[Difluoro-(4-iodo-phenyl)-methyl]-phosphonic acid diethyl ester | 156017-41-3

• 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: [Difluoro-(4-iodo-phenyl)-methyl]-phosphonic acid diethyl ester
• 英文别名: diethyl α,α-difluoro-4-iodobenzylphosphonate；Diethyl (4-iodophenyl)difluoromethylphosphonate；diethyl 4-iodo-phosphono(difluoromethyl)benzene；diethyl difluoro(4-iodophenyl)methylphosphonate；1-[diethoxyphosphoryl(difluoro)methyl]-4-iodobenzene
• CAS: 156017-41-3
• 化学式: C₁₁H₁₄F₂IO₃P
• 分子量: 390.105
• InChiKey: ZUVRQZGOJFKMIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [Difluoro-(4-iodo-phenyl)-methyl]-phosphonic acid diethyl ester 在 bis-triphenylphosphine-palladium(II) chloride 、 lithium hydroxide 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 6.33h， 生成 (2S)-2-[(tert-butoxycarbonyl)amino]-3-{4-[(diethoxyphosphoryl)(difluoro)methyl]phenyl}propanoic acid
  参考文献：
  名称：

  ENANTIOSELECTIVE SYNTHESIS OF N-Boc AND N-Fmoc PROTECTED DIETHYL 4-PHOSPHONO(DIFLUOROMETHYL)-L-PHENYLALANINE (F₂Pmp)

  摘要：

  DOI：

  10.1080/00304949609355909
• 作为产物：
  描述：

  二乙基(4-碘苯甲酰基)膦酸酯 在 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以64%的产率得到[Difluoro-(4-iodo-phenyl)-methyl]-phosphonic acid diethyl ester
  参考文献：
  名称：

  ENANTIOSELECTIVE SYNTHESIS OF N-Boc AND N-Fmoc PROTECTED DIETHYL 4-PHOSPHONO(DIFLUOROMETHYL)-L-PHENYLALANINE (F₂Pmp)

  摘要：

  DOI：

  10.1080/00304949609355909

文献信息

• Phosphonic acid derivatives as inhibitors of protein tyrosine phosphatase IB (PTP-IB)
  申请人：——

  公开号：US20020052344A1

  公开（公告）日：2002-05-02

  The invention encompasses the novel class of compounds represented by formula I which are inhibitors of the PTP-1B enzyme. 1 The invention also encompasses pharmaceutical compositions and methods of treating or preventing PTP-1B mediated diseases, including diabetes, obesity, and diabetes-related diseases.

  本发明包括一类新颖的化合物，这些化合物由公式I表示，是PTP-1B酶的抑制剂。 本发明还包括用于治疗或预防PTP-1B介导的疾病的药物组合物和方法，包括糖尿病、肥胖症和与糖尿病相关的疾病。
• Compounds, compositions and methods for inhibiting the binding of
  申请人：Warner-Lambert Company

  公开号：US05922697A1

  公开（公告）日：1999-07-13

  The present invention provides compounds that inhibit the binding of proteins containing an SH2 domain to cognate phosphorylated proteins. The invention also provides pharmaceutical compositions containing the compounds and methods of inhibiting the binding of proteins containing an SH2 domain to cognate phosphorylated proteins.

  本发明提供了抑制含有SH2结构域蛋白与同源磷酸化蛋白结合的化合物。该发明还提供了含有这些化合物的药物组合物以及抑制含有SH2结构域蛋白与同源磷酸化蛋白结合的方法。
• Facile syntheses of building blocks for the construction of phosphotyrosine mimetics
  作者：G. Stuart Cockerill、Howard J. Easterfield、Jonathan M. Percy、Stéphane Pintat

