(4-Chloro-2-diethoxyphosphorylphenyl) 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate | 1227161-30-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: (4-Chloro-2-diethoxyphosphorylphenyl) 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate
• CAS: 1227161-30-9
• 化学式: C₁₄H₁₃ClF₉O₆PS
• 分子量: 546.732
• InChiKey: OBZIANNPVOLRJD-UHFFFAOYSA-N

物化性质

• 沸点：
  440.3±45.0 °C(Predicted)
• 密度：
  1.59±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  87.3
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  (4-Chloro-2-diethoxyphosphorylphenyl) 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate 、 丙烯酸甲酯（MA） 在 bis-triphenylphosphine-palladium(II) chloride 、 三乙胺 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以80%的产率得到(E)-3-[4-chloro-2-(diethoxyphosphoryl)phenyl]acrylic acid methyl ester
  参考文献：
  名称：

  钯（0）/碘盐介导的芳基非aflates的Heck反应：在2-（1-烯基）苯基膦酸酯的合成中的应用

  摘要：

  发现碘化物盐，例如NaI，KI或n- Bu 4 NI（TBAI），而不是溴化物或氯化物盐，在Pd（0）催化的芳基壬二酸酯和末端烯烃的Heck反应中起关键作用。在DMF中存在PdCl 2（PPh 3）2，NaI或TBAI时，首先通过邻位反应生成一类2-（1-烯基）苯基膦酸酯-膦酰基苯基壬酸酯与烯烃的产率，区域选择性和立体选择性在很大程度上取决于取代基的性质。在芳基壬酸酯不与烯烃带有空间位阻膦酰基的情况下，反应在相同条件下进行得更平稳，从而以良好或极好的收率选择性地产生线性产物。讨论了这种反应的原理。

  DOI：

  10.1016/j.jfluchem.2011.06.029
• 作为产物：
  描述：

  全氟丁基磺酰氟 、 5-氯-2-羟基苯基膦酸二乙酯 在 三乙胺 作用下， 生成 (4-Chloro-2-diethoxyphosphorylphenyl) 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate
  参考文献：
  名称：

  Phosphaisocoumarins as a new class of potent inhibitors for pancreatic cholesterol esterase

  摘要：

  Due to the importance of pancreatic cholesterol esterase (CEase) as a potential target in atherosclerosis and for the development of hypocholesterolemic agents, there are increasing interests in designing and synthesizing CEase inhibitors. In the present study, we prepared forty-five isocoumarin phosphorus analogues (i.e., phosphaisocoumarins) and investigated the inhibition of these compounds on the CEase. The results showed that some phosphaisocoumarins could act as potent inhibitors of CEase. The most potent inhibitors, compounds 9d, 10a and 12e give IC(50) values of 4.8 mu M, 2.3 mu M and 1.9 mu M, respectively. The inhibition mechanism and kinetic characterization studies indicate that they are reversible competitive inhibitors. (C) 2010 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2010.01.038

文献信息

• An efficient synthesis of 2-(1-(E)-alkenyl)phenylphosphonates via Suzuki reaction of aryl nonaflates with (E)-1-alkenylboronates
  作者：Ai-Yun Peng、Ba-Tian Chen、Pei-Jiang Chen

  DOI：10.1016/j.jfluchem.2013.03.015

  日期：2013.7

  Suzuki coupling reaction between 2-phosphonylaryl nonaflates and (E)-1-alkenylboronic pinacol esters using Pd(OAc)2/PPh3 as catalysts, K2CO3 as base and DMF as solvent has been developed. This strategy allows for convenient synthesis of twelve 2-(1-(E)-alkenyl)phenylphosphonates in good to excellent yields, most of which are not readily available by the previously reported Heck reaction of the same aryl

  2- phosphonylaryl全氟丁磺酸根和（之间的有效和通用的Suzuki偶合反应ë）-1- alkenylboronic频哪醇酯使用Pd（OAc）2 / PPH 3作为催化剂，K 2 CO 3作为碱和DMF作为溶剂已经研制成功。这种策略允许的12 2-（1-（方便合成Ë到优异的产率，其中大部分是不容易获得由相同的芳基全氟丁磺酸根和末端烯烃的先前报道的Heck反应在良好） -烯基）phenylphosphonates。
• Pd(0)/iodide salt-mediated Heck reaction of aryl nonaflates: Application to the synthesis of 2-(1-alkenyl)phenylphosphonates
  作者：Ai-Yun Peng、Ba-Tian Chen、Zheng Wang、Bo Wang、Xiao-Bin Mo、Yuan-You Wang、Pei-Jiang Chen

  DOI：10.1016/j.jfluchem.2011.06.029

  日期：2011.11

  chloride salt, was found to play a key role in the Pd(0)-catalyzed Heck reaction of aryl nonaflates and terminal alkenes. In the presence of PdCl2(PPh3)2, NaI or TBAI in DMF, a class of 2-(1-alkenyl)phenylphosphonates was first synthesized via the reaction of o-phosphonylphenyl nonaflates with alkenes, the yields, regioselectivities and stereoselectivities were much dependent on the nature of the substituents

  发现碘化物盐，例如NaI，KI或n- Bu 4 NI（TBAI），而不是溴化物或氯化物盐，在Pd（0）催化的芳基壬二酸酯和末端烯烃的Heck反应中起关键作用。在DMF中存在PdCl 2（PPh 3）2，NaI或TBAI时，首先通过邻位反应生成一类2-（1-烯基）苯基膦酸酯-膦酰基苯基壬酸酯与烯烃的产率，区域选择性和立体选择性在很大程度上取决于取代基的性质。在芳基壬酸酯不与烯烃带有空间位阻膦酰基的情况下，反应在相同条件下进行得更平稳，从而以良好或极好的收率选择性地产生线性产物。讨论了这种反应的原理。
• Phosphaisocoumarins as a new class of potent inhibitors for pancreatic cholesterol esterase
  作者：Baojian Li、Binhua Zhou、Hailiang Lu、Lin Ma、Ai-Yun Peng

  DOI：10.1016/j.ejmech.2010.01.038

  日期：2010.5

  Due to the importance of pancreatic cholesterol esterase (CEase) as a potential target in atherosclerosis and for the development of hypocholesterolemic agents, there are increasing interests in designing and synthesizing CEase inhibitors. In the present study, we prepared forty-five isocoumarin phosphorus analogues (i.e., phosphaisocoumarins) and investigated the inhibition of these compounds on the CEase. The results showed that some phosphaisocoumarins could act as potent inhibitors of CEase. The most potent inhibitors, compounds 9d, 10a and 12e give IC(50) values of 4.8 mu M, 2.3 mu M and 1.9 mu M, respectively. The inhibition mechanism and kinetic characterization studies indicate that they are reversible competitive inhibitors. (C) 2010 Published by Elsevier Masson SAS.