diethyl α,α-difluoro-2-nitrobenzylphosphonate | 177284-52-5

• 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 α,α-difluoro-2-nitrobenzylphosphonate
• 英文别名: diethyl [difluoro(2-nitrophenyl)methyl]phosphonate；[difluoro-(2-nitro-phenyl)-methyl]-phosphonic acid diethyl ester；(alpha,alpha-Difluoro-2-nitrobenzyl)phosphonic acid diethyl ester；1-[diethoxyphosphoryl(difluoro)methyl]-2-nitrobenzene
• CAS: 177284-52-5
• 化学式: C₁₁H₁₄F₂NO₅P
• 分子量: 309.206
• InChiKey: ULSAICDOXPGETA-UHFFFAOYSA-N

物化性质

• 沸点：
  388.0±42.0 °C(Predicted)
• 密度：
  1.331±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 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：
  81.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  diethyl α,α-difluoro-2-nitrobenzylphosphonate 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 8.5h， 生成 diethyl difluoro[2-(octanoylamino)phenyl]methylphosphonate
  参考文献：
  名称：

  Discovery of Novel Phosphonic Acid Derivatives as New Chemical Leads for Inhibitors of TNF-α production

  摘要：

  2-(Acylamino)betzylphosphonic acid 6 derived from an artificial substrate of sphingomyelinase was found to show inhibitory activity of TNF-alpha production. Structural optimization was started with the chemical modification of 6. The discovery of another chemical leads 7, 8, 10 and 16 for the development of structurally new inhibitors of TNF-alpha production is reported. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00343-7
• 作为产物：
  描述：

  2-硝基苄溴 在 sodium hexamethyldisilazane 、 N-氟代双苯磺酰胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 8.0h， 生成 diethyl α,α-difluoro-2-nitrobenzylphosphonate
  参考文献：
  名称：

  Discovery of Novel Phosphonic Acid Derivatives as New Chemical Leads for Inhibitors of TNF-α production

  摘要：

  2-(Acylamino)betzylphosphonic acid 6 derived from an artificial substrate of sphingomyelinase was found to show inhibitory activity of TNF-alpha production. Structural optimization was started with the chemical modification of 6. The discovery of another chemical leads 7, 8, 10 and 16 for the development of structurally new inhibitors of TNF-alpha production is reported. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00343-7

文献信息

• Copper-Mediated Introduction of the CF₂ PO(OEt)₂ Motif: Scope and Limitations
  作者：Maria V. Ivanova、Alexandre Bayle、Tatiana Besset、Xavier Pannecoucke、Thomas Poisson

  DOI：10.1002/chem.201703542

  日期：2017.12.6

  can be functionalised. The procedure allows the conversion of aryl diazonium salts, as well as aryl, heteroaryl, vinyl and alkynyl iodonium salts, into the corresponding fluorinated molecules at room temperature. Mechanistic studies were performed to gain a better understanding of the reaction pathway. Under similar conditions, vinyl and aryl iodides, allyl halides, and benzyl bromides were also functionalised

  在本文中，报告了访问包含CF 2 PO（OEt）2的分子的一般程序。试剂CuCF 2 PO（OEt）2可以通过简单的协议访问，并且可以对多种底物进行功能化。该方法允许在室温下将芳基重氮盐以及芳基，杂芳基，乙烯基和炔基碘鎓盐转化为相应的氟化分子。进行了机理研究，以更好地了解反应途径。在相似的条件下，乙烯基和芳基碘化物，烯丙基卤化物和苄基溴化物也被官能化，并且研究了反应的范围和局限性。最后，该程序扩展到二硫化物，以提供新的SCF 2通道含PO（OEt）2的分子。
• 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。
• 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。
• aSMase inhibitors
  申请人：Baumann Karl

  公开号：US20100022482A1

  公开（公告）日：2010-01-28

  The present invention relates to compounds of formula wherein the residues have various meanings and their use as pharmaceuticals.

  本发明涉及公式化合物，其中残基具有不同的含义，并将它们用作药物。
• WO2008/22771
  申请人：——

  公开号：——

  公开（公告）日：——