diethyl (E)-1-nonenylphosphonate | 81399-32-8

• 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: diethyl (E)-1-nonenylphosphonate
• 英文别名: diethyl 1-nonenylphosphonate；1-diethylphosphono-1-nonene；(E)-1-diethoxyphosphoryl-non-1-ene；(E)-1-diethoxyphosphorylnon-1-ene
• CAS: 81399-32-8
• 化学式: C₁₃H₂₇O₃P
• 分子量: 262.329
• InChiKey: VWXIUBCXENJOHN-OUKQBFOZSA-N

物化性质

• 沸点：
  86-88 °C(Press: 0.03 Torr)
• 密度：
  0.9572 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  diethyl (E)-1-nonenylphosphonate 在 potassium osmate(VI) 甲基磺酰胺 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 作用下， 以 水 、 叔丁醇 为溶剂， 反应 50.0h， 生成 diethyl (1S,2S)-1,2-dihydroxynonylphosphonate 、 diethyl (1R,2R)-1,2-dihydroxynonylphosphonate
  参考文献：
  名称：

  Enantioselective synthesis of threo-α,β-dihydroxyphosphonates by asymmetric dihydroxylation of 1(E)-alkenylphosphonates with AD-mix reagents

  摘要：

  Asymmetric dihydroxylation (AD) of 1(E)-alkenylphosphonates with an AD-mix -alpha or -beta reagent was examined to give a series of optically active threo-alpha,beta-dihydroxyphosphonates. Good enantioselectivity (>88% eel was observed in the AD reaction of 1(E)-alkenylphosphonates with conjugated aromatic substituents. The steric effects of the ester functionality in the course of the dihydroxylation were also evaluated. Enantioselectivity and yield were significantly improved when the AD reaction was carried out with dimethyl phosphonate instead of diethyl phosphonate. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10341-6
• 作为产物：
  描述：

  [1-(Pyridine-2-sulfinyl)-nonyl]-phosphonic acid diethyl ester 以 甲苯 为溶剂， 反应 1.0h， 以65%的产率得到diethyl (E)-1-nonenylphosphonate
  参考文献：
  名称：

  Corsano, Stefano; Mastalia, Assunta; Castagnino, Enzo, Gazzetta Chimica Italiana, 1989, vol. 119, # 11, p. 597 - 600

  摘要：

  DOI：

文献信息

• Copper-Catalyzed Microwave-Expedited Oxyphosphorylation of Alkynes with Diethyl Phosphite and <i>t</i>-Butyl Hydroperoxide Synthesis of Densely Functionalized Phosphonylated Indenones
  作者：Pablo Macías-Benítez、Alfonso Sierra-Padilla、Manuel J. Tenorio、F. Javier Moreno-Dorado、Francisco M. Guerra

  DOI：10.1021/acs.joc.1c01763

  日期：2021.12.3

  Treatment of alkynes with diethyl phosphite and t-butyl hydroperoxide in the presence of [Cu(MeCN)4]BF4 under microwave irradiation produced the oxyphosphorylation of the triple bond, giving rise to the corresponding β-ketophosphonates in moderate-to-good yields. When the triple bond was conjugated to a carbonyl group bearing an aromatic ring, it led to the cyclization of the resulting ketone intermediate

  在微波辐射下，在 [Cu(MeCN) 4 ]BF 4存在下，用亚磷酸二乙酯和叔丁基过氧化氢处理炔烃产生三键的氧磷酸化，从而以中等至良好的产率产生相应的 β-酮膦酸酯. 当三键与带有芳香环的羰基共轭时，会导致生成的酮中间体环化，最终产生不同的膦酰化茚酮。
• Zyablikova, T. A.; Il'yasov, A. V.; Mukhametzyanova, E. Kh., Journal of general chemistry of the USSR, 1982, vol. 52, # 2, p. 249 - 252
  作者：Zyablikova, T. A.、Il'yasov, A. V.、Mukhametzyanova, E. Kh.、Shermergorn, I. M.

  DOI：——

  日期：——
• Rambaud, Monique; Vecchio, Anthony del; Villieras, Jean, Synthetic Communications, 1984, vol. 14, # 9, p. 833 - 842
  作者：Rambaud, Monique、Vecchio, Anthony del、Villieras, Jean

  DOI：——

  日期：——
• CORSANO, STEFANO;MASTALIA, ASSUNTA;CASTAGNINO, ENZO;BARTON, DEREK H. R., GAZZ. CHIM. ITAL., 119,(1989) N1, C. 597-599
  作者：CORSANO, STEFANO、MASTALIA, ASSUNTA、CASTAGNINO, ENZO、BARTON, DEREK H. R.

  DOI：——

  日期：——
• ZYABLIKOVA, T. A.;ILYASOV, A. V.;MUXAMETZYANOVA, EH. X.;SHERMERGORN, I. M+, ZH. OBSHCH. XIMII, 1982, 52, N 2, 287-291
  作者：ZYABLIKOVA, T. A.、ILYASOV, A. V.、MUXAMETZYANOVA, EH. X.、SHERMERGORN, I. M+

  DOI：——

  日期：——