  DOI：10.1039/b004187o

  日期：——

  The copper-catalysed zinc phosphonate chemistry described by Yokomatsu and Shibuya can be used to enter the classical organometallic coupling repertoire via Stille and Suzuki–Miyaura couplings. 1,4-Diiodobenzene underwent coupling with the organozinc reagent derived from diethyl bromodifluoromethylphosphonate with copper(I) catalysis to afford diethyl (4-iodophenyl)difluoromethylphosphonate. Higher yielding couplings were run with (4-trifluoromethylsulfonyloxy)- and (4-nonafluorobutylsulfonyloxy)-iodobenzenes. The iodide and the triflate coupled under palladium-catalysed conditions with a range of stannanes and boronic acids in moderate to excellent yields. Shibuya–Yokomatsu couplings were also successful with more functionalised iodoarenes and heteroarenes presenting the important phosphate mimic on a range of scaffolds.

  横松和渋谷描述的铜催化锌膦酸酯化学可用于通过斯蒂尔（Stille）和铃木-宫浦（Suzuki-Miyaura）偶联反应进入经典的金属有机偶联反应领域。1,4-二碘苯在铜(I)催化下与由二乙基溴二氟甲基膦酸酯衍生的有机锌试剂发生偶联，生成二乙基(4-碘苯基)二氟甲基膦酸酯。与(4-三氟甲磺酰氧基)和(4-九氟丁磺酰氧基)碘苯进行的偶联反应产率更高。碘化物和三氟甲磺酸酯在钯催化条件下与一系列锡烷和硼酸发生偶联，产率从中等到优异。渋谷-横松偶联反应在具有更丰富官能团的碘芳烃和杂芳烃上也取得了成功，这些重要磷酸类似物被引入多种骨架上。
• Synthesis and biological evaluation of α,α-difluorobenzylphosphonic acid derivatives as small molecular inhibitors of protein-tyrosine phosphatase 1B
  作者：Tsutomu Yokomatsu、Tetsuo Murano、Ikuko Umesue、Shinji Soeda、Hiroshi Shimeno、Shiroshi Shibuya

  DOI：10.1016/s0960-894x(99)00027-x

  日期：1999.2

  series of alpha,alpha-difluorobenzylphosphonic acids having a hydrophobic functional group were prepared via the Stille coupling reaction from halogenated alpha,alpha-difluorobenzylphosphonates. Evaluation of inhibitory activity toward protein tyrosine phosphatase (PTP 1B) revealed that the ethynyl, phenylethynyl and (E)-styryl groups on the benzene nuclei increased the inhibitory activity of alpha,alph

  通过Stille偶联反应，由卤化的α，α-二氟苄基膦酸酯制备了一系列具有疏水性官能团的α，α-二氟苄基膦酸。对蛋白酪氨酸磷酸酶（PTP 1B）的抑制活性的评估表明，苯核上的乙炔基，苯基乙炔基和（E）-苯乙烯基增加了α，α-二氟苄基膦酸的抑制活性。将（E）-苯乙烯基和双甲基磺酰胺官能团同时引入到α，α-二氟苄基膦酸的苯核上时，抑制活性显着提高。
• Copper-mediated oxidative difluoromethylenation of aryl boronic acids with α-silyldifluoromethylphosphonates: a new method for aryldifluorophosphonates
  作者：Xueliang Jiang、Lingling Chu、Feng-Ling Qing

  DOI：10.1039/c3nj00044c

  日期：——

  An unprecedented copper-mediated oxidative difluoromethylenation of aryl boronic acids with α-silyldifluoromethylphosphonates has been developed, allowing rapid access to a wide range of aryldifluorophosphonates containing various functional groups. This method provides a complementary and alternative method to Cu-mediated cross-couplings of aryl iodides with metalated difluoromethylphosphonates.

  一种前所未有的铜介导的芳基硼酸与α-甲硅烷基二氟甲基膦酸酯的氧化二氟甲基化反应已经被开发出来，允许快速获得各种含有各种官能团的芳基二氟膦酸酯。该方法为铜介导的芳基碘化物与金属化二氟甲基膦酸酯的交叉偶联提供了一种补充和替代方法。