(E)-diethyl (3-acetoxy-1-propenyl)phosphonate | 113201-17-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: (E)-diethyl (3-acetoxy-1-propenyl)phosphonate
• 英文别名: (E)-diethyl 3-acetoxyprop-1-enyl phosphonate；[(E)-3-diethoxyphosphorylprop-2-enyl] acetate
• CAS: 113201-17-5
• 化学式: C₉H₁₇O₅P
• 分子量: 236.205
• InChiKey: DMAYTRMOWCTMQX-SOFGYWHQSA-N

物化性质

• 沸点：
  317.0±34.0 °C(Predicted)
• 密度：
  1.119±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 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：

  (E)-diethyl (3-acetoxy-1-propenyl)phosphonate 在 potassium osmate(VI) 吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 AD-mix-α 、 甲基磺酰胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 63.0h， 生成 diethyl (1S,2S)-1,2-dihydroxy-3-(4-methoxybenzoyloxy)propylphosphonate
  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：

  diethyl (E)-1-propenylphosphonate 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 、 丁酮 为溶剂， 反应 16.0h， 生成 (E)-diethyl (3-acetoxy-1-propenyl)phosphonate
  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

文献信息

• Palladium catalysed allylic acetoxylation of dialkyl allyl phosphonates.
  作者：Bruno Principato、Michel Maffei、Chhan Siv、Gérard Buono、Gilbert Peiffer

  DOI：10.1016/0040-4020(95)01046-7

  日期：1996.2

  The catalytic acetoxylation of dialkyl allyl phosphonates with the Pd(OAc)2/benzoquinone/MnO2/HOAc system leads, regioselectively, to dialkyl 3- acetoxy 1-alkenyl phosphonates. On the basis of the regio- and stereoselectivity of the reaction, a mechanism is proposed which involves a (π-allyl) palladium complex as intermediate.

  用Pd（OAc）2 /苯醌/ MnO 2 / HOAc体系催化二烷基烯丙基膦酸酯的乙酰氧基化，选择性地导致3-乙酰氧基1-链烯基膦酸二烷基酯。基于反应的区域选择性和立体选择性，提出了一种机理，该机理涉及（π-烯丙基）钯配合物作为中间体。
• Umpolung in allylic phosphonates. Regioselective reaction of acetoxy allylic phosphonates with nucleophiles catalyzed by palladium(0) complex
  作者：Jingyang Zhu、Xiyan Lu

  DOI：10.1016/s0040-4039(00)96004-0

  日期：1987.1

  Vinylic phosphonates with functional groups can be synthesized regioselectively by the reaction of acetoxy allylic phosphonates with soft carbon nucleophiles in the presence of bis(trimethylsilyl)acetamide (BSA) under palladium(0) catalysis with moderate to good yields.

  在双（三甲基甲硅烷基）乙酰胺（BSA）存在下，在钯（0）催化下，乙酰氧基烯丙基膦酸酯与软碳亲核试剂的反应可区域选择性地合成具有官能团的乙烯基膦酸酯，产率中等至良好。
• 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。
• ZHU, JINGYANG;LU, XIYAN, J. CHEM. SOC. CHEM. COMMUN.,(1987) N 17, 1318-1319
  作者：ZHU, JINGYANG、LU, XIYAN

  DOI：——

  日期：——