diethyl 1-acetyloxy-3-phenyl-2(E)-propenylphosphonate | 202004-44-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: diethyl 1-acetyloxy-3-phenyl-2(E)-propenylphosphonate
• 英文别名: (E)-1-(diethoxyphosphoryl)-3-phenylallyl acetate；[(E)-1-diethoxyphosphoryl-3-phenylprop-2-enyl] acetate
• CAS: 202004-44-2
• 化学式: C₁₅H₂₁O₅P
• 分子量: 312.303
• InChiKey: RTMVVIBSKOSBIX-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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-acetyloxy-3-phenyl-2(E)-propenylphosphonate 在 potassium osmate(VI) AD-mix-α 、 甲基磺酰胺 、 AD-mix-β 作用下， 以 水 、 叔丁醇 为溶剂， 反应 48.0h， 生成 Acetic acid (1R,2S,3R)-1-(diethoxy-phosphoryl)-2,3-dihydroxy-3-phenyl-propyl ester
  参考文献：
  名称：

  Asymmetric dihydroxylation of 1-acyloxy-2(E)-alkenylphosphonates with AD-mix reagents. Effects of 1-acyloxy functional groups on the asymmetric dihydroxylation

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(97)10342-8
• 作为产物：
  描述：

  反式肉桂醛 、 alkaline earth salt of/the/ methylsulfuric acid 在 吡啶 、 titanium(IV) isopropylate 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 15.0h， 生成 diethyl 1-acetyloxy-3-phenyl-2(E)-propenylphosphonate
  参考文献：
  名称：

  Asymmetric dihydroxylation of 1-acyloxy-2(E)-alkenylphosphonates with AD-mix reagents. Effects of 1-acyloxy functional groups on the asymmetric dihydroxylation

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(97)10342-8

文献信息

• Selective Tsuji–Trost type C-allylation of hydrazones: a straightforward entry into 4,5-dihydropyrazoles
  作者：El Hachemia El Mamouni、Martin Cattoen、Marie Cordier、Janine Cossy、Stellios Arseniyadis、Hocine Ilitki、Laurent El Kaïm

  DOI：10.1039/c6cc08171a

  日期：——

  Tsuji–Trost typeC-allylation access to 4,5-dihydropyrazoles.

  辻-トロスト型C-烯丙基化による4,5-二氢ピラ唑の合成方法。
• Facile and High-Yielding Preparation of α-Acetoxyphosphonates from α-Hydroxyphosphonates Assisted by Microwave Irradiation
  作者：Habib Firouzabadi、Nasser Iranpoor、Sara Sobhani、Zohreh Amoozgar

  DOI：10.1055/s-2004-829124

  日期：——

  A convenient and eco-friendly procedure is described for the efficient preparation of a variety of α-acetyloxyphosphonates from their corresponding α-hydroxyphosphonates using acetic anhydride under microwave irradiation in the absence of solvent.

  在无溶剂的条件下，利用醋酸酐在微波辐照下高效地从相应的δ-羟基膦酸盐制备了多种δ-乙酰氧基膦酸盐，该方法既方便又环保。
• OKAMOTO, YOSHIKI;AZUHATA, TOSHIO, BULL. CHEM. SOC. JAP., 1984, 57, N 9, 2693-2694
  作者：OKAMOTO, YOSHIKI、AZUHATA, TOSHIO

  DOI：——

  日期：——
• 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.