二乙基[4-(氯甲基)苄基]膦酸酯 | 25596-72-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 二乙基[4-(氯甲基)苄基]膦酸酯
• 英文名称: diethyl <4-(chloromethyl)benzyl> phosphonate
• 英文别名: 4-(diethoxyphosphorylmethyl)benzylchloride；4-chloromethyl benzylphosphonate de diethyle；diethyl p-chloromethylbenzylphosphonate；diethyl 4-(chloromethyl)benzylphosphonate；1-(Chloromethyl)-4-(diethoxyphosphorylmethyl)benzene
• CAS: 25596-72-9
• 化学式: C₁₂H₁₈ClO₃P
• 分子量: 276.7
• InChiKey: CQUMASLUBXOYPU-UHFFFAOYSA-N

物化性质

• 沸点：
  170-175 °C(Press: 3 Torr)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  二乙基[4-(氯甲基)苄基]膦酸酯 在 乌洛托品 作用下， 以 溶剂黄146 为溶剂， 反应 3.0h， 以90%的产率得到4-(二乙基磷甲基)苯甲醛
  参考文献：
  名称：

  Oligo(phenylene vinylene)–poly(methylstyrene) hybrids: controlled step-wise molecular wiring of oligo(phenylene vinylene)

  摘要：

  Well defined oligo(phenylene vinylene) grafted polymers known as oligo(phenylene vinylene)-poly(methylstyrene) hybrids have been developed using a step-wise synthetic protocol, where the length of the OPV can be controlled systematically to achieve specific optoelectronic properties. The process allows the structural modification of attached OPV at a molecular level either by varying the chain length or by changing functionalities. The step-wise generation of OPV chains on the backbone of a highly soluble polymer ensures solubilization in a variety of solvents and also the exhibition of interesting optical properties. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.02.088
• 作为产物：
  描述：

  1,4-对二氯苄 、 亚磷酸三乙酯 反应 2.0h， 以48%的产率得到二乙基[4-(氯甲基)苄基]膦酸酯
  参考文献：
  名称：

  Efficient synthesis of small-sized phosphonated dendrons: potential organic coatings of iron oxide nanoparticles

  摘要：

  我们在此报道了一种生物相容性的、尺寸较小的膦酸化单体和树枝状大分子的合成，这些物质作为金属氧化物纳米颗粒的功能性涂层，更具体地说是用于磁共振成像（MRI）和通过高温治疗的铁磁性氧化物（SPIOs）。这些分子被设计用来调节它们的大小、亲水性和/或生物相容性特征（聚酰胺胺vs.寡聚乙二醇）、锚定的膦酸基团的数量（单膦酸vs.膦酸钳）以及外围功能性基团的数量，以便进一步接枝染料或特定的载体。这样一个亲水性膦酸库为研究作为治疗诊断一体化的树枝状纳米杂化物开辟了新的可能性。

  DOI：

  10.1039/c4nj00654b

文献信息

• INTESTINAL POLYP INHIBITOR
  申请人：JAPAN as represented by DIRECTOR GENERAL OF AGENCY OF NACIONAL CANCER CENTER

  公开号：EP1810681A1

  公开（公告）日：2007-07-25

  The present invention provides a medicine that has the effect of preventing the occurrence, inhibiting the progress and treatment of intestinal polyps that may develop into colon cancer, and relates to an intestinal polyp suppressor containing as an active component a carboxylic acid amide compound represented by the following General Formula: (wherein R is a lower alkyl group and X is a halogen), and in particular 4-diethoxyphosphinoylmethyl-N-(4-bromo-2-cyanophenyl)benzamide.

  本发明提供了一种具有预防可能发展为结肠癌的肠息肉的发生、抑制其进展和治疗效果的药物，涉及一种肠息肉抑制剂，其活性成分含有由下式通式表示的羧酸酰胺化合物： (其中 R 为低级烷基，X 为卤素），特别是 4-二乙氧基膦酰甲基-N-(4-溴-2-氰基苯基)苯甲酰胺。
• Synthesis and pharmacological study of new calcium antagonists, analogues of cinnarizine and flunarizine
  作者：S Younes、G Baziard-Mouysset、G de Saqui-Sannes、JL Stigliani、M Payard、R Bonnafous、J Tisne-Versailles

