[1-(methoxy-methyl-carbamoyl)-ethyl]-phosphonyc acid bis-(2,2,2-trifluoro-ethyl) ester | 448219-33-8

• 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: [1-(methoxy-methyl-carbamoyl)-ethyl]-phosphonyc acid bis-(2,2,2-trifluoro-ethyl) ester
• 英文别名: [1-(methoxy(methyl)carbamoyl)ethyl]phosphonic acid bis(2,2,2-trifluoroethyl) ester；[2-(methoxy(methyl)amino)-1-methyl-2-oxoethyl]phosphonic acid bis(2,2,2-trifluoroethyl) ester；2-[bis(2,2,2-trifluoroethoxy)phosphoryl]-N-methoxy-N-methylpropanamide
• CAS: 448219-33-8
• 化学式: C₉H₁₄F₆NO₅P
• 分子量: 361.178
• InChiKey: LMDUDVXYKXCMMY-UHFFFAOYSA-N

物化性质

• 沸点：
  289.2±50.0 °C(Predicted)
• 密度：
  1.400±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  正辛醛 、 [1-(methoxy-methyl-carbamoyl)-ethyl]-phosphonyc acid bis-(2,2,2-trifluoro-ethyl) ester 在 18-冠醚-6 、 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.83h， 以83%的产率得到Z-methyl-dec-2-enoic acid methoxy-methyl-amide
  参考文献：
  名称：

  A New Bis(2,2,2-trifluoroethyl)phosphonate for the Synthesis of Z-Unsaturated N-Methoxy-N-methylamides

  摘要：

  The N-methoxy-N-methyl bis(2,2,2-trifluoroethyl)phosphonamide was easily obtained via the Arbuzov reaction with use of commercially available tris(2,2,2-trifluoroethyl)phosphite, 2-bromo-N-methoxy-N-methylacetamide, and KF/alumina. The reaction of bis(2,2,2-trifluoroethyl)phosphonate with several aldehydes demonstrates the versatility of the method, which gives Z-unsaturated amides in good yields.

  DOI：

  10.1021/jo025816s
• 作为产物：
  描述：

  二-三氟乙基乙基膦酸酯 、 N-甲氧基-N-甲基氨基甲酰氯 在 正丁基锂 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 以88%的产率得到[1-(methoxy-methyl-carbamoyl)-ethyl]-phosphonyc acid bis-(2,2,2-trifluoro-ethyl) ester
  参考文献：
  名称：

  PREPARATION OF [1-(METHOXYMETHYLCARBAMOYL)ETHYL] PHOSPHONIC ACID BIS-(2,2,2-TRIFLUOROETHYL) ESTER: A USEFUL INTERMEDIATE IN THE SYNTHESIS OF Z-UNSATURATED N-METHOXY-N-METHYLAMIDES

  摘要：

  DOI：

  10.15227/orgsyn.082.0147

文献信息

• Total Synthesis of (±)-Merrilactone A
  作者：Wei He、Jie Huang、Xiufeng Sun、Alison J. Frontier

  DOI：10.1021/ja0761986

  日期：2008.1.1

  The total synthesis of racemic merrilactone A (a neurotrophic agent) is described, featuring simultaneous and stereospecific creation of the C4 and C5 stereocenters via a notable silyloxyfuran Nazarov cyclization. Full details of the successful synthetic strategy are given, as well as several examples of the interesting reactivity of intermediates that were prepared and studied during the execution

  描述了外消旋 merrilactone A（一种神经营养剂）的全合成，其特点是通过显着的甲硅烷氧基呋喃 Nazarov 环化同时和立体定向地创建 C4 和 C5 立体中心。给出了成功合成策略的完整细节，以及在执行全合成过程中制备和研究的中间体的有趣反应性的几个例子。对路易斯酸催化的甲硅烷氧基呋喃 Nazarov 环化进行了详细研究，包括对底物范围和局限性的系统研究。此外，进行的实验表明路易斯酸性硅物质参与了纳扎罗夫环化。
• A New Bis(2,2,2-trifluoroethyl)phosphonate for the Synthesis of <i>Z</i>-Unsaturated <i>N</i>-Methoxy-<i>N</i>-methylamides
  作者：Samuel Fortin、Félix Dupont、Pierre Deslongchamps

  DOI：10.1021/jo025816s

  日期：2002.7.1

  The N-methoxy-N-methyl bis(2,2,2-trifluoroethyl)phosphonamide was easily obtained via the Arbuzov reaction with use of commercially available tris(2,2,2-trifluoroethyl)phosphite, 2-bromo-N-methoxy-N-methylacetamide, and KF/alumina. The reaction of bis(2,2,2-trifluoroethyl)phosphonate with several aldehydes demonstrates the versatility of the method, which gives Z-unsaturated amides in good yields.
• PREPARATION OF [1-(METHOXYMETHYLCARBAMOYL)ETHYL] PHOSPHONIC ACID BIS-(2,2,2-TRIFLUOROETHYL) ESTER: A USEFUL INTERMEDIATE IN THE SYNTHESIS OF Z-UNSATURATED N-METHOXY-N-METHYLAMIDES
  作者：Smith, Amos B.、Beiger, Jason J.、Davulcu, Akin H.、Cox, Jason M.、Lautens, Mark、Taillier, Catherine

  DOI：10.15227/orgsyn.082.0147

  日期：——