(1-amino-1-methyl-ethyl)-phosphonic acid diethyl ester | 16814-09-8

• 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: (1-amino-1-methyl-ethyl)-phosphonic acid diethyl ester
• 英文别名: diethyl (1-amino-1-methylethyl)phosphonate；diethyl 1-methyl-1-aminoethylphosphonate；diethyl (2-aminopropan-2-yl)phosphonate；diethyl 2-aminopropan-2-ylphosphonate；(α-amino-isopropyl)-phosphonic acid diethyl ester；(α-Amino-isopropyl)-phosphonsaeure-diaethylester；2-diethoxyphosphorylpropan-2-amine
• CAS: 16814-09-8
• 化学式: C₇H₁₈NO₃P
• 分子量: 195.199
• InChiKey: PMMYNQBSYRNMOU-UHFFFAOYSA-N

物化性质

• 沸点：
  65-66 °C(Press: 3 Torr)
• 密度：
  1.0437 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1-amino-1-methyl-ethyl)-phosphonic acid diethyl ester 在 甲苯 作用下， 生成 [α-(N'-phenyl-ureido)-isopropyl]-phosphonic acid diethyl ester
  参考文献：
  名称：

  Medwed'; Kabatschnik, Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1956, p. 684,690;engl.Ausg.S.695,700

  摘要：

  DOI：
• 作为产物：
  描述：

  diethyl 1-methyl-1-aminoethylphosphonate oxalate 在 碳酸氢钠 作用下， 以 水 为溶剂， 生成 (1-amino-1-methyl-ethyl)-phosphonic acid diethyl ester
  参考文献：
  名称：

  Synthesis and solution studies of Cu(II) complexes with pyridine derivatives of iminobisphosphonic acids

  摘要：

  New 2-pyridyl, 3-pyridyl and 4-pyridyl derivatives of iminobisphosphonic acid were prepared by addition of tris(trimethylsilyl) phosphite to the corresponding derivatives of pyridineimine-methylphosphonates 3 and subsequent methanolysis of the silylated products 4. Solution studies on the coordination abilities of the ligands have shown that these compounds bind copper(II) ion through the tridentate {N,O,O} mode, where Cu(II) is stabilized by two five-membered chelate rings. The complexes obtained are very stable, with the pCu(II) value above 12, and therefore the ligands can be used as powerful chelating agents for copper ion. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2010.09.045

文献信息

• Synthesis and Biological Characterization of New Aminophosphonates for Mitochondrial pH Determination by ³¹P NMR Spectroscopy
  作者：Marcel Culcasi、Gilles Casano、Céline Lucchesi、Anne Mercier、Jean-Louis Clément、Valérie Pique、Laure Michelet、Anja Krieger-Liszkay、Maxime Robin、Sylvia Pietri

  DOI：10.1021/jm301866e

  日期：2013.3.28

  fibroblasts cell cultures. Of these, two selected compounds demonstrated to distribute at NMR detectable levels within the cytosolic and mitochondrial sites following their perfusion to isolated rat livers, with no detrimental effects on cell energetics and aerobic respiration. This study provided a new molecular scaffold for further development of in situ spectroscopic real-time monitoring of mitochondrion/cytosol

  设计并合成了一系列将二乙氧基磷酰基与烷基连接的三苯基溴化tail尾部结合的线粒体靶向α-氨基膦酸酯，并对其pH敏感的31 P NMR特性和体内外生物学活性进行了评估。结果表明，许多这些线粒体氨基膦酸酯的p K a值符合线粒体pH范围，短暂弛豫和与敏感的31相容的化学位移参数P NMR检测以及对绿藻和鼠成纤维细胞培养物的低细胞毒性。在这些化合物中，有两种选择的化合物在向分离的大鼠肝脏灌注后，在胞质和线粒体位点以NMR可检测的水平分布，对细胞能量和有氧呼吸没有有害影响。该研究为线粒体/细胞质pH梯度原位光谱实时监测的进一步发展提供了新的分子支架。
• On the vasoprotective mechanisms underlying novel β-phosphorylated nitrones: Focus on free radical characterization, scavenging and NO-donation in a biological model of oxidative stress
  作者：Mathieu Cassien、Consuelo Petrocchi、Sophie Thétiot-Laurent、Maxime Robin、Emilie Ricquebourg、Chouaib Kandouli、Alice Asteian、Antal Rockenbauer、Anne Mercier、Marcel Culcasi、Sylvia Pietri

  DOI：10.1016/j.ejmech.2016.04.067

  日期：2016.8

  featured an antioxidant moiety occurring in natural phenolic acids. From the experimental screening of these hydroxyphenyl- and methoxyphenyl-substituted PPNs, biocompatible nitrones 4d, and 4g−4i deriving from caffeic, gallic, ferulic and sinapic acids, which combined improved EPR probing of ROS formation, vasorelaxant action and antioxidant potency, might be potential drug candidate alternatives to PBN

  合成了一系列具有不同芳族取代基（PPN）的新型杂化2-（二乙氧基磷酰基）-N-（亚苄基）丙烷-2-氧化胺衍生物。评估了这些分子在11种不同自由基上的EPR自旋捕获潜力以及体外NO给予特性，对预收缩大鼠主动脉环的细胞毒性和血管保护作用。新PPN的一个亚家族具有天然酚酸中存在的抗氧化剂部分。通过对这些被羟基苯基和甲氧基苯基取代的PPN的实验筛选，生物相容性硝酮4d和4g - 4i 源自咖啡酸，没食子酸，阿魏酸和芥子酸的酸，结合改进的EPR探测ROS形成，血管舒张作用和抗氧化剂效能，可能是PBN及其类似物的潜在候选药物。
• Haloacylaminoalkylphosphonates
  申请人：Ciba-Geigy Corporation

