(+/-)-dimethyl hydroxy(2-methoxyphenyl)methylphosphonate | 38706-95-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (+/-)-dimethyl hydroxy(2-methoxyphenyl)methylphosphonate
• 英文别名: Dimethoxyphosphoryl-(2-methoxyphenyl)methanol
• CAS: 38706-95-5
• 化学式: C₁₀H₁₅O₅P
• 分子量: 246.2
• InChiKey: UPJVDQVHFSKCRG-UHFFFAOYSA-N

物化性质

• 沸点：
  384.6±42.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+/-)-dimethyl hydroxy(2-methoxyphenyl)methylphosphonate 在 sodium hydroxide 、 四丁基溴化铵 、 三乙胺 作用下， 以 氯仿 、 水 为溶剂， 反应 10.0h， 生成
  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
• 作为产物：
  描述：

  亚磷酸二甲酯 、 邻甲氧基苯甲醛 在 phosphotungstic acid supported on silica-coated magnetic Fe₃O₄ nanoparticle 作用下， 以 neat (no solvent) 为溶剂， 反应 6.25h， 以96%的产率得到(+/-)-dimethyl hydroxy(2-methoxyphenyl)methylphosphonate
  参考文献：
  名称：

  磁性Fe3O4纳米颗粒负载的磷钨酸可在无溶剂条件下作为可再生催化剂用于Isbach，Imines和醛类的Kabachnik-Fields反应

  摘要：

  磁性纳米颗粒负载的磷钨酸已被用于以亚磷酸二甲酯和亚磷酸二乙酯为亲核试剂，有效地催化靛红，亚胺和醛的加氢膦酰化反应，从而在宽范围内以优异的收率得到相应的α-羟基和α-氨基膦酸酯。的基板。反应条件简单，绿色，高效。在保持活性的情况下，将催化剂再循环至五次。基于NMR光谱学研究，提出了可能的催化循环。

  DOI：

  10.1002/cplu.201402191

文献信息

• Synthesis and anticancer cytotoxicity with structural context of an α-hydroxyphosphonate based compound library derived from substituted benzaldehydes
  作者：Zita Rádai、Tímea Windt、Veronika Nagy、András Füredi、Nóra Zsuzsa Kiss、Ivan Ranđelović、József Tóvári、György Keglevich、Gergely Szakács、Szilárd Tóth

  DOI：10.1039/c9nj02144b

  日期：——

  active clusters, which encouraged us to synthesize further dibenzyl-α-diphenyl-OPP derivatives that elicited pronounced cell killing. Further structure–activity relationships showed the relevance of hydrophobicity and the position of substituents on the main benzene ring as determinants of toxicity. The most active analogs proved to be equally, or even more toxic to the multidrug resistant (MDR) cell line

  我们合成了取代的苯甲醛衍生的α-羟基膦酸酯（αOHP），α-羟基膦酸（αOHPA）和α-膦酰氧基膦酸酯（αOPP），并表征了它们对一组癌细胞系的细胞毒性。使用基于荧光的细胞毒性试验，针对Mes-Sa亲本和Mes-Sa / Dx5多药耐药子宫肉瘤细胞系筛选了包含56个类似物的文库。细胞毒性筛选显示，二苄基-αOHP和二甲基-α-二苯基-OPP是最活跃的簇，这鼓励我们合成进一步的二苄基-α-二苯基-OPP衍生物，引起明显的细胞杀伤作用。进一步的结构-活性关系显示疏水性和主苯环上取代基的位置与毒性有关。事实证明，最活跃的类似物是同等的，
• Synthesis and Antimicrobial Activity of Bisphosphonates
  作者：M. Veera Narayana Reddy、K.R. Kishore Kumar Reddy、C. Bhupendra Reddy、B. Siva Kumar、C. Suresh Reddy、C. Devendranath Reddy

  DOI：10.3184/030823409x439744

  日期：2009.4

  Dimethyl [(substitutedphenyl)(6-oxo6λ⁵dibenzo[ d,f][1,3,2]dioxaphophepin-6-yl)methyl]phosphonates (5a-j) were synthesised through a three step process involving preparation of dimethyl hydroxy(substitutedphenyl)methyl-phosphonates (4a-j) and their reaction with 6-bromodibenzo[ d,f][1,3,2]dioxaphosphepine (2) in dry toluene in the presence of triethylamine at 50–60°C. Tetramethylguanidine (TMG) as a catalyst was found to increase the yields and purity of the products. These compounds were characterised by IR, ¹H, ¹³C, ³¹P NMR and mass spectral data found to possess higher antimicrobial activity then the standards.

