dibenzyl 3-phenylpropylphosphonate | 82180-50-5

• 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: dibenzyl 3-phenylpropylphosphonate
• 英文别名: Dibenzyl (3-phenylpropyl)phosphonate；3-bis(phenylmethoxy)phosphorylpropylbenzene
• CAS: 82180-50-5
• 化学式: C₂₃H₂₅O₃P
• 分子量: 380.423
• InChiKey: KSFSXTMIEOWJIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  dibenzyl 3-phenylpropylphosphonate 在 palladium on activated charcoal 草酰氯 、 氢气 、 potassium carbonate 、 N,N-二甲基甲酰胺 、 sodium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丁酮 为溶剂， 反应 6.5h， 生成 N-[hydroxy(3-phenylpropyl)phosphinyl]-L-glutamic acid tripotassium salt
  参考文献：
  名称：

  Probing for a hydrophobic a binding register in prostate-specific membrane antigen with phenylalkylphosphonamidates

  摘要：

  To explore for the existence of an auxiliary hydrophobic binding register remote from the active site of PSMA a series of phenylalkylphosphonamidate derivatives of glutamic acid were synthesized and evaluated for their inhibitory potencies against PSMA. Both the phenyl- and benzylphosphonamidates (1a and 1b) exhibited only modest inhibitory potency against. The phenethyl analog 1c was intermediate in inhibitory potency while inhibitors possessing a longer alkyl tether from the phenyl ring, resulted in markedly improved K-i values. The greatest inhibitory potency was obtained for the inhibitors in which the phenyl ring was extended furthest from the central phosphorus (if, n = 5 and I g, n = 6). The slightly serrated pattern that emerged as the alkyl tether increased from three to six methylene units suggests that inhibitory potency is not simply correlated to increased hydrophobicity imparted by the phenylalkyl chain, but rather that one or more hydrophobic binding registers may exist remote from the substrate recognition architecture in the active site of PSMA. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.06.031
• 作为产物：
  描述：

  亚磷酸二苄酯 、 1-溴-3-苯基丙烷 在 四丁基碘化铵 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 74.0h， 以65%的产率得到dibenzyl 3-phenylpropylphosphonate
  参考文献：
  名称：

  Mild and efficient Cs2CO3-promoted synthesis of phosphonates

  摘要：

  mild and convenient synthesis for phosphonates using cesium carbonate (Cs2CO3), tetrabutylammonium iodide (TBAI) and DMF was developed at room temperature. Numerous dialkyl phosphites were screened using a diverse array of alkyl halides and these reaction conditions were found to be highly efficient producing various phosphonates exclusively in moderate to high yields. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.045

文献信息

• Mild and efficient Cs2CO3-promoted synthesis of phosphonates
  作者：Richard J Cohen、Daniel L Fox、Jarrod F Eubank、Ralph Nicholas Salvatore

  DOI：10.1016/j.tetlet.2003.09.045

  日期：2003.11

  mild and convenient synthesis for phosphonates using cesium carbonate (Cs2CO3), tetrabutylammonium iodide (TBAI) and DMF was developed at room temperature. Numerous dialkyl phosphites were screened using a diverse array of alkyl halides and these reaction conditions were found to be highly efficient producing various phosphonates exclusively in moderate to high yields. (C) 2003 Elsevier Ltd. All rights reserved.
• Probing for a hydrophobic a binding register in prostate-specific membrane antigen with phenylalkylphosphonamidates
  作者：Jack Maung、Jeremy P. Mallari、Teri A. Girtsman、Lisa Y. Wu、Jennifer A. Rowley、Nicholas M. Santiago、Alan N. Brunelle、Clifford E. Berkman

  DOI：10.1016/j.bmc.2004.06.031

  日期：2004.9

  To explore for the existence of an auxiliary hydrophobic binding register remote from the active site of PSMA a series of phenylalkylphosphonamidate derivatives of glutamic acid were synthesized and evaluated for their inhibitory potencies against PSMA. Both the phenyl- and benzylphosphonamidates (1a and 1b) exhibited only modest inhibitory potency against. The phenethyl analog 1c was intermediate in inhibitory potency while inhibitors possessing a longer alkyl tether from the phenyl ring, resulted in markedly improved K-i values. The greatest inhibitory potency was obtained for the inhibitors in which the phenyl ring was extended furthest from the central phosphorus (if, n = 5 and I g, n = 6). The slightly serrated pattern that emerged as the alkyl tether increased from three to six methylene units suggests that inhibitory potency is not simply correlated to increased hydrophobicity imparted by the phenylalkyl chain, but rather that one or more hydrophobic binding registers may exist remote from the substrate recognition architecture in the active site of PSMA. (C) 2004 Elsevier Ltd. All rights reserved.