(1,1'-biphenyl-4-yl)methylphosphinic acid | 860292-38-2

• 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: (1,1'-biphenyl-4-yl)methylphosphinic acid
• 英文别名: 4-phenylbenzyl-H-phosphinic acid；(4-Phenylphenyl)methylphosphinic acid
• CAS: 860292-38-2
• 化学式: C₁₃H₁₃O₂P
• 分子量: 232.219
• InChiKey: QETRTGXQYPUVJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  43.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1,1'-biphenyl-4-yl)methylphosphinic acid 在 1-羟基苯并三唑 、 一水合肼 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 21.0h， 生成 1-[(benzyloxy)carbonyl]prolyl-N1-({[(1,1'-biphenyl-4-yl)methyl](methoxy)phosphoryl}methyl)leucinamide
  参考文献：
  名称：

  Design, modelling, synthesis and biological evaluation of peptidomimetic phosphinates as inhibitors of matrix metalloproteinases MMP-2 and MMP-8

  摘要：

  Three novel peptidomimetic phosphinate inhibitors have been synthesized and evaluated as inhibitors of matrix metalloprotemases MMP-2 and MMP-8. Their IC50 values are in the micromolar range, and one of them showed to be the most effective inhibitor of MMP-2. The differences in binding affinities for MMP-2 and MMP-8 of the three phosphinates have been rationalized by means of modelling studies and molecular dynamics simulations. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.079
• 作为产物：
  描述：

  4-(碘甲基)联苯 在 二(三甲基硅烷基)亚膦酸酯 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以70%的产率得到(1,1'-biphenyl-4-yl)methylphosphinic acid
  参考文献：
  名称：

  Design, modelling, synthesis and biological evaluation of peptidomimetic phosphinates as inhibitors of matrix metalloproteinases MMP-2 and MMP-8

  摘要：

  Three novel peptidomimetic phosphinate inhibitors have been synthesized and evaluated as inhibitors of matrix metalloprotemases MMP-2 and MMP-8. Their IC50 values are in the micromolar range, and one of them showed to be the most effective inhibitor of MMP-2. The differences in binding affinities for MMP-2 and MMP-8 of the three phosphinates have been rationalized by means of modelling studies and molecular dynamics simulations. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.079

文献信息

• Green, Palladium-Catalyzed Synthesis of Benzylic<i>H</i>-Phosphinates from Hypophosphorous Acid and Benzylic Alcohols
  作者：Laëtitia Coudray、Jean-Luc Montchamp

  DOI：10.1002/ejoc.200800581

  日期：2008.8

  Benzylic alcohols cross-couple directly with concentrated H(3)PO(2) using Pd/xantphos (1 or 2 mol-%). Depending on the substrate, DMF at 110 degrees C, or t-AmOH at reflux with a Dean-Stark trap, can be used. A broad range of benzylic alcohols reacted successfully in moderate to good yields. The preparation of other organophosphorus compounds (phosphinic and phosphonic acids) is also demonstrated.Asymmetric

  苯甲醇直接与使用Pd / xantphos（1或2 mol％）的浓缩H（3）PO（2）交叉偶联。根据基材的不同，可以使用110摄氏度的DMF或带有迪安-斯达克榻分水器的t-AmOH回流。各种各样的苄醇以中等到良好的收率成功反应。还证明了其他有机磷化合物（次膦酸和膦酸）的制备。与（R）-1-（2-萘基）乙醇的不对称反应提供了77％ee的相应H-次膦酸。该方法提供了绿色，不含PC1（3）的苄基-H-次膦酸入口。