-(5-phosphonopentyl)guanine and 9-(5,5-difluoro-5-phosphonopentyl)guanine.

  DOI：

  10.1021/jo00026a008

文献信息

• Photo-Arbuzov rearrangement route to acyclic nucleoside benzylphosphonates
  作者：Khairuzzaman B. Mullah、Wesley G. Bentrude

  DOI：10.1021/jo00026a008

  日期：1991.12

  The recently discovered photo-Arbuzov rearrangement was carried out with a series of tert-butyldimethyl-silyl-protected dimethyl benzyl phosphites, 9, 15, 18, 20, and 22, easily derived from alcohol precursors, to afford the corresponding dimethyl benzylphosphonates in 67-74% isolated yields. One of the phosphonates, 10, was further converted to the primary bromide which underwent reaction with the sodium salts of adenine, cytosine, and 2-amino-6-chloropurine to give the desired N-alkylated acyclic nucleoside dimethyl benzylphosphonates. The 2-amino-6-chloro compound was further elaborated to the guaninyl and 2,6-diamino derivatives. Demethylation afforded the acyclic nucleoside-based benzylphosphonic acids 25, 27, 29, 31, and 32 in good overall yields. These molecules are closely related structurally to the active antiviral 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA) and the potent human erythrocyte purine nucleoside phosphorylase (PNP) inhibitors 9-(5-phosphonopentyl)guanine and 9-(5,5-difluoro-5-phosphonopentyl)guanine.