  二甲基[(取代苯基)(6-氧代 6λ5 二苯并[d,f][1,3,2]二氧杂环庚烷-6-基)甲基]膦酸盐 (5a-j) 通过三步法合成，包括制备二甲基羟基(取代苯基)甲基膦酸盐 (4a-j)，并与 6-溴二苯并[d、f][1,3,2]二氧磷杂菲（2）的反应。作为催化剂的四甲基胍（TMG）提高了产品的产量和纯度。通过红外光谱、1H、13C、31P NMR 和质谱数据对这些化合物进行表征，发现它们比标准物质具有更高的抗菌活性。
• Superparamagnetic magnesium ferrite nanoparticles: a magnetically reusable and clean heterogeneous catalyst
  作者：Mehdi Sheykhan、Hossein Mohammadnejad、Jafar Akbari、Akbar Heydari

  DOI：10.1016/j.tetlet.2012.03.069

  日期：2012.6

  A highly efficient magnetically recoverable nano-catalyst was fabricated. The material synthesized has been fully characterized by vibrating sample magnetometry (VSM), X-ray powder diffraction, scanning and transmission electron microscopy, FT-IR, and the Brunauer-Emmett-Teller (BET) isotherm method. An investigation of its catalytic activity showed it to be a unique heterogeneous Lewis acid catalyst for the synthesis of alpha-hydroxy and alpha-aminophosphonates, giving a total turnover number >= 450 for five consecutive runs. The catalyst is superparamagnetic having a 'magnetization (left behind after an external magnetic field is removed)' to 'magnetic saturation' ratio of about 0.0008, and thus could be easily separated by the use of an external magnetic field and was not agglomerated by exposure to magnetic fields. (C) 2012 Elsevier Ltd. All rights reserved.
• Organic catalysis of phospha-aldol condensation
  作者：A. O. Kolodyazhnaya、V. P. Kukhar、O. I. Kolodyazhnyi

  DOI：10.1134/s1070363208110091

  日期：2008.11

  Phospha-aldol reaction of dialkylphosphites with carbonyl compounds is catalyzed by cinchonine alkaloids and thier modified derivatives to give optically active hydroxyphosphonates. The use of diastereomeric pairs of alkaloids allowed obtaining both optical antipodes of hydroxyphosphonates. Cinchonine alkaloids show the highest enantioselectivity as organic catalysts. It was found that ordinary crystallization of some enantiomerically enriched hydroxyphosphonates leads to isolation of the enantiomerically pure stereoisomers. Hydroxyphosphonic acids were obtained by hydrolysis of phosphonates. Fluoroalkylphosphonates were obtained by reaction with diethylaminotrifluorosulfurane (DAST).
• Synthesis and insecticidal activities of <i>O,O</i>-dialkyl-2-[3-bromo-1-(3-chloropyridin-2-yl)-1<i>H</i>-pyrazole-5-carbonyloxy] (aryl) methylphosphonates
  作者：Wei Wang、Lie-Ping Wang、Bin-Ke Ning、Ming-Zhen Mao、Chao Xue、Hai-Yang Wang

  DOI：10.1080/10426507.2016.1206103

  日期：2016.10.2

  A series of novel O,O-Dialkyl-2-[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonyloxy](aryl) methy-lphosphonates I-1-14 were designed and synthesized. The structures of all the title compounds were confirmed by H-1-NMR, C-13-NMR, P-31-NMR, IR and elemental analysis. Their insecticidal activities against Mythimna separata and Plutella xylostella were evaluated. The results of bioassays indicated that the title compounds exhibited 20-80% larvicidal activity against Mythimna separata at 1000mg/L.[GRAPHICS].