7-(3-hydroxyprop-1-ynyl)-4-methyl-2H-chromen-2-one | 1600531-65-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7-(3-hydroxyprop-1-ynyl)-4-methyl-2H-chromen-2-one
• 英文别名: 7-(3-Hydroxyprop-1-ynyl)-4-methylchromen-2-one；7-(3-hydroxyprop-1-ynyl)-4-methylchromen-2-one
• CAS: 1600531-65-4
• 化学式: C₁₃H₁₀O₃
• 分子量: 214.221
• InChiKey: RCHPKFQOCOEMSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  间苯二酚 在 吡啶 、 双(三环己基膦)二氯化钯 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 1.92h， 生成 7-(3-hydroxyprop-1-ynyl)-4-methyl-2H-chromen-2-one
  参考文献：
  名称：

  A rapid approach for the copper, amine, and ligand-free Sonogashira coupling of 4-methyl-7-nonafluorobutylsulfonyloxy coumarins under microwave irradiation

  摘要：

  A rapid, efficient, and reliable access for the synthesis of an assortment of 4-methyl-7-allcyl/aryl/heteroaryl alkynyl coumarins has been developed by the copper, amine, and ligand-free Sonogashira cross-coupling reaction of 4-methyl-7-nonafluorobutylsulfonyloxy coumarin with various terminal alkynes under microwave irradiation. In the presence of a suitable catalyst, base, and solvent, the coupling reaction proceeded smoothly to give the diaryl alkynes in satisfactory to exceptional yields. Nonaflates coupled more efficiently than the corresponding triflates which yielded the detriflated product as well as the hydrolyzed product as competing side products along with the required product. The utilization of TBAF center dot 3H(2)O as a mild base as well as a solvating agent was the key for success of the reaction. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.02.094

文献信息

• A rapid approach for the copper, amine, and ligand-free Sonogashira coupling of 4-methyl-7-nonafluorobutylsulfonyloxy coumarins under microwave irradiation
  作者：M. Nibin Joy、Yadav D. Bodke、K.K. Abdul Khader、Ayyiliyath M. Sajith

  DOI：10.1016/j.tetlet.2014.02.094

  日期：2014.4

  A rapid, efficient, and reliable access for the synthesis of an assortment of 4-methyl-7-allcyl/aryl/heteroaryl alkynyl coumarins has been developed by the copper, amine, and ligand-free Sonogashira cross-coupling reaction of 4-methyl-7-nonafluorobutylsulfonyloxy coumarin with various terminal alkynes under microwave irradiation. In the presence of a suitable catalyst, base, and solvent, the coupling reaction proceeded smoothly to give the diaryl alkynes in satisfactory to exceptional yields. Nonaflates coupled more efficiently than the corresponding triflates which yielded the detriflated product as well as the hydrolyzed product as competing side products along with the required product. The utilization of TBAF center dot 3H(2)O as a mild base as well as a solvating agent was the key for success of the reaction. (C) 2014 Elsevier Ltd. All rights reserved.