diethyl (2-(2,4-dichlorophenyl)2-oxoethyl)phosphonate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: diethyl (2-(2,4-dichlorophenyl)2-oxoethyl)phosphonate
• 英文别名: 1-(2,4-Dichlorophenyl)-2-diethoxyphosphorylethanone
• 化学式: C₁₂H₁₅Cl₂O₄P
• 分子量: 325.128
• InChiKey: CMPNUJIXIYYSDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 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：
  4

反应信息

• 作为反应物：
  描述：

  N,N-二甲基甲酰胺二甲基缩醛 、 diethyl (2-(2,4-dichlorophenyl)2-oxoethyl)phosphonate 以 甲苯 为溶剂， 反应 4.5h， 以89%的产率得到(E)-1-(2,4-dichlorophenyl)-2-diethoxyphosphoryl-3-(dimethylamino)prop-2-en-1-one
  参考文献：
  名称：

  Efficient syntheses of 3-phosphorylquinolin-4-ones and 3-phosphoryl-1,8-naphthyridin-4-ones

  摘要：

  A series of 3-diethoxyphosphorylquinolin-4-ones and 3-diethoxyphosphoryl-1,8-naphthyridin-4-ones containing various substituents at N-1 and C-7 was synthesized in a four-step reaction sequence starting from readily available ethyl 2-chlorobenzoates or ethyl 2-chloronicotinates and diethyl methylphosphonate. Selected quinolinone and naphthyridinone products were transformed into free mono and diacids. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.09.144
• 作为产物：
  描述：

  甲基膦酸二乙酯 、 2,4-二氯苯甲酸乙酯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 diethyl (2-(2,4-dichlorophenyl)2-oxoethyl)phosphonate
  参考文献：
  名称：

  Efficient syntheses of 3-phosphorylquinolin-4-ones and 3-phosphoryl-1,8-naphthyridin-4-ones

  摘要：

  A series of 3-diethoxyphosphorylquinolin-4-ones and 3-diethoxyphosphoryl-1,8-naphthyridin-4-ones containing various substituents at N-1 and C-7 was synthesized in a four-step reaction sequence starting from readily available ethyl 2-chlorobenzoates or ethyl 2-chloronicotinates and diethyl methylphosphonate. Selected quinolinone and naphthyridinone products were transformed into free mono and diacids. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.09.144

文献信息

• Solid Phase Acylation of Phosphonoacetates Synthesis of β-Keto Phosphonates from Polymer Bound Phosphonoacetate
  作者：Dae Young Kim、Ki Hyung Suh

  DOI：10.1080/00397919908086102

  日期：1999.4

  Abstract Solid phase synthesis of phase synthesis of β-keto phosphonates, via acylation reaction of polymer bound phosphoacetate with carboxylic acid chlorides in the presence of magnesium chloride-triethylamine followed by cleavage of resin with concomitant decarboxylation, is described.

  摘要 β-酮膦酸酯相合成的固相合成，在氯化镁-三乙胺的存在下，通过聚合物结合的磷酸乙酸酯与羧酸氯化物的酰化反应，随后树脂裂解并伴随脱羧作用，进行了描述。
• Anticancer properties of new synthetic hybrid molecules combining naphtho[2,3-b]furan-4,9-dione or benzo[f]indole-4,9-dione motif with phosphonate subunit
  作者：Katarzyna Gach、Jakub Modranka、Jacek Szymański、Dorota Pomorska、Urszula Krajewska、Marek Mirowski、Tomasz Janecki、Anna Janecka

  DOI：10.1016/j.ejmech.2016.05.002

  日期：2016.9

  3-diethoxyphosphorylnaphtho [2,3-b]furan-4,9-diones and 3-diethoxyphosphorylbenzo [f]indole-4,9-diones which integrate the natural 1,4-naphtalenedione scaffold, present in several anticancer agents with the phosphonate moiety. The cytotoxicity of such hybrid molecules was tested against two leukemia cell lines, HL-60 and NALM-6 and against a breast adenocarcinoma MCF-7 cell line. Selected compounds were also tested

  在本文中，我们报告了一种有效的一般合成的取代的3-二乙氧基磷酰萘并[2,3- b ]呋喃-4,9-二酮和3-二乙氧基磷酰苯并[ f ]吲哚-4,9-二烯结合了天然的1,4 -萘二甲酮骨架，存在于具有膦酸酯部分的几种抗癌剂中。测试了这种杂合分子对两种白血病细胞系HL-60和NALM-6以及对乳腺腺癌MCF-7细胞系的细胞毒性。所选化合物也已在正常人细胞：HUVEC和MCF-10A上进行了测试。通常，萘并呋喃-4,9-二酮比苯并吲哚-4,9-二酮显示出更高的细胞毒活性（IC 50值低于10μM）。最有希望的2-（2-氯苯基）-3-二乙氧基磷酰基萘[2,3- b选择了MTT试验中具有最高细胞毒性的]呋喃-4,9-二酮用于进一步评估其抗癌潜力。该化合物在HL-60和MCF-7细胞上进行了测试，可抑制细胞增殖，产生DNA损伤并诱导细胞凋亡。其细胞毒性活性的提示机制是细胞内活性氧的产生和线粒体膜电位耗散的诱导。
• Efficient syntheses of 3-phosphorylquinolin-4-ones and 3-phosphoryl-1,8-naphthyridin-4-ones
  作者：Jacek Kędzia、Jakub Modranka、Tomasz Janecki

  DOI：10.1016/j.tetlet.2011.09.144

  日期：2011.12

  A series of 3-diethoxyphosphorylquinolin-4-ones and 3-diethoxyphosphoryl-1,8-naphthyridin-4-ones containing various substituents at N-1 and C-7 was synthesized in a four-step reaction sequence starting from readily available ethyl 2-chlorobenzoates or ethyl 2-chloronicotinates and diethyl methylphosphonate. Selected quinolinone and naphthyridinone products were transformed into free mono and diacids. (C) 2011 Elsevier Ltd. All rights reserved.