Diethyl 1-acetoxyallylphosphonate | 13103-44-1

• 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: Diethyl 1-acetoxyallylphosphonate
• 英文别名: diethyl α-acetoxyallylphosphonate；diethyl 1-acetyloxy-2-propenylphosphonate；Diethyl-(1-acetoxyallyl)-phosphonat；1-(Diethoxyphosphoryl)prop-2-en-1-yl acetate；1-diethoxyphosphorylprop-2-enyl acetate
• CAS: 13103-44-1
• 化学式: C₉H₁₇O₅P
• 分子量: 236.205
• InChiKey: PDZIEAJYXBGHLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Diethyl 1-acetoxyallylphosphonate 在 四(三苯基膦)钯 三乙胺 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以100%的产率得到(E)-diethyl (3-acetoxy-1-propenyl)phosphonate
  参考文献：
  名称：

  烯丙基膦酸酯中的Umpolung。钯催化烯丙基乙酰氧基膦酸酯的区域和立体选择性合成（E）-γ-氨基-α，β-不饱和膦酸酯

  摘要：

  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。

  DOI：

  10.1039/c39870001318
• 作为产物：
  描述：

  磷酸烯丙基二乙酯 、 乙酰氯 生成 Diethyl 1-acetoxyallylphosphonate
  参考文献：
  名称：

  Sturtz,G.; Corbel,B., Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1973, vol. 277, p. 395 - 398

  摘要：

  DOI：

文献信息

• Regio- and Stereoselective Synthesis of Symmetrical and Unsymmetrical 1,3-Diphosphoryl(Phosphonyl, Phosphinyl) Substituted (<i>E</i>)-Propenes
  作者：Xiyan Lu、Xiaochun Tao、Jingyang Zhu、Xiaowei Sun、Jingyan Xu

  DOI：10.1055/s-1989-27407

  日期：——

  Symmetrical and unsymmetrical 1,3-diphosphoryl substituted (E)-propenes were synthesized by the reaction of 1-acetoxyallyl substituted phosphorus compounds (phosphonates, phosphinates, and phosphine oxides) with O,O-dialkyl phosphonates (O-alkyl phosphinates, or dialkyl phosphine oxides) and bis(trimethylsilyl)acetamide (BSA) in the presence of nickel(II) chloride as catalyst, or with trivalent phosphorus acid esters (phosphites, phosphonites, and phosphinites) using only nickel(II) chloride as the catalyst.

  合称对称和非对称的1,3-二磷酸基取代（E)-烯丙烯，是通过1-乙酰氧基烯丙基取代的磷化合物（磷酸酯、磷酸亚酯和磷烯氧化物）与O,O-二烷基磷酸酯（O-烷基磷酸亚酯或二烷基磷烯氧化物）以及双（三甲基硅基）乙酰胺（BSA）在氯化镍（II）作为催化剂的存在下反应合成的，或者与三价磷酸酯（磷酸酯、磷酸亚酯和磷酸亚磷酯）仅使用氯化镍（II）作为催化剂反应。
• Hydroboration of Unsaturated Phosphonic Esters:  Synthesis of Boronophosphonates and Trisubstituted Vinylphosphonates
  作者：Inna Pergament、Morris Srebnik

  DOI：10.1021/ol006836o

  日期：2001.1.1

  [figure: see text] Hydroboration of vinyl phosphonates with pinacolborane (PBH) proceeds to give phosphonoboronates, 2. Surprisingly, such compounds have not been reported before. The reaction works well with terminal alkenylphosphonates. Internal alkenylphosphonates give complex mixtures. Hydroboration/Suzuki coupling of alkynylphosphonates, with PBH, in a one-pot procedure gives trisubstituted vinylphosphonates

  [图：见正文]用频哪醇硼烷（PBH）对膦酸乙烯基酯进行氢硼化可得到膦酰基硼酸酯2。令人惊讶的是，此类化合物以前尚未见报道。该反应与末端烯基膦酸酯一起很好地进行。内部链烯基膦酸酯产生复杂的混合物。单锅法将炔基膦酸酯与PBH进行硼氢化/铃木偶联，可得到具有良好总收率的三取代乙烯基膦酸酯，并提供了这些化合物的新合成方法。
• Asymmetric dihydroxylation of 1-acyloxy-2(E)-alkenylphosphonates with AD-mix reagents. Effects of 1-acyloxy functional groups on the asymmetric dihydroxylation
  作者：Tsutomu Yokomatsu、Takehiro Yamagishi、Tomoyuki Sada、Kenji Suemune、Shiroshi Shibuya

  DOI：10.1016/s0040-4020(97)10342-8

  日期：1998.1

  Asymmetric dihydroxylation (AD) of a racemic mixture of 1-acyloxy-2(E)-alkenylphosphonates with AD-mix-alpha or -beta reagents was examined. The kinetic rate of dihydroxylation was highly dependent upon the configuration of the 1-acyloxy functional group as well as the nature of substituents at the 3-position. ?he reaction of a racemic mixture of diethyl (E)-3-phenyl-1-acetyloxy-2-propenylphosphonate with an AD-mix-beta reagent preferentially dihydroxylated the R-enantiomer to leave an unreacted S-enantiomer of high enantiomeric purity. Double diastereoselection of the resolved diethyl 3-phenyl-1-acetyloxy-2(E)-propenylphosphonate in dihydroxylation was also examined. (C) 1997 Elsevier Science Ltd. All rights reserved.
• An Efficient Route to Chiral α- and β-Hydroxyalkanephosphonates
  作者：Oscar Pàmies、Jan-E. Bäckvall

  DOI：10.1021/jo026888m

  日期：2003.6.1

  Enzymatic kinetic resolution of alpha- and beta-hydroxyphosphonates in combination with ruthenium-catalyzed alcohol isomerization led to a successful dynamic kinetic resolution. A variety of racemic hydroxyphosphonates were efficiently transformed to the corresponding enantiomerically pure acetates (ee up to 99% and yield up to 87%).
• Pudovik,A.N. et al., Journal of general chemistry of the USSR, 1973, vol. 43, p. 1896 - 1900
  作者：Pudovik,A.N. et al.

  DOI：——

  日期：——