ethyl 2-amino-4-(diethylphosphoryl)-8-methoxy-4H-chromene-3-carboxylate | 1239859-63-2

• 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-4-(diethylphosphoryl)-8-methoxy-4H-chromene-3-carboxylate
• 英文别名: ethyl 2-amino-4-(diethoxyposphoryl)-8-methoxy-4H-chromen-3-carboxylate；ethyl 2-amino-4-(diethoxyphosphoryl)-8-methoxy-4H-chromene-3-carboxylate；ethyl 2-amino-4-[diethoxy(oxido)phosphaniumyl]-8-methoxy-4H-chromene-3-carboxylate
• CAS: 1239859-63-2
• 化学式: C₁₇H₂₄NO₇P
• 分子量: 385.354
• InChiKey: RNTRWRMHTRKECZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  邻香草醛 、 亚磷酸二乙酯 、 氰乙酸乙酯 在 choline chloride-urea 作用下， 反应 2.6h， 以89%的产率得到ethyl 2-amino-4-(diethylphosphoryl)-8-methoxy-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。
• Synthesis of 2-Amino-4H-Chromen-4-yl Phosphonats via C-P Bond Formation Catalyzed by Nano-Rods ZnO Under Solvent-Free Condition
  作者：Mona Hosseini-Sarvari、Atefeh Roosta

  DOI：10.2174/13862073113166660064

  日期：2014.1.31

  One-pot, three-component reactions of structurally diverse salicylaldehydes with malononitrile (or ethylcyanoacetate) and diethyl (or dimethyl) phosphate are carried out in the presence of nano-rods ZnO as an efficient catalyst for the synthesis of biologically interesting 2-amino-4H-chromen-4-yl phosphonate derivatives. The value of this method lies in its mild and environmentally benign reaction, simple procedure, good yields, and ease of handling.

  在纳米棒 ZnO 作为高效催化剂的存在下，将结构多样的水杨醛与丙二腈（或氰乙酸乙酯）和磷酸二乙酯（或磷酸二甲酯）进行一锅三组分反应，合成了具有生物学意义的 2-amino-4H-chromen-4-yl phosphonate 衍生物。该方法的价值在于其反应温和、对环境无害、程序简单、收率高且易于操作。
• One-Pot Synthesis of <font>β</font>-Phosphonomalonates Catalyzed by Molecular Iodine
  作者：Sara Sobhani、Roya Jahanshahi

  DOI：10.1080/00397911.2013.768670

  日期：2013.12.17

  A one-pot procedure has been developed for the synthesis of -phosphonomalonates via P-C bond formation through tandem Knoevenagel-phospha-Michael reaction catalyzed by iodine as a new, inexpensive, nonmetallic, and commercially available catalyst. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]
• 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.
• Choline chloride based eutectic solvent for the efficient synthesis of 2-amino-4<i>H</i>-chromen-4-yl phosphonate derivatives via multicomponent reaction under mild conditions
  作者：Suresh Kumar Krishnammagari、Byung Gwon Cho、Yeon Tae Jeong

  DOI：10.1080/10426507.2017.1417296

  日期：2018.5.4

  ABSTRACT Synthesis of 2-amino-4H-chromen-4-ylphosphonate derivatives has been accomplished by the one-pot three-component reaction of salicylaldehyde, malononitrile/ethylcyanoacetate and dialkyl phosphites in the presence of reusable deep eutectic solvent (DES) under mild conditions. The advantages of this method are mild reaction conditions, simple work-up procedure, use of DES as a green solvent

  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