diethyl (3-N,N-diethylaminopropenyl-1,2)phosphonate | 18005-65-7

• 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: diethyl (3-N,N-diethylaminopropenyl-1,2)phosphonate
• 英文别名: 3-Diethylamino-propen-(1)-ylphosphonsaeure-diethylester；3-diethoxyphosphoryl-N,N-diethylprop-2-en-1-amine
• CAS: 18005-65-7
• 化学式: C₁₁H₂₄NO₃P
• 分子量: 249.29
• InChiKey: ZCONMBDBTYBQFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  diethyl (3-N,N-diethylaminopropenyl-1,2)phosphonate 在 sodium hydride 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 15.0h， 生成
  参考文献：
  名称：

  Convenient synthesis of propane aminophosphonic acids, aminodiphosphonic acids and their structural analogues, mediated by azetidinium salts

  摘要：

  The reactions of azetidinium salts with phosphorus nucleophiles R2P(O)H have been investigated. Treatment of O-benzyl-N,N-diethyl-3-hydroxyazetidinium salt 2 with R2P(O)H in the presence of sodium hydride gave the corresponding gamma-N,N-diethylamino-beta-benzyloxypropylphosphonate 6a or phosphine oxide 6b. After debenzylation gamma-N,N-diethylamino-beta-hydroxypropylphosphonate 3a and phosphine oxide 3b were obtained. The compound 6a was converted into its sulfonate ester 8 which underwent elimination to yield 4. The structure 4 has been employed in Michael addition of R2P(O)H to form compounds 5 containing two phosphorus centers. Further compounds of type 3 have been transformed into compounds 5 by reaction with R2P(O)H in the presence of 1.1 equivalents of NaH in boiling toluene. Finally, azetidinium salts 1 have been converted into compounds 5a by reaction with two equivalents of R2P(O)H in the presence of 2.1 equivalents of NaH. Molecular mechanics with implementation of the Allinger MM2 force field and semiempirical AM1 and PM3 methods were used to investigate structures 5d and 5f. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00698-5
• 作为产物：
  描述：

  1,1’-diethyl-3-hydroxyazetidinium chloride 在 palladium on activated charcoal 吡啶 、 氢氧化钾 、 potassium tert-butylate 、 氢气 、 sodium hydride 作用下， 以 甲醇 、 乙二醇二甲醚 、 二甲基亚砜 、 叔丁醇 为溶剂， 反应 74.0h， 生成 diethyl (3-N,N-diethylaminopropenyl-1,2)phosphonate
  参考文献：
  名称：

  Convenient synthesis of propane aminophosphonic acids, aminodiphosphonic acids and their structural analogues, mediated by azetidinium salts

  摘要：

  The reactions of azetidinium salts with phosphorus nucleophiles R2P(O)H have been investigated. Treatment of O-benzyl-N,N-diethyl-3-hydroxyazetidinium salt 2 with R2P(O)H in the presence of sodium hydride gave the corresponding gamma-N,N-diethylamino-beta-benzyloxypropylphosphonate 6a or phosphine oxide 6b. After debenzylation gamma-N,N-diethylamino-beta-hydroxypropylphosphonate 3a and phosphine oxide 3b were obtained. The compound 6a was converted into its sulfonate ester 8 which underwent elimination to yield 4. The structure 4 has been employed in Michael addition of R2P(O)H to form compounds 5 containing two phosphorus centers. Further compounds of type 3 have been transformed into compounds 5 by reaction with R2P(O)H in the presence of 1.1 equivalents of NaH in boiling toluene. Finally, azetidinium salts 1 have been converted into compounds 5a by reaction with two equivalents of R2P(O)H in the presence of 2.1 equivalents of NaH. Molecular mechanics with implementation of the Allinger MM2 force field and semiempirical AM1 and PM3 methods were used to investigate structures 5d and 5f. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00698-5

文献信息

• Umpolung in allylic phosphonates. Regio- and stereo-selective synthesis of (E)-γ-amino-α,β-unsaturated phosphonates by palladium-catalysed reaction of allylic acetoxy phosphonates
  作者：Jingyang Zhu、Xiyan Lu

  DOI：10.1039/c39870001318

  日期：——

  γ-Amino-α,β-unsaturated phosphonates have been synthesized regio- and stereo-selectively in high yield by the reaction of allylic α-acetoxy phosphonates with secondary amines catalysed by palladium.

  γ-氨基-α，β-不饱和膦酸酯是通过烯丙基α-乙酰氧基膦酸酯与钯催化的仲胺反应，以区域和立体选择性高产率合成的。
• Lavielle,G. et al., Bulletin de la Societe Chimique de France, 1967, p. 4186 - 4194
  作者：Lavielle,G. et al.

  DOI：——

  日期：——
• Convenient synthesis of propane aminophosphonic acids, aminodiphosphonic acids and their structural analogues, mediated by azetidinium salts
  作者：A Bakalarz、J Heliński、B Krawiecka、J Michalski、M.J Potrzebowski

  DOI：10.1016/s0040-4020(99)00698-5

  日期：1999.10

  The reactions of azetidinium salts with phosphorus nucleophiles R2P(O)H have been investigated. Treatment of O-benzyl-N,N-diethyl-3-hydroxyazetidinium salt 2 with R2P(O)H in the presence of sodium hydride gave the corresponding gamma-N,N-diethylamino-beta-benzyloxypropylphosphonate 6a or phosphine oxide 6b. After debenzylation gamma-N,N-diethylamino-beta-hydroxypropylphosphonate 3a and phosphine oxide 3b were obtained. The compound 6a was converted into its sulfonate ester 8 which underwent elimination to yield 4. The structure 4 has been employed in Michael addition of R2P(O)H to form compounds 5 containing two phosphorus centers. Further compounds of type 3 have been transformed into compounds 5 by reaction with R2P(O)H in the presence of 1.1 equivalents of NaH in boiling toluene. Finally, azetidinium salts 1 have been converted into compounds 5a by reaction with two equivalents of R2P(O)H in the presence of 2.1 equivalents of NaH. Molecular mechanics with implementation of the Allinger MM2 force field and semiempirical AM1 and PM3 methods were used to investigate structures 5d and 5f. (C) 1999 Elsevier Science Ltd. All rights reserved.