  DOI：10.1016/0223-5234(93)90049-k

  日期：1993.1

  Several phosphonic diethyl esters were synthesized and their calcium antagonistic activity evaluated in vitro. The diethyl phosphonate group was condensed on substituted [diphenylmethyl], [(2-benzofuranyl)phenylmethyl], [(4-(diphenylmethyl-1 piperazinyl) methyl], [4-(4-diphenylmethyl-1-piperazinyl methyl) phenylmethyl], and [4-(3-phenyl-2-propenyl)-1-piperazinyl methyl] groups. Despite the presence of the diethyl phosphonate moiety and the benzhydrylpiperazinyl group, both present in potent calcium antagonist structures, only 1 of the 19 synthesized compounds exhibited a calcium antagonistic profile.
• ω-haloalkylphosphoryl compounds: Synthesis and properties
  作者：V. V. Ragulin

  DOI：10.1134/s1070363212120055

  日期：2012.12

  A general method of the synthesis of omega-haloalkylphosphoryl compounds was developed, a series of compounds of phosphonic and phosphine oxide type were synthesized. The ability of some omega-haloalkylphosphonates to undergo intramolecular cyclization into the corresponding 1,2-oxaphospholane and 1,2-oxaphosphorine was investigated depending on the solvent polarity, the presence of halogen ions in the solution, and temperature. Tetrahydrofuran was chosen as one of the most suitable solvents for the alkylation of CH acids with omega-haloalkylphosphoryl compounds.
• Crystal structures of the apo form and a complex of human LMW-PTP with a phosphonic acid provide new evidence of a secondary site potentially related to the anchorage of natural substrates
  作者：Emanuella M.B. Fonseca、Daniela B.B. Trivella、Valéria Scorsato、Mariana P. Dias、Natália L. Bazzo、Kishore R. Mandapati、Fábio L. de Oliveira、Carmen V. Ferreira-Halder、Ronaldo A. Pilli、Paulo C.M.L. Miranda、Ricardo Aparicio

  DOI：10.1016/j.bmc.2015.06.017

  日期：2015.8

  Low molecular weight protein tyrosine phosphatases (LMW-PTP, EC 3.1.3.48) are a family of single-domain enzymes with molecular weight up to 18 kDa, expressed in different tissues and considered attractive pharmacological targets for cancer chemotherapy. Despite this, few LMW-PTP inhibitors have been described to date, and the structural information on LMW-PTP druggable binding sites is scarce. In this study, a small series of phosphonic acids were designed based on a new crystallographic structure of LMW-PTP complexed with benzylsulfonic acid, determined at 2.1 angstrom. In silico docking was used as a tool to interpret the structural and enzyme kinetics data, as well as to design new analogs. From the synthesized series, two compounds were found to act as competitive inhibitors, with inhibition constants of 0.124 and 0.047 mM. We also report the 2.4 angstrom structure of another complex in which LMW-PTP is bound to benzylphosphonic acid, and a structure of apo LMW-PTP determined at 2.3 angstrom resolution. Although no appreciable conformation changes were observed, in the latter structures, amino acid residues from an expression tag were found bound to a hydrophobic region at the protein surface. This regions is neighbored by positively charged residues, adjacent to the active site pocket, suggesting that this region might be not a mere artefact of crystal contacts but an indication of a possible anchoring region for the natural substrate-which is a phosphorylated protein. (C) 2015 Elsevier Ltd. All rights reserved.
• Évaluation de l'activité inhibitrice calcique d'une série de benzylphosphonates de diéthyle
  作者：G Tchani、G Baziard-Mouysset、S Younes、J Bellan、M Payard、JL Stigliani、G Grassy、R Bonnafous、J Tisne-Versailles

  DOI：10.1016/0223-5234(92)90120-p

  日期：1992.11

  Thirty-nine diethyl benzylphosphonates related to Fostedil were evaluated as calcium antagonists, using the inhibition test on aortic contraction in the rabbit, which was more selective than the negative inotropic activity test on guinea-pig left atrial muscle. Six compounds were found to have weak activity compared with Fostedil. Structure-activity relationships indicated a certain lipophilic influence; no correlation was found with electronic parameters. The prerequisite structure to obtain active products seems to require 2 conjugated aromatic rings separated by an optimal distance.