diethyl α,α-difluoro-4-(2-benzothiazolyl)benzylphosphonate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: diethyl α,α-difluoro-4-(2-benzothiazolyl)benzylphosphonate
• 英文别名: α,α-difluorofostedil；2-[4-[Diethoxyphosphoryl(difluoro)methyl]phenyl]-1,3-benzothiazole
• 化学式: C₁₈H₁₈F₂NO₃PS
• 分子量: 397.382
• InChiKey: GTVYIRHZKGNJCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  76.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  溴氟甲基膦酸二乙酯 、 2-(4-iodophenyl)benzothiazole 在 copper(l) chloride 、 镉 作用下， 生成 diethyl α,α-difluoro-4-(2-benzothiazolyl)benzylphosphonate
  参考文献：
  名称：

  通过CuCl促进（二乙基膦酰基）二氟甲基镉试剂与芳基碘化物的偶联反应，轻松，通用地制备α，α-二氟苄基膦酸酯

  摘要：

  通过（二乙基膦酰基）二氟甲基镉试剂与芳基碘化物的CuCl促进的偶联反应，已经制备了一系列高产率（65-88％）的α，α-二氟苄基膦酸酯。

  DOI：

  10.1016/0040-4039(96)00420-0

文献信息

• A facile and general preparation of α,α-difluoro benzylic phosphonates by the CuCl promoted coupling reaction of the (diethylphosphonyl)difluoromethylcadmium reagent with aryl lodides
  作者：Weiming Qiu、Donald J. Burton

  DOI：10.1016/0040-4039(96)00420-0

  日期：1996.4

  A series of α,α-difluorobenzylic phosphonates have been prepared in good yield (65–88%) by the CuCl promoted coupling reaction of the (diethylphosphonyl)difluoromethylcadmium reagent with aryl iodides.

  通过（二乙基膦酰基）二氟甲基镉试剂与芳基碘化物的CuCl促进的偶联反应，已经制备了一系列高产率（65-88％）的α，α-二氟苄基膦酸酯。
• Nickel‐Catalyzed Cross‐Coupling of Bromodifluoromethylphosphonates with Arylboron Reagents
  作者：Masami Kuriyama、Genki Maeda、Kazuya Kamata、Yusuke Kodama、Kosuke Yamamoto、Osamu Onomura

  DOI：10.1002/adsc.202201140

  日期：2023.1.10

  The nickel-catalyzed cross-coupling of bromodifluoromethylphosphonates with arylboron reagents was developed with a 1,10-phenanthroline-type ligand. In this process, functionalized and heterocycle-containing boroxines were found to be suitable partners, and the catalytic modification of biologically active molecules, such as fenofibrate and indomethacin, was also successfully achieved. Furthermore

  溴二氟甲基膦酸酯与芳基硼试剂的镍催化交叉偶联是用 1,10-菲咯啉型配体开发的。在此过程中，发现功能化和含杂环的环硼氧嘧啶是合适的合作伙伴，并成功实现了非诺贝特和吲哚美辛等生物活性分子的催化修饰。此外，克级反应顺利进行，以高产率得到所需产物。
• Cuprous chloride promoted coupling reaction of diethoxyphosphinyldifluoromethylcadmium reagent with aryl iodides: A practical and convenient preparation of α,α-difluoro benzylic phosphonates
  作者：Weiming Qiu、Donald J. Burton

  DOI：10.1016/j.jfluchem.2013.04.008

  日期：2013.11

  cross coupling reaction of diethoxyphosphinyldifluoromethylcadmium reagent with aryl iodides was promoted by CuCl under mild conditions to give α,α-difluoro benzylic phosphonates in good yields. A variety of functional groups, including halides, phosphonate, nitro, ketone, carboxylic acid and ester in aryl iodides, could be tolerated. This methodology has been successfully applied to prepare α,α-difluoro

  CuCl在温和的条件下促进了二乙氧基次膦基二氟甲基镉试剂与芳基碘的交叉偶联反应，从而以高收率得到了α，α-二氟苄基膦酸酯。可以容许包括芳基碘化物中的卤化物，膦酸酯，硝基，酮，羧酸和酯在内的多种官能团。该方法已经成功地用于制备α，α-二氟Fostedil 9。