Ethyl 6-bromo-2-iminochromene-3-carboxylate | 891091-20-6

• 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: Ethyl 6-bromo-2-iminochromene-3-carboxylate
• CAS: 891091-20-6
• 化学式: C₁₂H₁₀BrNO₃
• 分子量: 296.12
• InChiKey: XXPYMWSCXFGKJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl 6-bromo-2-iminochromene-3-carboxylate 在 溶剂黄146 、 锌 作用下， 以 水 为溶剂， 反应 3.0h， 生成 ethyl 2-amino-4-((4-amino-3-methylisoxazol-5-yl)methyl)-6-bromo-4H-chromene-3-carboxylate
  参考文献：
  名称：

  Synthesis of 4 H ‐chromene‐isoxazole hybrids via ortho ‐hydroxy directing cyclization of isoxazole‐styrenes and Michael addition of imino‐chromenes in aqueous medium

  摘要：

  AbstractA green, efficient, and one‐pot method synthesis of functionalized 4H‐chromene‐isoxazole hybrids is reported via o‐hydroxy group directing cyclization of isoxazole‐styrenes and Michael addition of 3,5‐dimethyl‐4‐nitroisoxazole on 2‐imino‐2H‐chromene‐3‐carbonitrile (independent methods). The developed methodology was further extended for nitromethane, malononitrile, and alkylcyanoacetates as Michael donors.

  DOI：

  10.1002/jhet.4251
• 作为产物：
  描述：

  ethyl (E)-3-[5-bromo-2-(1-ethoxyethoxy)phenyl]-2-cyanoprop-2-enoate 在 Amberlyst 15 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 Ethyl 6-bromo-2-iminochromene-3-carboxylate 、 ethyl (E)-3-(5-bromo-2-hydroxyphenyl)-2-cyanoprop-2-enoate
  参考文献：
  名称：

  The synthesis of new, selected analogues of the pro-apoptotic and anticancer molecule HA 14-1

  摘要：

  A new and versatile strategy has been developed towards HA 14-1 analogues, selectively modified on position 4 and/or on the primary amine function. An important aspect was the appropriate selection of the phenol protective group in the 5-bromosalicylaldehyde, allowing the isolation of the key intermediate the 2H-benzopyrane-2-imine 2'. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.03.070

文献信息

• Visible Light‐Induced Metal‐free Arylation of Coumarin‐3‐carboxylates with Arylboronic Acids
  作者：Swarnayu Banik、Aita Saikiran、Prathyusha Permula、K. S. Srivishnu、B. Sridhar、B. V. Subba Reddy

  DOI：10.1002/asia.202400042

  日期：2024.4.16

  The present work represents a novel methodology for the selective arylation of coumarin‐3‐carboxylates with arylboronic acids via a photochemical route, marking the first‐ever attempt for the direct alkenyl C−H arylation using rose bengal as a photocatalyst, which is a readily available and cost‐effective alternative to transition metal catalysis. The reaction proceeds smoothly in MeOH/H2O solvent media in the presence of radical initiator affording the arylated products in good yields (60–80 %). The reaction parameters such as visible light, radical initiator, oxidant, anhydrous solvent, and inert atmosphere play a crucial role for the success of this methodology. The substituents present on the substrate show a significant effect on the conversion. This study provides a valuable contribution to the field of organic synthesis offering a new and efficient approach to the arylation of coumarin‐3‐carboxylic acid esters with a broad substrate scope and high functional group tolerance. It is a versatile method and provides a direct access to biologically relevant 4‐arylcoumarin‐3‐carboxylates.