diethyl [1,3-benzodioxol-5-yl(phenylamino)methyl]phosphonate

• 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 [1,3-benzodioxol-5-yl(phenylamino)methyl]phosphonate
• 英文别名: diethyl (benzo[d][1,3]dioxol-5-yl(phenylamino)methyl)phosphonate；N-[1,3-benzodioxol-5-yl(diethoxyphosphoryl)methyl]aniline
• 化学式: C₁₈H₂₂NO₅P
• 分子量: 363.35
• InChiKey: LGYVUXMSMGUEOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 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：
  66
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3,4-亚甲二氧基苄烯苯胺 、 亚磷酸三乙酯 在 水 作用下， 生成 diethyl [1,3-benzodioxol-5-yl(phenylamino)methyl]phosphonate
  参考文献：
  名称：

  烷基亚磷酸酯与 α,β-不饱和腈、茴香和由芳香醛衍生的肟的反应

  摘要：

  摘要 亚磷酸二烷基酯 (DAP, 1a, b) 和亚磷酸三烷基酯 (TAP, 2a, b) 与 α,β-不饱和腈（3a, b 和 4a, b）以及衍生的苯胺（5a 和 6）的反应来自芳香醛（香兰素和/或胡椒醛）的报道。新膦酸酯产品（参见 7、8、15、16 和 17）的结构基于兼容的元素和光谱结果 三价亚磷酸酯（TAP、2a、b）和三苯基膦将香草醛肟（5b）转化为 4-羟基 - 3-甲氧基苄腈 (19)。还假设了可能的反应机制来解释化合物 7a-d、8a、b 和 19 的形成。

  DOI：

  10.1080/10426509808035674

文献信息

• An organocatalyzed facile and rapid access to α-hydroxy and α-amino phosphonates under conventional/ultrasound technique
  作者：Pravin V. Shinde、Amol H. Kategaonkar、Bapurao B. Shingate、Murlidhar S. Shingare

  DOI：10.1016/j.tetlet.2011.03.138

  日期：2011.6

  irradiation for the rapid synthesis of α-hydroxy and α-amino phosphonates under solvent-free conditions is demonstrated. Use of a novel catalyst (i.e., camphor sulfonic acid) in combination with ultrasound technique is reported for the first time. Comparative study for the synthesis of α-hydroxy and α-amino phosphonates using conventional as well as ultrasonication method is discussed.

  在本工作中，证明了在无溶剂条件下成功实施超声辐射以快速合成α-羟基和α-氨基膦酸酯的方法。首次报道了将新型催化剂（樟脑磺酸）与超声技术结合使用。讨论了使用常规方法和超声方法合成α-羟基和α-氨基膦酸酯的比较研究。
• 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。
• 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.
• Tween-20: An Efficient Catalyst for One-Pot Synthesis of α-Aminophosphonates in Aqueous Media
  作者：Ch. Syama Sundar、D. Srinivasulu、S. K. Nayak、C. Suresh Reddy

  DOI：10.1080/10426507.2011.631641

  日期：2012.4.1

  A green one-pot three-component synthesis has been developed for alpha-aminophosphonates by condensation of aldehydes, amines, and diethylphosphite by using nonionic surfactant Tween-20 as catalyst in aqueous media. The results showed that this synthetic route for alpha-aminophosphonates takes just 25-60 min for completion at 60 degrees C and affords 64%-91% yields depending on the nature of the amine substrates. The major advantages of this novel method are green reaction conditions with water as solvent, simple workup, less reaction times, and high to moderate yields.