(3-aminopropyl)phosphoramidic acid diisopropyl ester | 919512-60-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: (3-aminopropyl)phosphoramidic acid diisopropyl ester
• 英文别名: Bis(1-methylethyl) N-(3-aminopropyl)phosphoramidate；N'-di(propan-2-yloxy)phosphorylpropane-1,3-diamine
• CAS: 919512-60-0
• 化学式: C₉H₂₃N₂O₃P
• 分子量: 238.267
• InChiKey: ZHRUSMHKSFBSSV-UHFFFAOYSA-N

物化性质

• 沸点：
  297.3±42.0 °C(Predicted)
• 密度：
  1.048±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  73.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3-aminopropyl)phosphoramidic acid diisopropyl ester 、 Ethyl 4-chloro-1,3-diphenylpyrazolo<3,4-b>pyridine-5-carboxylate 以 四氢呋喃 为溶剂， 以69%的产率得到diisopropyl 3-[5-(ethoxycarbonyl)-1,3-diphenyl-1H-pyrazolo[3,4-b]pyridin-4-ylamino]propylphosphoramidate
  参考文献：
  名称：

  新型1H-吡唑并[3,4-b]吡啶氨基磷酸酯衍生物的合成与表征

  摘要：

  十二个新的 1 H-吡唑并 [3,4-b] 吡啶氨基磷酸酯衍生物在温和条件下通过氨基烷基氨基磷酸酯在 4-Cl 取代的吡唑并 [3,4-b] 吡啶上的亲核芳香取代反应以良好的产率合成。新化合物通过红外、 1 H、 13 C 和 31 P NMR 光谱和 HRMS 进行了表征。一种化合物的晶体结构通过 X 射线衍射解析，并显示出涉及氨基磷酸酯基团的分子间相互作用网络。

  DOI：

  10.3998/ark.5550190.p008.413
• 作为产物：
  描述：

  亚磷酸二异丙酯 、 1,3-丙二胺 以 四氯化碳 、 乙醇 为溶剂， 以53%的产率得到(3-aminopropyl)phosphoramidic acid diisopropyl ester
  参考文献：
  名称：

  Porphyrin - Phosphoramidate Conjugates: Synthesis, Photostability and Singlet Oxygen Generation

  摘要：

  中-四(五氟苯基)卟啉与氨基烷基磷酰胺发生反应，生成在中-芳基的 4 位上被一个或四个磷酰胺基团取代的卟啉。新的卟啉衍生物具有很高的光稳定性，其中一些比中-四（1-甲基吡啶鎓-4-基）卟啉（一种众所周知的优良单线态氧生成物）具有更好的单线态氧生成能力。

  DOI：

  10.1071/ch11013

文献信息

• Porphyrin - Phosphoramidate Conjugates: Synthesis, Photostability and Singlet Oxygen Generation
  作者：Leandro F. Pedrosa、Marcos C. de Souza、Maria A. F. Faustino、Maria G. P. M. S. Neves、Artur M. S. Silva、Augusto C. Tomé、Vitor F. Ferreira、José A. S. Cavaleiro

  DOI：10.1071/ch11013

  日期：——

  meso-Tetrakis(pentafluorophenyl)porphyrin reacts with aminoalkylphosphoramidates to afford porphyrins substituted with one or four phosphoramidate groups in the 4-position of the meso-aryl groups. The new porphyrin derivatives show high photostability and some are better singlet oxygen generators than meso-tetrakis(1-methylpyridinium-4-yl)porphyrin, a well known good singlet oxygen producer.

  中-四(五氟苯基)卟啉与氨基烷基磷酰胺发生反应，生成在中-芳基的 4 位上被一个或四个磷酰胺基团取代的卟啉。新的卟啉衍生物具有很高的光稳定性，其中一些比中-四（1-甲基吡啶鎓-4-基）卟啉（一种众所周知的优良单线态氧生成物）具有更好的单线态氧生成能力。
• Selective Monophosphorylation of Aliphatic Diamines
  作者：Marcos Costa de Souza、William Pires de Macedo、Thiago Silva Torres、Leandro Ferreira Pedrosa、Helmut G. Alt

