diethyl 2-amino-8-methyl-3-cyano-4H-chromen-4-ylphosphonate | 1351992-39-6

• 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: diethyl 2-amino-8-methyl-3-cyano-4H-chromen-4-ylphosphonate
• 英文别名: diethyl 2-amino-3-cyano-8-methyl-4H-chromen-4-ylphosphonate；2-amino-4-[diethoxy(oxido)phosphaniumyl]-8-methyl-4H-chromene-3-carbonitrile
• CAS: 1351992-39-6
• 化学式: C₁₅H₁₉N₂O₄P
• 分子量: 322.301
• InChiKey: RNNHOWFIQPWINH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-羟基-3-甲基苯甲醛 、 亚磷酸二乙酯 、 丙二腈 在 二乙胺 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以90%的产率得到diethyl 2-amino-8-methyl-3-cyano-4H-chromen-4-ylphosphonate
  参考文献：
  名称：

  使用二乙胺作为新型有机催化剂多组分合成 β-膦酰基丙二腈和 2-amino-4H-chromen-4-yl 膦酸酯的实用且高效的方案

  摘要：

  摘要 二乙胺在室温下通过醛、丙二腈和亚磷酸二烷基酯的三组分缩合反应，首次被证明是一种高效的有机催化剂，可用于无溶剂合成 β-膦酰基丙二腈。还描述了相同催化剂在二乙基（2-氨基-3-氰基-色烯-4-基）膦酸酯的合成中的适用性。

  DOI：

  10.1016/j.crci.2012.07.001

文献信息

• Synthesis of 2-amino-3-cyano-4H-chromen-4-ylphosphonates and 2-amino-4H-chromenes catalyzed by tetramethylguanidine
  作者：Reddi Mohan Naidu Kalla、Seong Jin Byeon、Min Seon Heo、Il Kim

  DOI：10.1016/j.tet.2013.10.052

  日期：2013.12

  Synthesis of 2-amino-4H-chromen-4-ylphosphonates and 2-amino-4H-chromenes has been accomplished by the reaction of salicylaldehyde, malononitrile, dialkyl/diphenylphosphites catalyzed by 1,1,3,3-tetramethylguanidine (TMG) under neat conditions at room temperature. The applicability of catalytic TMG for the synthesis of 2-amino-4H-chromenes also has been described. The mild reaction conditions, simple work-up procedure, and use of TMG as an inexpensive catalyst provides an economical protocol for the preparation of important phosphorus-containing compounds. (C) 2013 Elsevier Ltd. All rights reserved.
• Efficient one-pot synthesis of β-phosphono malonates and 2-amino-4H-chromen-4-ylphosphonate derivatives by ethylenediamine diacetate-catalyzed three-component reactions
  作者：Srinivasa Rao Kolla、Yong Rok Lee

  DOI：10.1016/j.tet.2011.10.060

  日期：2012.1

  One-pot three-component reactions of arylaldehyde or salicylaldehyde with malononitrile (or ethyl-cyanoacetate) and triethyl phosphite are carried out in the presence of ethylenediamine diacetate (EDDA) as a catalyst for the synthesis of biologically interesting beta-phosphono malonates and 2-amino-4H-chromen-4-ylphosphonate derivatives. The value of this method lies in its mild reaction catalyst and conditions, good yields, and ease of handling. (C) 2011 Elsevier Ltd. All rights reserved.
• A practical and highly efficient protocol for multicomponent synthesis of β-phosphonomalononitriles and 2-amino-4H-chromen-4-yl phosphonates using diethylamine as a novel organocatalyst
  作者：M.A. Kulkarni、V.R. Pandurangi、U.V. Desai、P.P. Wadgaonkar

  DOI：10.1016/j.crci.2012.07.001

  日期：2012.9

  has been demonstrated for the first time to be a highly efficient organocatalyst in the solvent-free synthesis of β-phosphonomalononitriles by a three component condensation of aldehyde, malononitrile and dialkyl phosphite at ambient temperature. The applicability of the same catalyst in the synthesis of diethyl (2-amino-3-cyano-chromene-4-yl) phosphonic acid esters has also been described.

  摘要 二乙胺在室温下通过醛、丙二腈和亚磷酸二烷基酯的三组分缩合反应，首次被证明是一种高效的有机催化剂，可用于无溶剂合成 β-膦酰基丙二腈。还描述了相同催化剂在二乙基（2-氨基-3-氰基-色烯-4-基）膦酸酯的合成中的适用性。