7-bromo-8-hydroxy-3-methylisochroman-1-one | 1266675-00-6

• 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: 7-bromo-8-hydroxy-3-methylisochroman-1-one
• 英文别名: 7-Bromo-8-hydroxy-3-methyl-3,4-dihydroisochromen-1-one
• CAS: 1266675-00-6
• 化学式: C₁₀H₉BrO₃
• 分子量: 257.084
• InChiKey: AOECDKZQCGPPBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  ethyl 5-hydroxy-2-hexynoate 、 4-bromo-3-hydroxy-2-pyrone 在 sodium hydride 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.33h， 以49%的产率得到7-bromo-8-hydroxy-3-methylisochroman-1-one
  参考文献：
  名称：

  The second generation synthesis of (+)-pseudodeflectusin

  摘要：

  The second generation synthesis of (+)-pseudodeflectusin (1), a potential antitumor agent, has been achieved. The key synthetic step is the cascade reaction involving Diels-Alder reaction, lactonization, and decarboxylation to give cycloadduct 6 with complete regioselectivity in good yield. We found that NaH is the best base to facilitate the Diels-Alder reaction of hydroxypyrone 7 with alkyne 8. The present synthetic route enables the total synthesis of (+)-1 in only five-steps from the known compounds 7 and 8. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.153