diethyl α-[N-(4-hydroxyphenyl)amino]-α-(3,4-methylenedioxophenyl)methylphosphonate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: diethyl α-[N-(4-hydroxyphenyl)amino]-α-(3,4-methylenedioxophenyl)methylphosphonate
• 英文别名: 4-[[1,3-Benzodioxol-5-yl(diethoxyphosphoryl)methyl]amino]phenol
• 化学式: C₁₈H₂₂NO₆P
• 分子量: 379.35
• InChiKey: OOQSWXYUDOVDFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  胡椒醛 、 对氨基苯酚 、 亚磷酸二乙酯 在 Amberlite-IR 120 作用下， 反应 0.05h， 以98%的产率得到diethyl α-[N-(4-hydroxyphenyl)amino]-α-(3,4-methylenedioxophenyl)methylphosphonate
  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 Auto-catalyzed Mannich-TypeReaction for Synthesis of Highly Substituted­ α-Aminomethylphosphonates
  作者：Rifang Yang、Rusheng Zhao、Lizhi Zhao、Liuhong Yun、Hai Wang

  DOI：10.1055/s-2003-38679

  日期：——

  It has been found that a Mannich-type reaction catalyzed by an intramolecular phenolic hydroxy group involves simply heating a hydroxybenzaldehyde with a secondary amine and a dialkyl phosphite in alcohol, produced highly substituted α-aminomethylphosphonates. The corresponding reaction can hardly be detected if the hydoxy group of the benzaldehyde is absent or blocked, or the hydroxybenzaldehyde is replaced by 2′-hydroxyacetophenone.

  研究发现，由分子内酚羟基催化的Mannich型反应，仅需将羟基苯甲醛与二级胺和双烷基磷酸酯在醇中加热便可进行，产生高度取代的α-氨基甲基磷酸酯。如果苯甲醛的羟基缺失或被阻挡，或者羟基苯甲醛被2'-羟基乙酰苯替代，则相应的反应几乎无法检测到。
• Three component coupling catalyzed by TaCl5–SiO2: synthesis of α-amino phosphonates
  作者：S Chandrasekhar、S.Jaya Prakash、V Jagadeshwar、Ch Narsihmulu

  DOI：10.1016/s0040-4039(01)01053-x

  日期：2001.8

  TaCl5-SiO2 has been utilized as an efficient Lewis acid catalyst for the three component coupling of carbonyl compounds, aromatic amines and diethyl phosphite to produce a-amino phosphonates. (C) 2001 Published by Elsevier Science Ltd.
• 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.