2-[[1,3-Benzodioxol-5-yl(diethoxyphosphoryl)methyl]amino]phenol | 1027103-94-1

• 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: 2-[[1,3-Benzodioxol-5-yl(diethoxyphosphoryl)methyl]amino]phenol
• 英文别名: 2-[[1,3-benzodioxol-5-yl(diethoxyphosphoryl)methyl]amino]phenol
• CAS: 1027103-94-1
• 化学式: C₁₈H₂₂NO₆P
• 分子量: 379.35
• InChiKey: APYSGRJHPGNLHI-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 、 亚磷酸二乙酯 、 2-氨基苯酚 在 Amberlite-IR 120 作用下， 反应 0.03h， 以79%的产率得到2-[[1,3-Benzodioxol-5-yl(diethoxyphosphoryl)methyl]amino]phenol
  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。
• 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.