diethyl [(3,4-dichlorophenyl)(hydroxy)methyl]phosphonate | 389829-69-0

• 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 [(3,4-dichlorophenyl)(hydroxy)methyl]phosphonate
• 英文别名: Diethyl (3,4-dichloro-alpha-hydroxybenzyl)phosphonate；(3,4-dichlorophenyl)-diethoxyphosphorylmethanol
• CAS: 389829-69-0
• 化学式: C₁₁H₁₅Cl₂O₄P
• 分子量: 313.117
• InChiKey: WHZVWBKGYWFUEV-UHFFFAOYSA-N

物化性质

• 沸点：
  418.5±45.0 °C(Predicted)
• 密度：
  1.356±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 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：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl [(3,4-dichlorophenyl)(hydroxy)methyl]phosphonate 在 盐酸 、 水 作用下， 生成 ((3,4-dichlorophenyl)(hydroxy)methyl)phosphonic acid
  参考文献：
  名称：

  针对细菌细胞生长的类异戊二烯生物合成抑制剂

  摘要：

  我们合成了法尼基二磷酸合酶 (FPPS)、十一异戊二烯基二磷酸合酶 (UPPS) 或十一异戊二烯基二磷酸磷酸酶 (UPPP) 的潜在抑制剂，并在细菌细胞生长和酶抑制测定中对其进行了测试。发现最活跃的化合物是具有吸电子芳基烷基侧链的双膦酸盐，在~1-4 μg mL -1时可抑制革兰氏阴性菌（鲍曼不动杆菌、肺炎克雷伯菌、大肠杆菌和铜绿假单胞菌）的生长。水平。它们被发现是 FPPS 的有效抑制剂；添加金合欢醇或过度表达 FPPS 可以部分“挽救”细胞生长，并且与已知的类异戊二烯生物合成途径抑制剂具有协同活性。亲脂性羟烷基膦酸在微摩尔水平上抑制 UPPS 和 UPPP；它们对革兰氏阳性生物体有活性（∼2-6 μg mL -1），但对革兰氏阴性生物体没有活性，并且再次表现出与细胞壁生物合成抑制剂的协同活性，但与其他抑制剂的作用无关紧要。结果很有趣，因为它们描述了 FPPS、UPPS 和 UPPP 的

  DOI：

  10.1002/cmdc.201600343
• 作为产物：
  描述：

  亚磷酸二乙酯 、 3,4-二氯苯甲醛 在 aluminum oxide 、 potassium fluoride 作用下， 生成 diethyl [(3,4-dichlorophenyl)(hydroxy)methyl]phosphonate
  参考文献：
  名称：

  含有 α-羟基膦酸酯的 5-氟尿嘧啶衍生物

  摘要：

  为了寻找高活性、低毒的抗肿瘤药物先导化合物，通过相合成法合成了 13 种新型 N1-(2-呋喃基)-N3-(O,O-二烷基膦酰基芳基(烷基)甲氧基-羰基甲基)-5-氟尿嘧啶。氯乙酰氧基烷基膦酸酯 2 与 N1-（2-呋喃基）-5-氟尿嘧啶的转移催化反应。产物的结构经1H NMR、31P NMR、IR、MS谱和元素分析确证。初步生物测定结果表明新化合物对HCT-8和Bel-7402细胞系具有一定程度的抑制作用和良好的杀菌活性。

  DOI：

  10.1080/10426500600919975

文献信息

• The Synthesis and Herbicidal Evaluation of Fluorine-Containing Phenoxyacetoxyalkylphosphonate Derivatives
  作者：Ting Chen、Ping Shen、Yanjun Li、Hongwu He

  DOI：10.1080/10426500600614253

  日期：2006.9.1

  Compound 5l exhibited notable activity. Results showed that by introducing a fluorine moiety to the parent structure of phenoxyacetoxyalkylphosphonates, a series of new compounds with satisfactory herbicidal activity could be synthesized. A reasonable combination of a fluorine moiety and other substituents on the benzene ring had a great influence on the herbicidal activity.

  为了研究氟部分对苯氧基乙酰氧基烷基膦酸酯的生物活性的影响，合成了一系列含氟苯氧基乙酰氧基烷基膦酸酯并在温室中筛选了除草活性。大多数标题化合物对试验植物，尤其是单子叶植物，显示出比出苗后活性更好的出苗前活性。化合物5l表现出显着的活性。结果表明，通过在苯氧基乙酰氧基烷基膦酸酯的母体结构中引入氟基团，可以合成一系列具有令人满意的除草活性的新化合物。苯环上的氟部分和其他取代基的合理组合对除草活性有很大影响。
• Tailoring the Structure of Aminobisphosphonates To Target Plant P5C Reductase
  作者：Giuseppe Forlani、Andrea Occhipinti、Łukasz Berlicki、Gabriela Dziedzioła、Anna Wieczorek、Paweł Kafarski

  DOI：10.1021/jf800029t

  日期：2008.5.1

  Using the structure of (3,5-dichlorophenyl)aminomethylenebisphosphonic acid as a lead compound, 25 new phosphonates were synthesized and evaluated as possible inhibitors of Arabidopsis thaliana delta(1)-pyrroline-5-carboxylate (P5C) reductase. Derivatives substituted in the phenyl ring retained the inhibitory potential, though to a different extent. On the contrary any variation in the scaffold, i.e., the replacement of the second phosphonate moiety with a hydroxyl or an amino residue, resulted in a significant loss of biological activity. The availability of several structures capable of interfering with the catalytic mechanism in the micromolar to millimolar range allowed a proper structure-activity relationship analysis, leading us to hypothesize about the steric and electronic requirements for maintenance or enhancement of the inhibitory properties. Reversal experiments with suspension cultured cells provided evidence for the occurrence of enzyme inhibition in vivo. Because in higher plants the step catalyzed by P5C reductase is shared by all pathways leading to proline synthesis, these compounds may be exploited for the design of new substances endowed with herbicidal activity.
• α-Substituted β-Oxa Isosteres of Fosmidomycin: Synthesis and Biological Evaluation
  作者：Karin Brücher、Boris Illarionov、Jana Held、Serena Tschan、Andrea Kunfermann、Miriam K. Pein、Adelbert Bacher、Tobias Gräwert、Louis Maes、Benjamin Mordmüller、Markus Fischer、Thomas Kurz

  DOI：10.1021/jm300652f

  日期：2012.7.26

  Specific inhibition of enzymes of the non-mevalonate pathway is a promising strategy for the development of novel antiplasmodial drugs. alpha-Aryl-substituted beta-oxa isosteres of fosmidomycin with a reverse orientation of the hydroxamic acid group were synthesized and evaluated for their inhibitory activity against recombinant 1-deoxy-D-xylulose 5-phosphate reductoisomerase (IspC) of Plasmodium falciparum and for their in vitro antiplasmodial activity against chloroquine-sensitive and resistant strains of P. falciparum. The most active derivative inhibits IspC protein of P. falciparum (PfIspC) with an IC50 value of 12 nM and shows potent in vitro antiplasmodial activity. In addition, lipophilic ester prodrugs demonstrated improved P. falciparum growth inhibition in vitro.