methyl 6-(but-3-yn-1-yl)-7-hydroxy-8-methoxy-1-oxo-1H-isochromene-3-carboxylate | 1431956-48-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异香豆素及其衍生物
• 英文名称: methyl 6-(but-3-yn-1-yl)-7-hydroxy-8-methoxy-1-oxo-1H-isochromene-3-carboxylate
• 英文别名: Methyl 6-but-3-ynyl-7-hydroxy-8-methoxy-1-oxoisochromene-3-carboxylate；methyl 6-but-3-ynyl-7-hydroxy-8-methoxy-1-oxoisochromene-3-carboxylate
• CAS: 1431956-48-7
• 化学式: C₁₆H₁₄O₆
• 分子量: 302.284
• InChiKey: JODLBZGJEHVFOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 6-(but-3-yn-1-yl)-7-hydroxy-8-methoxy-1-oxo-1H-isochromene-3-carboxylate 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 silica gel supported sodium hydrogen sulfate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 17.0h， 生成 methyl 4,7,10'-trimethoxy-5,8,9'-trioxo-4',5,8,9'-tetrahydro-3H,3'H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[4,3-g]chromene]-7'-carboxylate
  参考文献：
  名称：

  Total Synthesis of (±)-δ-Rubromycin

  摘要：

  Transition-metal-catalyzed spiroketalization cyclization has been performed successfully and has led to the first total synthesis of (+/-)-delta-rubromycin with a longest linear sequence of 18 steps from commercially available guaiacol in a 2.7% overall yield.

  DOI：

  10.1021/ol400864f
• 作为产物：
  描述：

  在 silica gel supported sodium hydrogen sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以97%的产率得到methyl 6-(but-3-yn-1-yl)-7-hydroxy-8-methoxy-1-oxo-1H-isochromene-3-carboxylate
  参考文献：
  名称：

  Total Synthesis of (±)-δ-Rubromycin

  摘要：

  Transition-metal-catalyzed spiroketalization cyclization has been performed successfully and has led to the first total synthesis of (+/-)-delta-rubromycin with a longest linear sequence of 18 steps from commercially available guaiacol in a 2.7% overall yield.

  DOI：

  10.1021/ol400864f

文献信息

• Total Synthesis of (±)-δ-Rubromycin
  作者：Wenjing Wang、Jijun Xue、Tian Tian、Jie Zhang、Liping Wei、Jidong Shao、Zhixiang Xie、Ying Li

  DOI：10.1021/ol400864f

  日期：2013.5.17

  Transition-metal-catalyzed spiroketalization cyclization has been performed successfully and has led to the first total synthesis of (+/-)-delta-rubromycin with a longest linear sequence of 18 steps from commercially available guaiacol in a 2.7% overall yield.