5,5-dimethyl-2-(2'-chloro-1'-hydroxy-1'-phenylethyl)-1,3,2-dioxaphosphorinane 2-oxide

• 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: 5,5-dimethyl-2-(2'-chloro-1'-hydroxy-1'-phenylethyl)-1,3,2-dioxaphosphorinane 2-oxide
• 英文别名: (1R)-2-chloro-1-(5,5-dimethyl-2-oxo-1,3,2lambda5-dioxaphosphinan-2-yl)-1-phenylethanol；(1R)-2-chloro-1-(5,5-dimethyl-2-oxo-1,3,2λ5-dioxaphosphinan-2-yl)-1-phenylethanol
• 化学式: C₁₃H₁₈ClO₄P
• 分子量: 304.71
• InChiKey: BPBYYYANEBJDHD-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,2-二甲基-1,3-丙二醇 在 奎宁 、 三氯化磷 作用下， 以 乙醇 、 甲苯 为溶剂， 生成 5,5-dimethyl-2-(2'-chloro-1'-hydroxy-1'-phenylethyl)-1,3,2-dioxaphosphorinane 2-oxide
  参考文献：
  名称：

  Synthesis and biological evaluation of α-hydroxyalkylphosphonates as new antimicrobial agents

  摘要：

  A set of alpha-quaternary 3-chloro-1-hydroxyalkylphosphonates, analogues of fosfomycin and fosfonochlorin, some of which are new compounds, was synthesized. The compounds were screened for bioactivity against several clinical and standard microbial isolates. Some were found to have moderate activity. The activity was higher with phenyl protection of the phosphoryl ester groups and alpha-phenyl substitution. Compound 11 was as effective or more potent than fosfomycin or chloramphenicol against several Gram-negative bacteria as well as against some Gram-positive ones. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.002

文献信息

• Organocatalyzed Synthesis of Tertiary α-Hydroxyphosphonates by a Highly Regioselective Modified Pudovik Reaction
  作者：Maria Teresa Barros、Ana Maria Faísca Phillips

  DOI：10.1002/ejoc.201100308

  日期：2011.7

  An organocatalytic modified Pudovik reaction between dialkyl or diaryl phosphites and α-haloketones was used to synthesize β-chloro-α-hydroxyphosphonates in high yields with very high regioselectivity and high stereoselectivity. Aliphatic, aromatic, and cyclic ketones could be used successfully. Under the optimized conditions it was possible to obtain enantiomerically enriched products with a combination

  使用二烷基或二芳基亚磷酸酯与 α-卤代酮之间的有机催化改性 Pudovik 反应以高产率合成 β-氯-α-羟基膦酸酯，具有非常高的区域选择性和高立体选择性。可以成功使用脂肪族、芳香族和环状酮。在优化条件下，可以通过奎宁和化学计量外消旋碱的组合获得对映异构体富集的产物，但 ee 值仅上升至 40%。β-氯官能团的存在允许进一步合成所获得的羟基膦酸酯，这可用于靶向合成，因为这些化合物通常具有重要的生物活性。
• Synthesis and biological evaluation of α-hydroxyalkylphosphonates as new antimicrobial agents
  作者：Ana Maria Faísca Phillips、Maria Teresa Barros、Marta Pacheco、Ricardo Dias

  DOI：10.1016/j.bmcl.2013.12.002

  日期：2014.1

  A set of alpha-quaternary 3-chloro-1-hydroxyalkylphosphonates, analogues of fosfomycin and fosfonochlorin, some of which are new compounds, was synthesized. The compounds were screened for bioactivity against several clinical and standard microbial isolates. Some were found to have moderate activity. The activity was higher with phenyl protection of the phosphoryl ester groups and alpha-phenyl substitution. Compound 11 was as effective or more potent than fosfomycin or chloramphenicol against several Gram-negative bacteria as well as against some Gram-positive ones. (C) 2013 Elsevier Ltd. All rights reserved.