diethyl (((4-formyl)phenyl)difluoromethyl)phosphonate | 189393-74-6

• 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 (((4-formyl)phenyl)difluoromethyl)phosphonate
• 英文别名: diethyl difluoro(4-formylphenyl)methylphosphonate；[Difluoro-(4-formyl-phenyl)-methyl]-phosphonic acid diethyl ester；Diethyl [difluoro(4-formylphenyl)methyl]phosphonate；4-[diethoxyphosphoryl(difluoro)methyl]benzaldehyde
• CAS: 189393-74-6
• 化学式: C₁₂H₁₅F₂O₄P
• 分子量: 292.219
• InChiKey: XKIFBBTWXXFDOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl (((4-formyl)phenyl)difluoromethyl)phosphonate 在 三甲基溴硅烷 、 三乙酰氧基硼氢化钠 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (Difluoro-{4-[(4-[1,2,3]thiadiazol-4-yl-benzylamino)-methyl]-phenyl}-methyl)-phosphonic acid
  参考文献：
  名称：

  Discovery and structure–activity relationships of novel sulfonamides as potent PTP1B inhibitors

  摘要：

  A series of novel sulfonamides containing a single difluoromethylene-phosphonate group were discovered to be potent inhibitors of protein tyrosine phosphatase 1B. Structure-activity relationships around the scaffold were investigated, leading to the identification of compounds with IC50 or K-i values in the low nanomolar range. These sulfonamide-based inhibitors exhibit 100 and 30 times higher inhibitory activity than the corresponding tertiary amines and carboxamides, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.061
• 作为产物：
  描述：

  diethyl (difluoro(p-tolyl)methyl)phosphonate 在 N-溴代丁二酰亚胺(NBS) 、 乌洛托品 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 氯仿 为溶剂， 生成 diethyl (((4-formyl)phenyl)difluoromethyl)phosphonate
  参考文献：
  名称：

  Discovery and structure–activity relationships of novel sulfonamides as potent PTP1B inhibitors

  摘要：

  A series of novel sulfonamides containing a single difluoromethylene-phosphonate group were discovered to be potent inhibitors of protein tyrosine phosphatase 1B. Structure-activity relationships around the scaffold were investigated, leading to the identification of compounds with IC50 or K-i values in the low nanomolar range. These sulfonamide-based inhibitors exhibit 100 and 30 times higher inhibitory activity than the corresponding tertiary amines and carboxamides, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.061

文献信息

• 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。
• Nickel and Copper Catalyzed <i>ipso</i> ‐Phosphonodifluoromethylation of Arylboronic Acids with BrCF ₂ P(O)(OEt) ₂ for the Synthesis of Phosphonodifluoromethylarenes
  作者：Alexander Knieb、Vinayak Krishnamurti、Xanath Ispizua‐Rodriguez、G. K. Surya Prakash

  DOI：10.1002/chem.202200457

  日期：2022.7.20

  The presented method allows the preparation of ipso-phosphonodifluoromethylarenes utilizing a heterobimetallic catalytic system of nickel and copper. The protocol represents an advantage over traditional palladium catalysed Suzuki coupling due to the short reaction times and the use of earth-abundant metals.

  所提出的方法允许利用镍和铜的异质双金属催化体系制备异膦酰基二氟甲基芳烃。由于反应时间短和使用地球上丰富的金属，该协议比传统的钯催化 Suzuki 耦合具有优势。
• 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。
• Synthesis of N-Fmoc-4-[(diethylphosphono)-2′,2′-difluoro-1′-hydroxyethyl]phenylalanine, a novel phosphotyrosyl mimic for the preparation of signal transduction inhibitory peptides
  作者：Svitlana Chetyrkina、Karine Estieu-Gionnet、Georges Laı̈n、Mireille Bayle、Gérard Déléris

  DOI：10.1016/s0040-4039(00)00045-9

  日期：2000.3

  The synthesis of a novel non-hydrolyzable phosphotyrosyl mimic N-Fmoc-4-[(diethylphosphono)-2',2'-difluoro-1'-hydroxyethyl]-DL-phenylalanine is reported. (C) 2000 Elsevier Science Ltd. All rights reserved.
• US5922697A
  申请人：——

  公开号：US5922697A

  公开（公告）日：1999-07-13