2-(1-Hydroxy-1-methylethyl)-4H-furo[3,2-c][1]benzopyran-4-one

• 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: 2-(1-Hydroxy-1-methylethyl)-4H-furo[3,2-c][1]benzopyran-4-one
• 英文别名: 2-(2-hydroxypropan-2-yl)-4H-furo[3,2-c]chromen-4-one；2-(2-Hydroxypropan-2-yl)furo[3,2-c]chromen-4-one
• 化学式: C₁₄H₁₂O₄
• 分子量: 244.247
• InChiKey: MVXNXKZJBBWZLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-(3-hydroxy-3-methylbut-1-ynyl) chromen-4-one 在 air 、 copper(l) chloride 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以55%的产率得到2-(1-Hydroxy-1-methylethyl)-4H-furo[3,2-c][1]benzopyran-4-one
  参考文献：
  名称：

  Two Efficient Cascade Reactions to Synthesize Substituted Furocoumarins

  摘要：

  We have developed two efficient one-pot reactions to generate furo[3,2-c]coumarins and chlorofuro[3,2-c]coumarins through addition/cyclization/oxidation and chlorination. One cascade addition/cyclization/oxidation sequence of 1 with H2O in the presence of 20% CuCl as Lewis acid under an air atmosphere generated the 2-substituted-4H-furo[3,2-c]chromen-4-one 2. Another sequence in the presence of 10% CuBr and excess CuCl2 as the oxidant afforded the 3-chloro2-substituted-4H-furo[3,2-c]chromen-4-one 3.

  DOI：

  10.1021/jo800439y

文献信息

• Synthesis of Furocoumarins via Rhodium(II)-Catalysed Heterocyclisation of 3-Diazobenzopyran-2,4-(3H)-dione with Terminal Alkynes
  作者：Stefano Tollari、Giovanni Palmisano、Sergio Cenini、Giancarlo Cravotto、Giovanni B. Giovenzana、Andrea Penoni

  DOI：10.1055/s-2001-12765

  日期：——

  The rhodium (II) acetate-catalysed decomposition of 3-diazobenzopyran-2,4(3H)-dione in the presence of a terminal alkyne gave rise to a mixture of isomeric 2-substituted furo[3,2-c]coumarin and furo[2,3-b]coumarin, resulting from a formal [3+2] cycloaddition.

  在末端炔存在下，乙酸铑 (II) 催化分解 3-重氮苯并吡喃-2,4(3H)-二酮，生成异构体 2-取代呋喃并[3,2-c]香豆素和呋喃的混合物[2,3-b]香豆素，由正式的[3+2]环加成反应产生。
• Two Efficient Cascade Reactions to Synthesize Substituted Furocoumarins
  作者：Gang Cheng、Youhong Hu

  DOI：10.1021/jo800439y

  日期：2008.6.1

  We have developed two efficient one-pot reactions to generate furo[3,2-c]coumarins and chlorofuro[3,2-c]coumarins through addition/cyclization/oxidation and chlorination. One cascade addition/cyclization/oxidation sequence of 1 with H2O in the presence of 20% CuCl as Lewis acid under an air atmosphere generated the 2-substituted-4H-furo[3,2-c]chromen-4-one 2. Another sequence in the presence of 10% CuBr and excess CuCl2 as the oxidant afforded the 3-chloro2-substituted-4H-furo[3,2-c]chromen-4-one 3.