dimethyl 2-oxo-3-(m-methylphenoxy)propylphosphonate | 40666-12-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: dimethyl 2-oxo-3-(m-methylphenoxy)propylphosphonate
• 英文别名: Dimethyl-2-oxo-3-(m-tolyloxy)-propylphosphat；Dimethyl (2-oxo-3-(m-tolyloxy)propyl)phosphonate；1-dimethoxyphosphoryl-3-(3-methylphenoxy)propan-2-one
• CAS: 40666-12-4
• 化学式: C₁₂H₁₇O₅P
• 分子量: 272.238
• InChiKey: TVMKJAJNZJMJHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl 2-oxo-3-(m-methylphenoxy)propylphosphonate 在 sodium hydride 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  N-(Methanesulfonyl)-16-phenoxyprostaglandin carboxamides: tissue-selective, uterine stimulants

  摘要：

  In an effort to develop tissue-selective prostaglandin analogues resistant to the metabolic inactivating pathways of the natural materials, hybrid compounds modified both at C-1 with a sulfonimide moiety and in the n-amylcarbinol side chain with substituted phenoxy groups were synthesized and evaluated in a variety of in vitro models. Several of these analogues exhibited potent, tissue-selective, uterine stimulant activity, a finding subsequently confirmed in clinical studies with one member of this series, N-(methanesulfonyl)-16-phenoxy-omega-tetranor-PGE2-carboxamide (CP-34089/ZK-57671, sulprostone).

  DOI：

  10.1021/jm00143a018
• 作为产物：
  描述：

  m-tolyloxyacetic acid methyl ester 、 甲基膦酸二甲酯 生成 dimethyl 2-oxo-3-(m-methylphenoxy)propylphosphonate
  参考文献：
  名称：

  BINDRA, J. S.;EGGLER, J. F.;JOHNSON, M. R.;SCHAAF, T. K.

  摘要：

  DOI：

文献信息

• BINDRA, J. S.;EGGLER, J. F.;JOHNSON, M. R.;SCHAAF, T. K.
  作者：BINDRA, J. S.、EGGLER, J. F.、JOHNSON, M. R.、SCHAAF, T. K.

  DOI：——

  日期：——
• US3985791A
  申请人：——

  公开号：US3985791A

  公开（公告）日：1976-10-12
• N-(Methanesulfonyl)-16-phenoxyprostaglandin carboxamides: tissue-selective, uterine stimulants
  作者：Thomas K. Schaaf、Jasjit S. Bindra、James F. Eggler、Jacob J. Plattner、A. James Nelson、M. Ross Johnson、Jay W. Constantine、Hans-Juergen Hess、Walter Elger

  DOI：10.1021/jm00143a018

  日期：1981.11

  In an effort to develop tissue-selective prostaglandin analogues resistant to the metabolic inactivating pathways of the natural materials, hybrid compounds modified both at C-1 with a sulfonimide moiety and in the n-amylcarbinol side chain with substituted phenoxy groups were synthesized and evaluated in a variety of in vitro models. Several of these analogues exhibited potent, tissue-selective, uterine stimulant activity, a finding subsequently confirmed in clinical studies with one member of this series, N-(methanesulfonyl)-16-phenoxy-omega-tetranor-PGE2-carboxamide (CP-34089/ZK-57671, sulprostone).