ethyl 2-amino-6,8-dichloro-4-(diethoxyphosphoryl)-4H-chromene-3-carboxylate | 1239859-60-9

• 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: ethyl 2-amino-6,8-dichloro-4-(diethoxyphosphoryl)-4H-chromene-3-carboxylate
• 英文别名: ethyl 2-amino-6,8-dichloro-4-diethoxyphosphoryl-4H-chromene-3-carboxylate
• CAS: 1239859-60-9
• 化学式: C₁₆H₂₀Cl₂NO₆P
• 分子量: 424.218
• InChiKey: GCRIKJCPZILXNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  97.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  亚磷酸二乙酯 、 氰乙酸乙酯 、 3,5-二氯水杨醛 在 choline chloride-urea 作用下， 反应 2.7h， 生成 ethyl 2-amino-6,8-dichloro-4-(diethoxyphosphoryl)-4H-chromene-3-carboxylate
  参考文献：
  名称：

  基于氯化胆碱的低共熔溶剂，在温和条件下通过多组分反应有效合成 2-氨基-4H-色烯-4-基膦酸酯衍生物

  摘要：

  摘要 水杨醛、丙二腈/氰基乙酸乙酯和亚磷酸二烷基酯在温和条件下，在可重复使用的低共熔溶剂 (DES) 存在下，通过一锅三组分反应合成了 2-氨基-4H-色烯-4-基膦酸酯衍生物. 该方法的优点是反应条件温和，后处理程序简单，使用 DES 作为绿色溶剂，是制备重要的生物活性含磷化合物的经济方案。图形概要

  DOI：

  10.1080/10426507.2017.1417296

文献信息

• Simple, Efficient, and Catalyst-Free Synthesis of (2-Amino-4H-1-benzopyran-4-yl)phosphonates in Polyethylene Glycol
  作者：Biswanath Das、Penagaluri Balasubramanyam、Gandolla Chinna Reddy、Nayaki Salvanna

  DOI：10.1002/hlca.201000461

  日期：2011.7

  Several (2‐amino‐4H‐1‐benzopyran‐4‐yl)phosphonates were efficiently synthesized by employing a multicomponent protocol involving a salicylaldehyde, malononitrile or ethyl cyanoacetate, and a trialkyl phosphite in polyethylene glycol. The latter could be recovered and re‐used. No additional solvent or catalyst was required. To the best of our knowledge, this is the first report of the one‐pot preparation

  通过使用涉及水杨醛，丙二腈或氰基乙酸乙酯的多组分方案以及聚乙二醇中的亚磷酸三烷基酯，可以有效地合成几种（2-氨基-4- H -1-苯并吡喃-4-基）膦酸酯。后者可以回收再利用。不需要额外的溶剂或催化剂。据我们所知，这是一次单罐制备（2-氨基-4 H -1-苯并吡喃-4-基）膦酸二甲酯的报告。
• Green Synthesis and Bioactivity of 2-Amino-4<i>H</i>-chromen-4-yl-phosphonates
  作者：Mekala Rajasekhar、Kunda Uma Maheswara Rao、Chereddy Syama Sundar、Nemallapudi Bakthavatchala Reddy、Sandip Kumar Nayak、Cirandur Suresh Reddy

  DOI：10.1248/cpb.c12-00160

  日期：——

  A simple and efficient one pot synthesis of 2-amino-4H-chromen-4-yl phosphonate derivatives has been accomplished by the condensation of salicylaldehyde, malononitrile/ethylcyanoacetate and triethyl phosphite/trimethyl phosphite in the presence of molecular iodine as catalyst in water at room temperature. All the reactions were very clean and the products were obtained in very good to excellent yields. The title compounds are characterized by IR, 1H-, 13C-, 31P-NMR and mass spectra, also studied their antimicrobial and antioxidant activity.

  通过在室温下在水中使用分子碘作为催化剂，采用水杨 aldehyde、丙二腈/乙基氰基乙酸酯和三乙基磷酸酯/三甲基磷酸酯的缩合反应，成功实现了一种简单高效的一锅法合成2-氨基-4H-香烯-4-基磷酸酯衍生物。所有反应均非常干净，产物的收率从非常好到优秀。标题化合物通过红外光谱、1H-、13C-、31P-NMR及质谱进行表征，并研究了其抗菌和抗氧化活性。
• One-pot synthesis of 2-amino-4H-chromen-4-yl phosphonate derivatives using β-cyclodextrin as reusable catalyst in water
  作者：S. Narayana Murthy、B. Madhav、V. Prakash Reddy、Y.V.D. Nageswar

  DOI：10.1016/j.tetlet.2010.05.028

  日期：2010.7

  Various 2-amino-4H-chromen-4-yl phosphonate derivatives were synthesized in good yields by condensation of salicylaldehyde, malononitrile or ethylcyanoacetate, and triethyl phosphite using beta-cyclodextrin as a reusable catalyst under neutral conditions, in water. (C) 2010 Elsevier Ltd. All rights reserved.