diethyl [(2-hydroxy-3-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 [(2-hydroxy-3-methoxyphenyl)(phenylamino)methyl]phosphonate
• 英文别名: 2-[Anilino-[diethoxy(oxido)phosphaniumyl]methyl]-6-methoxyphenol；2-[anilino-[diethoxy(oxido)phosphaniumyl]methyl]-6-methoxyphenol
• 化学式: C₁₈H₂₄NO₅P
• 分子量: 365.366
• InChiKey: BABTUDUHVICTKD-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：
  83
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  邻香草醛 、 苯胺 、 亚磷酸二乙酯 在 Amberlite-IR 120 作用下， 反应 0.03h， 以95%的产率得到diethyl [(2-hydroxy-3-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

• Amberlite-IR 120 catalyzed three-component synthesis of α-amino phosphonates in one-pot
  作者：Asish K. Bhattacharya、Kalpeshkumar C. Rana

  DOI：10.1016/j.tetlet.2008.02.102

  日期：2008.4

  A simple, efficient, and environmentally benign method for a three-component reaction of an amine, an aldehyde or a ketone, and diethyl phosphite catalyzed by Amberlite-IR 120 resin has been developed to afford α-amino phosphonates in high yields and short reaction times under solvent-free reaction conditions. The major advantages of the present method are good yields, inexpensive, ecofriendly and

  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。
• 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。
• 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.
• Reusable zinc oxide nanoflowers for the synthesis of α-aminophosphonates under solvent-free ultrasonication
  作者：Sarika Rasal、Shilpa Jain、Navinchandra G Shimpi

  DOI：10.1080/00397911.2018.1492724

  日期：2018.9.17

  A simple wet chemical method is used to prepare zinc oxide nanoflowers (ZnO NFs) which were subjected to various characterization techniques such as XRD, FTIR, UV-Vis, FE-SEM, and XPS. XRD pattern indicates pure, crystalline, and monodispersed form with hexagonal wurtzite phase. The 3-D flower shape morphology with hexagonal ZnO nanorods was confirmed in FE-SEM. The synthesized ZnO NFs was used to study catalytic behavior in Kabachnik-Fields reaction under controlled ultrasound cavitation technique. High surface-to-volume ratio of ZnO NFs and the effect of ultrasonication enhances the yield of -aminophosphonate. The catalyst was recycled and reused four times without any significant loss of its catalytic activity. Moreover, existing method becomes attractive and practical due to its easy, clean, fast, cost-effective, and eco-friendly procedure.[GRAPHICS].