  公开号：US04579691A1

  公开（公告）日：1986-04-01

  When applied as safeners, the haloacylaminoalkylphosphinates, haloacylaminoalkylphosphinates and haloacylaminoalkylphosphine oxides of the formula I below are able to protect cultivated plants from the phytotoxic effects of herbicides. Suitable crops are preferably sorghum, cereals, rice, maize and soya beans and the herbicides employed are chloroacetanilides and thiocarbamates. The haloacylaminoalkylphosphonates, haloacylaminoalkylphosphinates and haloacylaminoalkylphosphine oxides have the formula I ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.4 alkenyloxy, C.sub.2 -C.sub.4 alkynyloxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.8 alkoxyalkoxy or C.sub.1 -C.sub.4 cyanoalkoxy, R.sub.2 is hydrogen or a substituent as defined for R.sub.1, R.sub.3 and R.sub.4 are each independently hydrogen, C.sub.1 -C.sub.4 alkyl or one of R.sub.3 and R.sub.4 is also a radical ##STR2## or both taken together with the carbon atom to which they are attached are also a C.sub.3 -C.sub.11 cycloalkyl radical, R.sub.5 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 alkynyl, C.sub.2 -C.sub.8 alkoxyalkyl, C.sub.1 -C.sub.4 haloalkoxy or aralkyl, R.sub.6 is hydrogen or C.sub.1 -C.sub.4 alkyl, X.sub.1 and X.sub.2 are each independently halogen or one of X.sub.1 and X.sub.2 is also hydrogen, and n is 1, 2 or 3.

  当作为安全剂应用时，以下公式I中的卤代酰氨基烷基膦酸酯、卤代酰氨基烷基膦酸酯和卤代酰氨基烷基膦氧化物能够保护栽培植物免受除草剂的植物毒性影响。适合的作物主要是高粱、谷物、稻米、玉米和大豆，所使用的除草剂是氯乙基苯胺和硫代氨基甲酸酯。卤代酰氨基烷基膦酸酯、卤代酰氨基烷基膦酸酯和卤代酰氨基烷基膦氧化物具有以下公式I##STR1##其中R.sub.1是C.sub.1 -C.sub.4烷基、C.sub.1 -C.sub.4烷氧基、C.sub.2 -C.sub.4烯氧基、C.sub.2 -C.sub.4炔氧基、C.sub.1 -C.sub.4卤代烷基、C.sub.2 -C.sub.8烷氧基烷氧基或C.sub.1 -C.sub.4氰基烷氧基，R.sub.2是氢或类似R.sub.1定义的取代基，R.sub.3和R.sub.4分别独立地是氢、C.sub.1 -C.sub.4烷基或R.sub.3和R.sub.4中的一个也是基团##STR2##或者两者与它们连接的碳原子一起也是一个C.sub.3 -C.sub.11环烷基基团，R.sub.5是氢、C.sub.1 -C.sub.4烷基、C.sub.3 -C.sub.7环烷基、C.sub.2 -C.sub.4烯基、C.sub.2 -C.sub.4炔基、C.sub.2 -C.sub.8烷氧基烷基、C.sub.1 -C.sub.4卤代烷氧基或芳基烷基，R.sub.6是氢或C.sub.1 -C.sub.4烷基，X.sub.1和X.sub.2各自独立地是卤素或X.sub.1和X.sub.2中的一个也是氢，n为1、2或3。
• Mixed carboxylic - carbonic anhydride method in phosphono peptide synthesis
  作者：Paweł Kafarski、Barbara Lejczak

  DOI：10.1016/s0040-4020(01)89200-0

  日期：1989.1

  Factors influencing the reaction yields and formation of the side products during coupling of N-carbobenzoxyamino acids with dialkyl or diphenyl aminoalkylphosphonates, by means of mixed anhydride procedure, were evaluated. The recommended procedure, arising from these studies, involves the use of chloroform/ethyl chloroformate/triethylamine system and delicate warming of the reaction mixture during

  通过混合酸酐法，评估了在N-碳苯甲氧基氨基酸与二烷基或二苯基氨基烷基膦酸酯偶联过程中影响反应产率和副产物形成的因素。从这些研究中得出的推荐程序包括使用氯仿/氯甲酸乙酯/三乙胺系统，以及在偶联步骤中对反应混合物进行精细加热。
• STUDY ON THE KINETICS OF THE REACTION BETWEEN DIETHYL ESTER OF 1-AMINO-METHYL-ETHANEPHOSPHONIC ACID AND PHENYL ISOCYANATE
  作者：Alexi Alexiev、Victoria Lachkova、Galin Petrov

  DOI：10.1080/10426509708031574

  日期：1997.9

  of the reaction between O,O-diethyl ester of 1-amino-1-methyl-ethane phosphonic acid and phenylisocyanate, producing diethyl ester of 1-methyl-1-(N-phenylcarbamoyl-amino)ethane phosphonic acid is studied by IR spectroscopy. It is established that the reaction is of second order. The probable scheme of the reaction mechanism is suggested. The rate constant k of the initial stage of the reaction is determined

  摘要 研究了1-氨基-1-甲基-乙烷膦酸的O,O-二乙酯与异氰酸苯酯反应生成1-甲基-1-(N-苯基氨基甲酰基-氨基)乙烷膦酸二乙酯的动力学。通过红外光谱。确定反应是二级反应。提出了反应机理的可能方案。确定反应初始阶段的速率常数 k。已确定速率常数在过程的高级阶段增加。观察到的增强归因于反应产物的自催化作用。