diethyl 4-phenoxyphenylphosphonate | 77918-43-5

• 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 4-phenoxyphenylphosphonate
• 英文别名: 4-phenoxyphenylphosphonic acid diethyl ester；diphenyl ether-4-phosphonic acid diethyl ester；Phosphonic acid, (4-phenoxyphenyl)-, diethyl ester；1-diethoxyphosphoryl-4-phenoxybenzene
• CAS: 77918-43-5
• 化学式: C₁₆H₁₉O₄P
• 分子量: 306.298
• InChiKey: GWRKZKPLBKOUMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl 4-phenoxyphenylphosphonate 在 N-甲基吗啉 、 O-(三甲基硅)羟胺 、 五氯化磷 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (+/-)-2-Oxo-2-(4-phenoxyphenyl)-1,3,2-oxazaphosphorocane-3-acetohydroxamic acid
  参考文献：
  名称：

  环磷酰胺和膦酰胺，一系列新型的具有抗肿瘤活性的有效基质金属蛋白酶抑制剂。

  摘要：

  介绍了一系列新型非肽环状膦和次膦酰胺基异羟肟酸作为基质金属蛋白酶MMP-1，MMP-3和MMP-9的抑制剂的设计，合成和结构活性关系（SAR）。基于建模研究和X射线分析，获得了这些新型化合物在MMP活性位点的结合模式的模型。该模型为观察到的SAR数据提供了合理的解释，其中包括对不同的S1'定向取代基，锌络合基团，手性以及环状膦和次膦酰胺环的变化进行的系统研究。评价了四种化合物在人纤维肉瘤小鼠模型（HT1080）中的体内作用，并将其与参考化合物Prinomastat的体内作用进行了比较。对于所有四种化合物均观察到肿瘤生长的抑制。

  DOI：

  10.1016/j.bmc.2003.09.015
• 作为产物：
  描述：

  亚磷酸三乙酯 、 4-溴联苯醚 在 1,3-二异丙基苯 、 nickel dibromide 作用下， 反应 48.0h， 生成 diethyl 4-phenoxyphenylphosphonate
  参考文献：
  名称：

  JP5664635

  摘要：

  公开号：

文献信息

• Palladium anchored on a covalent organic framework as a heterogeneous catalyst for phosphorylation of aryl bromides
  作者：Yu‐Xuan Chen、Shuo Zhang、Yu‐Jie Xue、Li‐Ping Mo、Zhan‐Hui Zhang

  DOI：10.1002/aoc.6480

  日期：2022.1

  A simple azine-linked covalent organic framework (COF) with high thermal and chemical stabilities has been prepared by using deep eutectic solvent (DES) as green media. The as-synthesized COF was employed as heterogeneous ligand for immobilization of PdII. The obtained Pd-supported COF nanoparticles catalyst (defined as Pd/TFPT-Azine-COF) was found to be an efficient heterogeneous catalyst for the

  以低共熔溶剂（DES）为绿色介质，制备了一种简单的具有高热稳定性和化学稳定性的吖嗪连接的共价有机骨架（COF）。合成后的 COF 用作固定 Pd II的非均相配体。发现所获得的 Pd 负载 COF 纳米颗粒催化剂（定义为 Pd/TFPT-Azine-COF）是一种高效的多相催化剂，用于芳基卤化物和亚磷酸二烷基酯或二苯基氧化膦的 Hirao 反应，具有优异的可回收性、可重复使用性和结晶度保持性.
• Thianthrenium-Enabled Phosphorylation of Aryl C–H Bonds via Electron Donor–Acceptor Complex Photoactivation
  作者：Hao Xu、Xufeng Li、Yuzheng Dong、Shuangran Ji、Junze Zuo、Jian Lv、Daoshan Yang

  DOI：10.1021/acs.orglett.3c01303

  日期：2023.5.26

  An efficient strategy for the preparation of aryl phosphonates via blue-light-promoted single electron transfer process of an EDA complex between phosphites and thianthrenium salts has been demonstrated. The corresponding substituted aryl phosphonates were obtained in good to excellent yields, and the byproduct thianthrene can be recovered and reused in quantity. This developed method realizes the

  已经证明了通过亚磷酸盐和噻蒽盐之间的 EDA 络合物的蓝光促进单电子转移过程制备芳基膦酸盐的有效策略。相应的取代芳基膦酸酯以良好的收率获得，并且副产物噻蒽可以大量回收和再利用。该方法通过芳烃的间接C-H功能化实现了芳基膦酸酯的构建，在药物发现和开发中具有潜在的应用价值。
• Electrochemical Generation of Aryl Radicals from Organoboron Reagents Enabled by Pulsed Electrosynthesis
  作者：Maxime Boudjelel、Jessica Zhong、Lorenzo Ballerini、Ian Vanswearingen、Rossul Al‐Dhufari、Christian A. Malapit

  DOI：10.1002/anie.202406203

  日期：2024.7.29

  Pulsed electrosynthesis efficiently converts aromatic organoboron reagents to aryl radicals. Mechanistic studies reveal that pulsed electrosynthesis overcomes challenges like radical grafting/passivation, homocoupling, overoxidation, and decomposition. This electro-oxidative method enables straightforward functionalization of aromatic organoboron reagents to form aryl C−P, C−Se, C−Te, and C−S bonds

  脉冲电合成有效地将芳香族有机硼试剂转化为芳基自由基。机理研究表明，脉冲电合成克服了自由基接枝/钝化、自偶联、过度氧化和分解等挑战。这种电氧化方法能够直接官能化芳香族有机硼试剂，形成芳基 C−P、C−Se、C−Te 和 C−S 键。
• New Type of Metalloproteinase Inhibitor:  Design and Synthesis of New Phosphonamide-Based Hydroxamic Acids
  作者：Masaaki Sawa、Takao Kiyoi、Kiriko Kurokawa、Hiroshi Kumihara、Minoru Yamamoto、Tomohiro Miyasaka、Yasuko Ito、Ryoichi Hirayama、Tomomi Inoue、Yasuyuki Kirii、Eiji Nishiwaki、Hiroshi Ohmoto、Yu Maeda、Etsuko Ishibushi、Yoshimasa Inoue、Kohichiro Yoshino、Hirosato Kondo

  DOI：10.1021/jm0103211

  日期：2002.2.1

  A series of phosphonamide-based hydroxamate derivatives were synthesized, and the inhibitory activities were evaluated against various metalloproteinases in order to clarify its selectivity profile. Among the four diastereomeric isomers resulting from the chirality at the C-3 and P atoms, the compound with a (R,R)-configuration both at the C-3 position and the phosphorus atom was found to be potently active, while the other diastereomeric isomers were almost inactive. A number of (R,R)-compounds synthesized here exhibited broad spectrum activities with nanomolar K-i values against MMP-1, -3, -9, and TACE and also showed nanomolar IC50 values against HB-EGF shedding in a cell-based inhibition assay. The modeling study using X-ray structure of MMP-3 suggested the possible binding mode of the phosphonamide-based inhibitors.
• Grabiak, Raymond C.; Miles, James A.; Schwenzer, Gretchen M., Phosphorus and Sulfur and the Related Elements, 1980, vol. 9, p. 197 - 202
  作者：Grabiak, Raymond C.、Miles, James A.、Schwenzer, Gretchen M.

  DOI：——

  日期：——