diethyl aziridin-1-ylphosphonate | 470-27-9

• 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: diethyl aziridin-1-ylphosphonate
• 英文别名: N-(diethoxyphosphinoyl)aziridine；N-(diethoxyphosphoryl)aziridine；aziridin-1-yl-phosphonic acid diethyl ester；Aziridin-1-yl-phosphonsaeure-diaethylester；1-Diethoxyphosphorylaziridine
• CAS: 470-27-9
• 化学式: C₆H₁₄NO₃P
• 分子量: 179.156
• InChiKey: OUIORVSEVVCFSN-UHFFFAOYSA-N

物化性质

• 沸点：
  60-61 °C(Press: 0.03 Torr)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl aziridin-1-ylphosphonate 以 乙醚 为溶剂， 生成
  参考文献：
  名称：

  Gubnitskaya,E.S. et al., Journal of general chemistry of the USSR, 1973, vol. 43, p. 737 - 740

  摘要：

  DOI：
• 作为产物：
  描述：

  diethyl N-(2-chloroethyl)phosphoramidate 在 sodium hydroxide 、 四丁基硫酸氢铵 、 potassium carbonate 作用下， 以 苯 为溶剂， 反应 4.0h， 生成 diethyl aziridin-1-ylphosphonate
  参考文献：
  名称：

  Two-Carbon Homologation of Grignard Reagents to Primary Amines

  摘要：

  描述了一种新颖、便捷的N-(二乙氧基磷酰基)叠氮烷合成方法。展示了这种化合物作为氨基乙基化的合成等效物在格氏试剂中的应用。

  DOI：

  10.1055/s-1996-4213

文献信息

• Novel Organophosphorus Reagents for the Synthesis of Amines
  作者：Andrzej Zwierzak、Krystyna Osowska-Pacewicka

  DOI：10.1080/10426509608545217

  日期：1996.1

  Abstract: New organophosphorus equivalents of a2 type N-protected amine synthons are presented.

  摘要：介绍了 a2 型 N 保护胺合成子的新有机磷等价物。
• Synthesis of Chiral Amphetamine Derivatives by Stereospecific, Regioselective Cuprate Addition Reaction with Aziridine Phosphoramidate Compounds
  申请人：Yang Je

  公开号：US20150183716A1

  公开（公告）日：2015-07-02

  The invention includes processes for the synthesis of amphetamine, dexamphetamine, methamphetamine, derivatives of these, including their salts, and novel precursors and intermediates obtained thereby, by synthesizing aziridine phosphoramidate compounds in specified solvents at specified temperatures, and then converting to a novel aryl or aryl-alkyl phosphoramidate precursors using an organometallic compound such as a copper salt, where the novel aryl or aryl-alkyl phosphoramidate precursor is then easily converted to the target compounds using known reactions,

  这项发明包括合成安非他命、右旋安非他命、甲基苯丙胺及其衍生物（包括盐）的过程，以及通过在指定溶剂中在指定温度下合成环氮磷酰胺化合物，然后利用有机金属化合物（如铜盐）将其转化为新型芳基或芳基烷基磷酰胺前体，然后利用已知反应将新型芳基或芳基烷基磷酰胺前体轻松转化为目标化合物。
• α,β-Aziridinylphosphonates by lithium amide-induced phosphonyl migration from nitrogen to carbon in terminal aziridines
  作者：David M Hodgson、Zhaoqing Xu

  DOI：10.3762/bjoc.6.110

  日期：——

  N-Phosphonate terminal aziridines undergo lithium 2,2,6,6-tetramethylpiperidide-induced N- to C-[1,2]-anionic phosphonyl group migration under experimentally straightforward conditions, to provide a stereocontrolled access to synthetically valuable trans-alpha,beta-aziridinylphosphonates. The utility of this chemistry has been demonstrated in the asymmetric synthesis of a beta-aminophosphonate.

  N-膦酸酯末端氮丙啶在实验简单的条件下经历 2,2,6,6-四甲基哌啶锂诱导的 N-到 C-[1,2]-阴离子膦酰基迁移，以提供对合成有价值的反式-α 的立体控制访问， β-氮丙啶膦酸盐。这种化学方法的效用已在 β-氨基膦酸酯的不对称合成中得到证明。
• Synthesis and functionalization of organophosphorus-substituted amines with PCH2NH fragments
  作者：Andrey A. Prishchenko、Mikhail V. Livantsov、Olga P. Novikova、Ludmila I. Livantsova、Valery S. Petrosyan

  DOI：10.1002/hc.20602

  日期：——

  The convenient procedures for the synthesis of new organophosphorus-substituted amines with the PCH2NH moiety are proposed, starting from the derivatives of organophosphorus PH-acids, as well as 1,3,5-trisubstituted hexahydro-1,3,5-triazines as aminomethylating reagents. Various reactions of functionalization (such as acylation, carboxyethylation, pyridylethylation, and aminoethylation) of the obtained

  从有机磷 PH 酸的衍生物以及 1,3,5-三取代的六氢-1,3,5-三嗪作为氨甲基化开始，提出了合成具有 PCH2NH 部分的新型有机磷取代胺的简便方法试剂。介绍了所得有机磷取代胺的各种官能化反应（如酰化、羧乙基化、吡啶乙基化和氨乙基化）。© 2010 Wiley Periodicals, Inc. 杂原子化学 21:236–241, 2010; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20602
• Reactions of N-Phosphorylated Aziridines with Dianions Derived from Ethyl Acetoacetate and 1,3-Diketones: New Route to Substituted Pyrrolines and Pyrrolidines
  作者：Krystyna Osowska-Pacewicka、Andrzej Zwierzak

  DOI：10.1080/00397919808005953

  日期：1998.4

  Abstract The nucleophilic ring-opening of N-(diethoxyphosphory)aziridines by the dianions derived from ethyl acetoacetate and 1,3-diketones has been studied. Acid-mediated cyclisation and dephosphorylation of the resulting products to a number of substituted pyrrolines and pyrrolidines has been also investigated.

  摘要 研究了乙酰乙酸乙酯和 1,3-二酮衍生的二价阴离子对 N-（二乙氧基磷酸）氮丙啶的亲核开环。还研究了酸介导的环化和去磷酸化生成的许多取代吡咯啉和吡咯烷的产物。