diisopropyl 2-amino-3-cyano-4H-chromen-4-ylphosphonate | 1422566-61-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: diisopropyl 2-amino-3-cyano-4H-chromen-4-ylphosphonate
• 英文别名: Diisopropyl 2-amino-3-cyano-4h-chromen-4-yl phosphonate；2-amino-4-di(propan-2-yloxy)phosphoryl-4H-chromene-3-carbonitrile
• CAS: 1422566-61-7
• 化学式: C₁₆H₂₁N₂O₄P
• 分子量: 336.327
• InChiKey: SYQXGBYMSZPUFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  94.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  亚磷酸二异丙酯 、 水杨醛 、 丙二腈 在 五甲基二乙烯三胺 作用下， 反应 0.5h， 以84%的产率得到diisopropyl 2-amino-3-cyano-4H-chromen-4-ylphosphonate
  参考文献：
  名称：

  PMDTA催化含有膦酸酯或氧化膦部分的2-氨基-4H-色烯的多组分合成及其生物活性

  摘要：

  描述了一种制备(2-氨基-3-氰基-4H-苯并-4-基)膦酸酯衍生物的新方法。五甲基二乙烯三胺（PMDTA）催化水杨醛、丙二腈和亚磷酸二烷基酯的多组分反应，以高产率提供双环衍生物。所开发的方法不需要色谱分离，因为可以通过简单的过滤从反应混合物中回收产物。我们的方法还可以与仲氧化膦缩合，并且该反应以前在文献中尚未报道过。通过单晶 XRD 分析研究了五种衍生物的晶体结构。还探讨了合成的(2-氨基-4H-铬-4-基)膦酸盐对不同细胞系的体外细胞毒性和抗菌活性。根据测定的 IC 50值，几种衍生物对小鼠成纤维细胞 (NIH/3T3) 和人早幼粒细胞白血病 (HL-60) 细胞表现出中等或有希望的活性。此外，三种(2-氨基-3-氰基-4H-铬-4-基)氧化膦对选定的革兰氏阳性菌具有活性。

  DOI：

  10.1039/d1ob01204e

文献信息

• 5-Hydroxypentylammonium acetate as a reusable ionic liquid catalyzes tandem Knoevenagel-phospha-Michael reaction of aldehydes, malononitrile and phosphites
  作者：S. Sobhani、M. Honarmand

  DOI：10.1007/s13738-012-0088-1

  日期：2012.10

  5-Hydroxypentylammonium acetate as a task-specific ionic liquid promotes efficient tandem Knoevenagel-phospha-Michael reaction of phosphite esters with aryl/heteroaryl/alkyl/salicylaldehydes and malonitrile/ethyl cyanoacetate at room temperature in short reaction times. This simple procedure allows a series of β-phosphonomalonates and 4-substituted 2-amino-4H-chromenes with phosphonic acid dialkyl esters to be synthesized in good to high yields in the presence of an ionic liquid for the first time.

  5-羟基戊基铵乙酸盐作为一种特定任务的离子液体，促进了在室温下快速反应的磷酸酯与芳基/杂芳基/烷基/水杨醛和丙二腈/乙基氰乙酸酯的高效串联Knoevenagel-磷法-迈克尔反应。这一简单的方法首次在离子液体存在下合成了一系列β-磷酸马隆酸酯和4-取代的2-氨基-4H-色烯，产率良好至高。
• Solvent- and Catalyst-free Synthesis of (2-Amino-3-cyano-4H-chromen-4-yl) Phosphonates
  作者：Gullapalli Kumaraswamy、Nimmakayala Raghu、Rangaraju Satish Kumar

  DOI：10.1080/00304948.2014.944403

  日期：2014.9.3

  protocol is a multicomponent reaction (MCR). A number of MCRs have been developed for the preparation of libraries of privileged structures.10–16 Amongst three-component syntheses, the generation of (2-amino-3-cyano-4H-chromen-4-yl) phosphonates is considered a prominent protocol owing to the incorporation of a phosphorus atom in the molecule.17,18 A number of reactions catalyzed by Brønsted base,19–21

