3-(methylamino)propylphosphonic acid | 72696-93-6

• 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: 3-(methylamino)propylphosphonic acid
• 英文别名: Hydroxy-[3-(methylazaniumyl)propyl]phosphinate
• CAS: 72696-93-6
• 化学式: C₄H₁₂NO₃P
• 分子量: 153.118
• InChiKey: DRXLIERDDOQKTL-UHFFFAOYSA-N

物化性质

• 熔点：
  240 °C
• 沸点：
  325.4±44.0 °C(Predicted)
• 密度：
  1.249±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  77
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(methylamino)propylphosphonic acid 、 甲乙酐 反应 12.0h， 以15%的产率得到[3-(Formyl-methyl-amino)-propyl]-phosphonic acid
  参考文献：
  名称：

  Evaluation of fosmidomycin analogs as inhibitors of the Synechocystis sp. PCC6803 1-deoxy-d-xylulose 5-phosphate reductoisomerase

  摘要：

  Analogs of the antibiotic fosmidomycin, an inhibitor of the methylerythritol phosphate pathway to isoprenoids, were synthesized and evaluated against the recombinant Synechocystis sp. PCC6803 1-deoxy-D-xylulose 5-phosphate reductoisomerase (DXR). Fosfoxacin, the phosphate analog of fosmidomycin, and its acetyl congener were found to be more potent inhibitors of DXR than fosmidomycin. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.11.012
• 作为产物：
  描述：

  {3-[(Diethoxy-phosphoryl)-methyl-amino]-propyl}-phosphonic acid diethyl ester 在 盐酸 作用下， 生成 3-(methylamino)propylphosphonic acid
  参考文献：
  名称：

  制备d'酸氨基烷基膦酸酰胺'd'ω-卤代烷基胺磷酸基。

  摘要：

  氨基烷基膦酸是通过氮-磷（PN）键形成的氨基保护基来制备的。β或γ-溴代烷基胺用氯磷酸盐进行磷酸化，然后使所得卤代烷基膦酰胺化物与亚磷酸三乙酯反应（Arbuzov反应），得到可以用各种试剂烷基化的氨基磷酸酯-膦酸酯中间体。可以通过用氯化氢水溶液处理来除去磷酰基残基。描述了对氨基膦酸的分离的改进。

  DOI：

  10.1016/0040-4020(79)85028-0

文献信息

• Collignon, N.; Fabre, G.; Varlet, J. M., Phosphorus and Sulfur and the Related Elements, 1981, vol. 10, p. 81 - 86
  作者：Collignon, N.、Fabre, G.、Varlet, J. M.、Savignac, Ph.

  DOI：——

  日期：——
• Modifications around the hydroxamic acid chelating group of fosmidomycin, an inhibitor of the metalloenzyme 1-deoxyxylulose 5-phosphate reductoisomerase (DXR)
  作者：Catherine Zinglé、Lionel Kuntz、Denis Tritsch、Catherine Grosdemange-Billiard、Michel Rohmer

  DOI：10.1016/j.bmcl.2012.09.021

  日期：2012.11

  Fosmidomycin derivatives in which the hydroxamic acid group has been replaced by several bidentate chelators as potential hydroxamic alternatives were prepared and tested against the DXR from Escherichia coli. These results illustrate the predominant role of the hydroxamate functional group as the most effective metal binding group in DXR inhibitors. (C) 2012 Elsevier Ltd. All rights reserved.
• BRIGOT D.; COLLIGNON N.; SAVIGNAC PH., TETRAHEDRON, 1979, 35, NO 11, 1345-1355
  作者：BRIGOT D.、 COLLIGNON N.、 SAVIGNAC PH.

  DOI：——

  日期：——
• COLLIGNON N.; FABRE G.; VARLET J. M.; SAVIGNAC P., PHOSPH. AND SULFUR, 1981, 10, NO 1, 81-86
  作者：COLLIGNON N.、 FABRE G.、 VARLET J. M.、 SAVIGNAC P.

  DOI：——

  日期：——
• Evaluation of fosmidomycin analogs as inhibitors of the Synechocystis sp. PCC6803 1-deoxy-d-xylulose 5-phosphate reductoisomerase
  作者：Youn-Hi Woo、Roberta P.M. Fernandes、Philip J. Proteau

  DOI：10.1016/j.bmc.2005.11.012

  日期：2006.4

  Analogs of the antibiotic fosmidomycin, an inhibitor of the methylerythritol phosphate pathway to isoprenoids, were synthesized and evaluated against the recombinant Synechocystis sp. PCC6803 1-deoxy-D-xylulose 5-phosphate reductoisomerase (DXR). Fosfoxacin, the phosphate analog of fosmidomycin, and its acetyl congener were found to be more potent inhibitors of DXR than fosmidomycin. (c) 2005 Elsevier Ltd. All rights reserved.