diethyl [(3-hydroxy-4-methoxyphenyl)(phenylamino)methyl]phosphonate

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: diethyl [(3-hydroxy-4-methoxyphenyl)(phenylamino)methyl]phosphonate
• 英文别名: 5-[Anilino(diethoxyphosphoryl)methyl]-2-methoxyphenol；5-[anilino(diethoxyphosphoryl)methyl]-2-methoxyphenol
• 化学式: C₁₈H₂₄NO₅P
• 分子量: 365.366
• InChiKey: SSYQGKJEKGYGMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  77
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  异香兰素 、 苯胺 、 亚磷酸二乙酯 在 Amberlite-IR 120 作用下， 反应 0.03h， 以87%的产率得到diethyl [(3-hydroxy-4-methoxyphenyl)(phenylamino)methyl]phosphonate
  参考文献：
  名称：

  一锅内Amberlite-IR 120催化α-氨基膦酸酯的三组分合成

  摘要：

  已开发出一种简单，有效且环境友好的方法，用于由Amberlite-IR 120树脂催化的胺，醛或酮与亚磷酸二乙酯的三组分反应，从而以高收率和短反应时间提供α-氨基膦酸酯无溶剂反应条件下的反应时间。本方法的主要优点是产率高，价格便宜，生态友好且可重复使用的催化剂，温和且无溶剂的反应条件以及对基质中存在的各种功能的耐受性。

  DOI：

  10.1016/j.tetlet.2008.02.102

文献信息

• An Efficient One-Pot Synthesis of α-Amino Phosphonates Catalyzed by Bismuth Nitrate Pentahydrate
  作者：Asish Bhattacharya、Tanpreet Kaur

  DOI：10.1055/s-2007-970762

  日期：2007.3

  A simple, efficient, and environmentally benign method has been developed for the synthesis of α-amino phosphonates through a one-pot reaction of aldehydes with amines and diethyl phosphite in the presence of bismuth nitrate pentahydrate as a catalyst. Some of the major advantages of this protocol are: good yields, the involvement of a less-expensive and non-toxic catalyst, mild and solvent-free reaction conditions and also tolerance towards other functional groups present in the substrates. Eighteen examples are described, highlighting the substrate scope of the reaction.

  在五水硝酸铋作为催化剂的存在下，通过醛与胺和亚磷酸二乙酯的一锅反应合成δ-氨基膦酸盐，开发出了一种简单、高效且对环境无害的方法。该方法的一些主要优点包括：产率高、使用的催化剂成本较低且无毒、反应条件温和且无溶剂、对底物中存在的其他官能团具有耐受性。本文介绍了 18 个实例，突出了该反应的底物范围。
• 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.