  由于这些化合物的生物活性，具有多种复杂性的高度官能化小分子的合成受到了相当多的关注。1-9 虽然已经报道了几种方法，但最广泛使用的方案是多组分反应 (MCR)。许多 MCR 已被开发用于制备特权结构库。 10-16 在三组分合成中，(2-amino-3-cyano-4H-chromen-4-yl) 膦酸酯的生成被认为是一个突出的由于在分子中掺入了一个磷原子，因此该协议是由 Brønsted 碱、19-21 路易斯酸、22,23 碘、24 β-环糊精、25 或聚乙二醇 (PEG)、26 催化的许多反应。已报道用于合成 (2-amino-3-cyano-4H-chromen-4-yl) 膦酸酯。
• Multicomponent Synthesis of Potentially Biologically Active Heterocycles Containing a Phosphonate or a Phosphine Oxide Moiety
  作者：Nóra Popovics-Tóth、Erika Bálint

  DOI：10.17344/acsi.2022.7648

  日期：——

  Several multicomponent synthetic approaches were elaborated for plenty of novel nitrogen or oxygen heterocycles containing a phosphonate or a phosphine oxide moiety. All multicomponent reactions were optimized through a model reaction in respect of the heating mode, molar ratio of the starting materials, atmosphere, catalyst, temperature, reaction time and solvent applied, and then, the extended preparation of small libraries of structurally-related compounds was performed. Most of the reactions could be considered as “green syntheses”, as they were carried out in the absence of any catalyst and/or solvent using microwave (MW) irradiation or even at ambient temperature. The scaling-up of a MW-assisted synthesis was also elaborated in a continuous flow MW system. Altogether more than 150 heterocyclic organophosphorus compounds were synthesized, among them several derivatives showed moderate or promising activity against the HL-60 cell line and Bacillus subtilis bacteria.

  为了大量制备含有膦酸盐或氧化膦分子的新型氮杂环或氧杂环，我们精心设计了几种多组分合成方法。所有多组分反应都通过模型反应进行了优化，包括加热方式、起始原料的摩尔比、气氛、催化剂、温度、反应时间和所用溶剂等，然后扩展制备了结构相关的小化合物库。大多数反应可被视为 "绿色合成"，因为它们是在没有任何催化剂和/或溶剂的情况下，利用微波（MW）辐照甚至在环境温度下进行的。此外，还在连续流微波系统中阐述了如何扩大微波辅助合成的规模。总共合成了 150 多种杂环有机磷化合物，其中有几种衍生物对 HL-60 细胞系和枯草芽孢杆菌表现出中等或有希望的活性。
• Synthesis of 2-amino-3-cyano-4H-chromen-4-ylphosphonates and their anticancer properties
  作者：Reddi Mohan Naidu Kalla、Jin-Seok Choi、Jin-Wook Yoo、Seong Jin Byeon、Min Seon Heo、Il Kim

  DOI：10.1016/j.ejmech.2014.02.025

  日期：2014.4

  A series of 2-amino-3-cyano-4H-chromen-4-ylphosphonates have been synthesized by reacting substituted salicylaldehydes, malononitrile, and dialkylphosphites using a catalytic amount of dibutylamine as an organocatalyst employing Knoevenagel, Pinner, and phospha-Michael reactions simultaneously in ethanol. This protocol is an environmentally friendly procedure and gives high yields of the desired compounds (85-96%). In addition, no extraction or chromatography steps are needed to obtain the desired products. The compounds are tested against the viability of adenocarcinomic human alveolar basal epithelial (A549) and human epidermoid cancer (KB) cell lines using an MU assay. Among these, diethyl 2-amino-3-cyano-4H-chromen-4-ylphosphonate and diethyl 2-amino-6-bromo-3-cyano-4H-chromen-4-ylphosphonate showed promising anticancer activity against the two tested cell lines. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Silica-Bonded 2-Hydroxyethylammonium Acetate as an Efficient and Recyclable Catalyst for the Synthesis of 2-Amino-4H-chromen-4-yl Phosphonates and β-Phosphonomalonates
  作者：Sara Sobhani、Moones Honarmand

  DOI：10.1007/s10562-013-0968-8

  日期：2013.5

  Silica-bonded 2-hydroxyethylammonium acetate was synthesized easily by the reaction of 3-chloropropylsilica with ethanolamine followed by ion exchange with acetate. It was used as a heterogeneous, re-usable, efficient and easy to handle catalyst for the one-pot synthesis of a variety of 2-Amino-4H-chromen-4-yl phosphonates and beta-phosphonomalonates at room temperature under solvent-free conditions.