diethyl (1-phenyl-1-propylaminoeth-1-yl)phosphonate

• 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: diethyl (1-phenyl-1-propylaminoeth-1-yl)phosphonate
• 英文别名: N-[1-phenyl-1-(diethoxyphosphoryl)ethyl]-N-propylamine；N-(1-diethoxyphosphoryl-1-phenylethyl)propan-1-amine
• 化学式: C₁₅H₂₆NO₃P
• 分子量: 299.35
• InChiKey: YIFMELXHUUASRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  正丙胺 、 二乙基亚磷酸氢酯 、 苯乙酮 在 盐酸 、 sodium sulfate 作用下， 反应 96.0h， 以29%的产率得到diethyl (1-phenyl-1-propylaminoeth-1-yl)phosphonate
  参考文献：
  名称：

  Synthesis and 31 P NMR characterization of new low toxic highly sensitive pH probes designed for in vivo acidic pH studies

  摘要：

  With the aim to provide sensitive P-31 NMR probes of intra- and extracellular pH gradients that may reach cellular acidic compartments in biological systems, new 7-aminophosphonates were designed to meet basic requirements such as a low pK(a)s and a great chemical difference (Deltadelta(ab)) between the limiting P-31 NMR chemical shifts in acidic (delta(a)) and basic (delta(b)) media. A series of six phosphorylated pyrrolidines and linear aminophosphonates were synthesized using aminophosphorylation reactions and were screened for cytotoxicity on cultured Muller cells. Among the compounds not being toxic under these conditions. three molecules were selected since they displayed the best in vitro (in several phosphate buffers and in a cytosol-like solution) properties as P-31 NMR acidic pH markers. that is 3, 5 and 9, having the pK(a) values of 3.63, 5.89 and 5.66, respectively. The Deltadelta(ab) values of these pH markers were at least 3 times larger than that of standard P-31 NMR probes, with a low sensitivity to ionic strength changes. From these data. it was proposed that 3, 5 and 9 could be used as reporting probes of subtle proton movements in acidic compartments, an area that still remains poorly investigated using non invasive IT NMR methods. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00414-x

文献信息

• ３１ＰＮＭＲにおけるｐＨマーカーとしてのアミノホスホネートの使用
  申请人：——

  公开号：JP2002506871A

  公开（公告）日：2002-03-05

  \n (57)【要約】\n本発明は、Ｒ１、Ｒ２、Ｒ３、Ｒ、Ｒ’１、Ｒ’２、Ｒ’３、Ｒ’が請求項１および８のように定義される式（Ｉ．１）および（Ｉ．２）に記載の化合物に関する。本発明は、また、Ｒ１、Ｒ２、Ｒ３、Ａ、ｐ、Ｒ、Ｔ１、Ｔ２、Ｒ’１、Ｒ’２、Ｒ’３、Ａ’、ｐ’、Ｒ’、Ｔ’１、Ｔ’２が請求項１３および２３のように定義される式（ＩＩ．１）および（ＩＩ．２）に記載のアミノホスホネートの、３１Ｐ ＮＭＲ ｐＨインジケーターとしての使用にも関する。\n

  \(57) [摘要] Ϯn本发明涉及根据式（I.1）和（I.2）的化合物，其中 R1、R2、R3、R、R'1、R'2、R'3 和 R' 的定义如权利要求 1 和 8 所述。有关。本发明还涉及式 (I.1) 和 (I.2) 的化合物，其中 R1、R2、R3、A、p、R、T1、T2、R'1、R'2、R'3、A'、p'、R'、T'1、T'2 的定义如权利要求 13 和 23 所述，还涉及根据式 (II.1) 和 (II.2) 的氨基膦酸盐作为 31P NMR pH 指示剂的用途。\n
• UTILISATION D'AMINOPHOSPHONATES COMME MARQUEURS DE PH EN RMN DU 31 P
  申请人：CENTRE NATIONAL DELA RECHERCHE SCIENTIFIQUE (CNRS)

  公开号：EP1064287A1

  公开（公告）日：2001-01-03
• US6528656B1
  申请人：——

  公开号：US6528656B1

  公开（公告）日：2003-03-04
• [EN] USE OF AMINOPHOSPHONATES AS<31>P NMR pH INDICATORS<br/>[FR] UTILISATION D'AMINOPHOSPHONATES COMME MARQUEURS DE pH EN RMN DU <31>P
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (CN RS)

  公开号：WO1999047527A1

  公开（公告）日：1999-09-23

  (EN) The invention concerns compounds of formula (I.1) and (I.2) wherein R1, R2, R3, R, R'1, R'2, R'3, R' are such as defined in Claims 1 and 8. The invention also concerns the use of aminophosphonates of formula (II.1) and (II.2) wherein R1, R2, R3, A, p, R, T1, T2, R'1, R'2, R'3, A', p', R', T'1, T'2 such as defined in Claims 13 and 23, as 31P NMR pH indicators.(FR) La présente invention concerne des composés de formules (I.1) et (I.2), dans lesquelles R1, R2, R3, R, R'1, R'2, R'3 et R' sont tels que définis aux revendications 1 et 8. L'invention se rapporte par ailleurs à l'utilisation d'aminophosphonates de formules (II.1) et (II.2), dans lesquelles R1, R2, R3, A, p, R, T1, T2, R'1, R'2, R'3, A', p', R', T'1 et T'2 sont tels que définis aux revendications 13 et 23, comme marqueurs du pH en RMN du 31P.
• Synthesis and 31 P NMR characterization of new low toxic highly sensitive pH probes designed for in vivo acidic pH studies
  作者：Sophie Martel、Jean-Louis Clément、Agnès Muller、Marcel Culcasi、Sylvia Pietri

  DOI：10.1016/s0968-0896(01)00414-x

  日期：2002.5

  With the aim to provide sensitive P-31 NMR probes of intra- and extracellular pH gradients that may reach cellular acidic compartments in biological systems, new 7-aminophosphonates were designed to meet basic requirements such as a low pK(a)s and a great chemical difference (Deltadelta(ab)) between the limiting P-31 NMR chemical shifts in acidic (delta(a)) and basic (delta(b)) media. A series of six phosphorylated pyrrolidines and linear aminophosphonates were synthesized using aminophosphorylation reactions and were screened for cytotoxicity on cultured Muller cells. Among the compounds not being toxic under these conditions. three molecules were selected since they displayed the best in vitro (in several phosphate buffers and in a cytosol-like solution) properties as P-31 NMR acidic pH markers. that is 3, 5 and 9, having the pK(a) values of 3.63, 5.89 and 5.66, respectively. The Deltadelta(ab) values of these pH markers were at least 3 times larger than that of standard P-31 NMR probes, with a low sensitivity to ionic strength changes. From these data. it was proposed that 3, 5 and 9 could be used as reporting probes of subtle proton movements in acidic compartments, an area that still remains poorly investigated using non invasive IT NMR methods. (C) 2002 Elsevier Science Ltd. All rights reserved.