  DOI：10.1080/10426500500543776

  日期：2006.8.1

  This article describes an improved method to synthesize phosphoramidic acid aminoalkyl esters from diamines by the adaptation of industrial patents. Four mono-phosphorylated products having amino sites were obtained in good a yield. Such compounds have potential coordination properties with transition metals and also potential biological activity.
• Synthesis, Crystal Structures, and in Silico Toxicity Prediction of Thienopyridine Phosphoramidates
  作者：Leandro F. Pedrosa、William P. de Macedo、Antonia C. R. Furtado、Guilherme P. Guedes、Luiz C. S. Pinheiro、Jackson A. L. C. Resende、Maria G. F. Vaz、Alice M. R. Bernardino、Marcos C. de Souza

  DOI：10.1080/00397911.2013.786092

  日期：2013.12.17

  New thieno[2,3-b]pyridine phosphoramidates compounds were synthesized and characterized by infrared; H-1, C-13, and P-31 NMR spectroscopy; and high-resolution mass spectrometry. The products were obtained in good yields (64-82%) under mild conditions by nucleophilic aromatic substitution reaction of aminoalkylphosphoramidates over 4-chlorothieno[2,3-b]pyridine-5-carbonitrile. The crystal structures of two compounds were solved by x-ray diffraction and showed a network of intermolecular interactions involving phosphoramidate groups. Druglike properties and toxicity of the new compounds were studied with the help of the software Molinspiration, Osiris, and Toxtree, and were compared with the standard drugs amphotericin B, miltefosine, benznidazole, and nifurtimox. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]
• Synthesis of New Conjugates 1H‑Pyrazolo[3,4-b]pyridine-phosphoramidate and Evaluation against Leishmania amazonensis
  作者：Antonia Medeiros、Julio Borges、Klaus Becker、Raquel Rodrigues、Leonor Leon、Marilene Canto-Cavalheiro、Alice Bernardino、Marcos de Souza、Leandro Pedrosa

  DOI：10.21577/0103-5053.20170126

  日期：——

  In this research three series of substituted 1H-pyrazolo[3,4-b]pyridine phosphoramidates were synthesized and characterized by infrared, H-1, C-13, and P-31 nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry. The products were obtained in good yields (67-83%) under mild conditions by nucleophilic aromatic substitution reaction of aminoalkylphosphoramidates over 4-chloro-1H-pyrazolo[3,4-b]pyridines. These compounds were evaluated as antileishmanials against Leishmania amazonensis promastigotes in vitro. Among all, compounds of a series showed expressive antileishmanial activity. Two of them emerged as the most active, with IC50 values of 6.44 +/- 1.49 and 12.25 +/- 0.68 mu M. The cytotoxicity of this series was assessed on murine cells and presented values similar to the reference drug pentamidine.
• Synthesis and characterization of new 1H-pyrazolo[3,4-b]pyridine phosphoramidate derivatives
  作者：Leandro Ferreira Pedrosa、William Pires de Macedo、Antonia Carlene Rodrigues Furtado、Guilherme Pereira Guedes、Julio Cesar Borges、Jackson Antonio Lamounier Camargos Resende、Maria das Graças Fialho Vaz、Alice Maria Rolim Bernardino、Marcos Costa de Souza

  DOI：10.3998/ark.5550190.p008.413

  日期：——

  Twelve new 1 H-pyrazolo[3,4-b]pyridine phosphoramidate derivatives were synthesized under mild conditions by nucleophilic aromatic substitution reaction of aminoalkylphosphoramidates over 4-Cl substituted pyrazolo[3,4-b]pyridine in good yields. The new compounds were characterized by IR, 1 H, 13 C and 31 P NMR spectroscopy and HRMS. The crystal structure of one compound was solved by X-ray diffraction

  十二个新的 1 H-吡唑并 [3,4-b] 吡啶氨基磷酸酯衍生物在温和条件下通过氨基烷基氨基磷酸酯在 4-Cl 取代的吡唑并 [3,4-b] 吡啶上的亲核芳香取代反应以良好的产率合成。新化合物通过红外、 1 H、 13 C 和 31 P NMR 光谱和 HRMS 进行了表征。一种化合物的晶体结构通过 X 射线衍射解析，并显示出涉及氨基磷酸酯基团的分子间相互作用网络。