O-ethyl-2-phenethylphosphonyl chloride | 88501-39-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: O-ethyl-2-phenethylphosphonyl chloride
• 英文别名: Ethyl (2-phenylethyl)phosphonochloridate；2-[chloro(ethoxy)phosphoryl]ethylbenzene
• CAS: 88501-39-7
• 化学式: C₁₀H₁₄ClO₂P
• 分子量: 232.647
• InChiKey: SSHIZRLPUAKKPR-UHFFFAOYSA-N

物化性质

• 沸点：
  312.3±35.0 °C(Predicted)
• 密度：
  1.179±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  O-ethyl-2-phenethylphosphonyl chloride 在 10percent Pd/C 氢气 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (3R)-N-hydroxy-2-[(R)-ethoxy(2-phenylethyl)phosphoryl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide
  参考文献：
  名称：

  New Type of Metalloproteinase Inhibitor:  Design and Synthesis of New Phosphonamide-Based Hydroxamic Acids

  摘要：

  A series of phosphonamide-based hydroxamate derivatives were synthesized, and the inhibitory activities were evaluated against various metalloproteinases in order to clarify its selectivity profile. Among the four diastereomeric isomers resulting from the chirality at the C-3 and P atoms, the compound with a (R,R)-configuration both at the C-3 position and the phosphorus atom was found to be potently active, while the other diastereomeric isomers were almost inactive. A number of (R,R)-compounds synthesized here exhibited broad spectrum activities with nanomolar K-i values against MMP-1, -3, -9, and TACE and also showed nanomolar IC50 values against HB-EGF shedding in a cell-based inhibition assay. The modeling study using X-ray structure of MMP-3 suggested the possible binding mode of the phosphonamide-based inhibitors.

  DOI：

  10.1021/jm0103211
• 作为产物：
  描述：

  2-苯基乙基磷酸二乙酯 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 生成 O-ethyl-2-phenethylphosphonyl chloride
  参考文献：
  名称：

  New Type of Metalloproteinase Inhibitor:  Design and Synthesis of New Phosphonamide-Based Hydroxamic Acids

  摘要：

  A series of phosphonamide-based hydroxamate derivatives were synthesized, and the inhibitory activities were evaluated against various metalloproteinases in order to clarify its selectivity profile. Among the four diastereomeric isomers resulting from the chirality at the C-3 and P atoms, the compound with a (R,R)-configuration both at the C-3 position and the phosphorus atom was found to be potently active, while the other diastereomeric isomers were almost inactive. A number of (R,R)-compounds synthesized here exhibited broad spectrum activities with nanomolar K-i values against MMP-1, -3, -9, and TACE and also showed nanomolar IC50 values against HB-EGF shedding in a cell-based inhibition assay. The modeling study using X-ray structure of MMP-3 suggested the possible binding mode of the phosphonamide-based inhibitors.

  DOI：

  10.1021/jm0103211

文献信息

• 一种α,β-不饱和膦酰胺类化合物的制备方法
  申请人：北京化工大学

  公开号：CN114560888A

  公开（公告）日：2022-05-31

  本发明提供了一种α,β‑不饱和膦酰胺类化合物的制备方法。膦酰氯类化合物与亚胺类化合物反应，在碱存在下反应得到反式构型的α,β‑不饱和膦酰胺类化合物。亚胺可以通过醛和胺原位反应制备，该制备方法原料简单易得，操作方便。所得到的化合物可应用于重要的有机材料和抑制剂类药物以及农药，还可以用于有机材料和药物合成中间体，用于多种材料和药物制备。
• New Type of Metalloproteinase Inhibitor:  Design and Synthesis of New Phosphonamide-Based Hydroxamic Acids
  作者：Masaaki Sawa、Takao Kiyoi、Kiriko Kurokawa、Hiroshi Kumihara、Minoru Yamamoto、Tomohiro Miyasaka、Yasuko Ito、Ryoichi Hirayama、Tomomi Inoue、Yasuyuki Kirii、Eiji Nishiwaki、Hiroshi Ohmoto、Yu Maeda、Etsuko Ishibushi、Yoshimasa Inoue、Kohichiro Yoshino、Hirosato Kondo

  DOI：10.1021/jm0103211

  日期：2002.2.1

  A series of phosphonamide-based hydroxamate derivatives were synthesized, and the inhibitory activities were evaluated against various metalloproteinases in order to clarify its selectivity profile. Among the four diastereomeric isomers resulting from the chirality at the C-3 and P atoms, the compound with a (R,R)-configuration both at the C-3 position and the phosphorus atom was found to be potently active, while the other diastereomeric isomers were almost inactive. A number of (R,R)-compounds synthesized here exhibited broad spectrum activities with nanomolar K-i values against MMP-1, -3, -9, and TACE and also showed nanomolar IC50 values against HB-EGF shedding in a cell-based inhibition assay. The modeling study using X-ray structure of MMP-3 suggested the possible binding mode of the phosphonamide-based inhibitors.