diethyl (2-methoxyphenylamino)(p-tolyl)methylphosphonate | 1446321-18-1

• 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 (2-methoxyphenylamino)(p-tolyl)methylphosphonate
• 英文别名: N-[diethoxyphosphoryl-(4-methylphenyl)methyl]-2-methoxyaniline
• CAS: 1446321-18-1
• 化学式: C₁₉H₂₆NO₄P
• 分子量: 363.394
• InChiKey: YAMAVVAKQFIQRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对甲基苯甲醛 、 邻甲氧基苯胺 、 亚磷酸三乙酯 在 silica-coated MgAl₂O₄ nanoparticles supported phosphotungstic acid 作用下， 以 neat (no solvent) 为溶剂， 反应 0.33h， 以95%的产率得到diethyl (2-methoxyphenylamino)(p-tolyl)methylphosphonate
  参考文献：
  名称：

  Silica-coated MgAl2O4 nanoparticles supported phosphotungstic acid as an effective catalyst for synthesis of α-aminophosphonates

  摘要：

  本研究采用简单的利用方法制备了一种可回收催化剂（MgAl2O4@SiO2-PTA）。对制备的催化剂进行了 XRD、FT-IR、SEM、EDX、ICP-AES 和 BET 表征。根据 Debye-Scherrer 公式计算出 MgAl2O4 的平均晶粒尺寸为 40 nm 。该纳米复合材料作为一种异相催化剂，在室温无溶剂条件下用于合成α-氨基膦酸盐。在这一过程中，铝酸镁尖晶石（MgAl2O4）作为 H3PW12O40（PTA）的基质和支撑催化剂，可实现催化剂的循环和重复使用，同时由于表面/体积比的增加，也提高了反应的效率。为了获得最佳条件，研究人员使用不同的溶剂和催化剂研究了 α-氨基膦酸盐反应的合成。结果表明，与其他反应相比，苯甲醛和苯胺反应制备的 α-氨基膦酸盐具有更高的效率和更短的时间。催化剂可通过简单过滤回收，且可连续循环使用至少五次而不会丧失催化活性。

  DOI：

  10.1007/s11164-019-03737-z

文献信息

• Diversity-oriented synthesis of α-aminophosphonates: A new class of potential anticancer agents
  作者：Asish K. Bhattacharya、Dnyaneshwar S. Raut、Kalpeshkumar C. Rana、Innaiah K. Polanki、Mohd Sajid Khan、Sana Iram

  DOI：10.1016/j.ejmech.2013.05.036

  日期：2013.8

  A small library of structurally diverse alpha-aminophosphonates has been synthesized by reacting alkyl/aryl aldehydes, alkyl/aryl amines and alkyl/aryl phosphites in one-pot catalyzed by Amberlite-IR 120 resin (acidic). All the synthesized alpha-aminophosphonates were assayed for their in vitro cytotoxic activities against a panel of five human cancer cell lines including A-549, NCI-H23 (Lung), Colo 320DM (Colon), MG-63 (Bone marrow) and Jurkat (Blood T lymphocytes). Compound 4n having (R)-1-phenylethanamine was found to be the most active amongst all the synthesized alpha-aminophosphonates against all the five cancer cell lines, most prominent being against Jurkat cell line with an IC50 value of 4 mu M. Surprisingly, compound 4o having (S)-1-phenylethanamine was found to be devoid of any cytotoxicity. Our finding suggests that these chemical entities could further serve as interesting template for the design of potential anticancer agents. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Efficient Bakers’ Yeast-Catalyzed Multicomponent Synthesis of <font>α</font>-Aminophosphonates in One Pot
  作者：Asish K. Bhattacharya、Mohammad Mujahid

  DOI：10.1080/00397911.2012.721918

  日期：2013.10.2

  Utilizing bakers' yeast (Saccharomyces cerevisiae) as a biocatalyst, synthesis of -aminophosphonates in one pot has been accomplished by the three-component reaction of an aldehyde, an amine, and diethyl phosphite in moderate to good yields under solvent-free reaction conditions. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.
• Silica-coated MgAl2O4 nanoparticles supported phosphotungstic acid as an effective catalyst for synthesis of α-aminophosphonates
  作者：Reza Hajavazzade、Ali Reza Mahjoub、M. Kargarrazi

  DOI：10.1007/s11164-019-03737-z

  日期：2019.4

  In this research, a recoverable catalyst (MgAl2O4@SiO2–PTA) was prepared by a simple utilization method. The prepared catalyst was characterized by XRD, FT-IR, SEM, EDX, ICP-AES, and BET techniques. The average crystallite size of MgAl2O4 was calculated to be 40 nm by the Debye–Scherrer formula. The nanocomposite was examined as a heterogeneous catalyst for synthesis of α-aminophosphonates under solvent-free conditions at room temperature. In this process, magnesium aluminate spinel (MgAl2O4), used as the base and supporting catalyst for H3PW12O40 (PTA), provides the recycling and reusing of the catalyst and also increases the efficiency of the reaction, which is due to the increase in the surface/volume ratio. In order to obtain optimal conditions, the synthesis of α-aminophosphonates reactions was investigated with different solvents and catalysts. The results showed that α-aminophosphonate prepared from the benzaldehyde and aniline reaction has higher efficiency and a shorter time than other reactions. The catalyst was recovered by simple filtration, and it can be recycled for at least five successive times without loss of catalytic activity.

  本研究采用简单的利用方法制备了一种可回收催化剂（MgAl2O4@SiO2-PTA）。对制备的催化剂进行了 XRD、FT-IR、SEM、EDX、ICP-AES 和 BET 表征。根据 Debye-Scherrer 公式计算出 MgAl2O4 的平均晶粒尺寸为 40 nm 。该纳米复合材料作为一种异相催化剂，在室温无溶剂条件下用于合成α-氨基膦酸盐。在这一过程中，铝酸镁尖晶石（MgAl2O4）作为 H3PW12O40（PTA）的基质和支撑催化剂，可实现催化剂的循环和重复使用，同时由于表面/体积比的增加，也提高了反应的效率。为了获得最佳条件，研究人员使用不同的溶剂和催化剂研究了 α-氨基膦酸盐反应的合成。结果表明，与其他反应相比，苯甲醛和苯胺反应制备的 α-氨基膦酸盐具有更高的效率和更短的时间。催化剂可通过简单过滤回收，且可连续循环使用至少五次而不会丧失催化活性。