(piperidin-1-ylmethyl)phosphonic acid diethyl ester | 4972-40-1

• 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: (piperidin-1-ylmethyl)phosphonic acid diethyl ester
• 英文别名: piperidin-1-ylmethyl-phosphonic acid diethyl ester；piperidinomethyl-phosphonic acid diethyl ester；Piperidinomethyl-phosphonsaeure-diaethylester；Diethyl piperidin-1-ylmethylphosphonate；1-(diethoxyphosphorylmethyl)piperidine
• CAS: 4972-40-1
• 化学式: C₁₀H₂₂NO₃P
• 分子量: 235.263
• InChiKey: QUZRMJFKXDYSMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (piperidin-1-ylmethyl)phosphonic acid diethyl ester 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  EFFICIENT SYNTHESIS OF α-ENAMINOPHOSPHONATES IN THE SERIES OF PIPERIDINE AND MORPHOLINE. Examples of synthetic applications

  摘要：

  Various alpha-piperidino or alpha-morpholino alkenylphosphonates are conveniently prepared from the related alpha-hetero-substituted methylphosphonates, through a Peterson olefination process, which can be easily adapted for a direct homologation of aldehydes into carboxylic acids. An efficient synthesis of alpha-piperidino or alpha-morpholino alkylphosphonates and phosphonic acids is proposed.

  DOI：

  10.1080/10426509708040491
• 作为产物：
  描述：

  N-甲基哌啶 、 二氯甲烷 、 亚磷酸二乙酯 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以89%的产率得到(piperidin-1-ylmethyl)phosphonic acid diethyl ester
  参考文献：
  名称：

  无催化剂和选择性C–N键功能化：胺，二氯甲烷和负担α-氨基磷化合物的> P（O）H物种的立体三组分偶联

  摘要：

  通过胺，二卤甲烷和> P（O）H物质的三组分偶联，实现了无催化剂和选择性C–N键的官能化。该反应立体定向地进行，并且保留了在磷处的构型，这可以产生各种新的α-氨基酸的旋光性磷类似物。

  DOI：

  10.1021/jo501961h

文献信息

• Synthesen von 2,3-Dioxoalkylphosphonaten und anderer neuartiger ?-Ketophosphonate sowie eines Phosphinopyruvamids ( = (Alkyloxyphosphinyl)pyruvamids)
  作者：Richard Neidlein、Helmut Feistauer

  DOI：10.1002/hlca.19960790329

  日期：1996.5.8

  Syntheses of 2,3-Dioxoalkylphonates and Other Novel β-Ketophosphonates As Well As of a Phosphinopyruvamide ( = (Alkyloxyphosphinyl)pyruvamide)

  2,3-二氧代烷基膦酸酯和其他新型β-酮膦酸酯以及膦酰丙酮酰胺（=（烷氧基膦基）丙酮酰胺）的合成
• Efficient Synthesis of Phosphono‐ and Phosphinoxidomethylated N‐Heterocycles under Solvent‐Free Microwave Conditions
  作者：Ibolya Prauda、István Greiner、Krisztina Ludányi、György Keglevich

  DOI：10.1080/00397910601033856

  日期：2007.2.1

  Abstract Simple N‐heterocycles were converted to N‐phosphono‐ and phosphinoxidomethyl derivatives by a solvent‐free microwave‐assisted condensation of the heterocycle, paraformaldehyde, and diethylphosphite or diphenylphosphine oxide in a convenient and, in most cases, efficient way. In contrast to an earlier report, imidazole proved to be unreactive in this type of phospha‐Mannich reaction.

  摘要 通过杂环、多聚甲醛和二乙基亚磷酸酯或二苯基氧化膦的无溶剂微波辅助缩合，以一种方便且在大多数情况下有效的方式将简单的 N-杂环转化为 N-膦酰基和膦氧化甲基衍生物。与之前的报道相反，咪唑被证明在这种类型的磷-曼尼希反应中没有反应。
• [EN] PYRAZOLOPYRIMIDINONE DERIVATIVES, PROCESS FOR THEIR PREPARATION AND THEIR USE<br/>[FR] DERIVES DE PYRAZOLOPYRIMIDINONE, LEUR PROCEDE DE PREPARATION ET LEUR UTILISATION
  申请人：SK CHEMICALS CO LTD

  公开号：WO2001087888A1

  公开（公告）日：2001-11-22

  This invention relates to a series of pyrazolopyrimidinone derivatives, having an excellent inhibiting activity against cyclic guanosine 3',5'- monophosphate specific phosphodiesterase (cGMP specific PDE; PDE V), process for their preparation, intermediates in their preparation, their uses as therapeutic agents, and pharmaceutical compositions containing them.

  本发明涉及一系列吡唑嘧啶酮衍生物，具有优异的抑制环磷鸟苷3'，5'-单磷酸特异性磷酸二酯酶（cGMP特异性PDE; PDE V）活性，其制备方法、制备中间体、作为治疗剂的用途以及含有它们的药物组合物。
• The Synthesis of Esters of Substituted Amino Phosphonic Acids^1a
  作者：Ellis K. Fields

  DOI：10.1021/ja01126a054

  日期：1952.3
• Synthesis and Acid-Base Properties of  -Aminophosphoryl Compounds
  作者：S. V. Zakharov、G. Kh. Nuriazdanova、A. R. Garifzyanov、V. I. Galkin、R. A. Cherkasov

  DOI：10.1023/b:rugc.0000042422.61124.b3

  日期：2004.6

  alpha-Aminophosphoryl compounds of the phosphonate, phosphine oxide, and alpha,omega-bis(phosphine oxide) series and some of their thiophosphoryl analogs were synthesized. Potentiometric measurements of the pK(a) of the conjugate acids revealed an insignificant effect of variation of substituents on the phosphorus, nitrogen, and alpha-carbon atoms on the basicity of the phosphorylated amines. The latter are weak bases. Organophosphorus groups decrease the basicity of the amines by almost 5 pK(a) units. The role of the hydrophobic effect and intramolecular H-bonding in the obtained substances was discussed.