3-(2-Bromo-ethyl)-5-hydroxy-7-pentyl-chromen-2-one | 137060-02-7

• 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: 3-(2-Bromo-ethyl)-5-hydroxy-7-pentyl-chromen-2-one
• 英文别名: 3-(2-Bromoethyl)-5-hydroxy-7-pentylchromen-2-one
• CAS: 137060-02-7
• 化学式: C₁₆H₁₉BrO₃
• 分子量: 339.229
• InChiKey: HITCWPNWWXPTGN-UHFFFAOYSA-N

物化性质

• 沸点：
  469.6±45.0 °C(Predicted)
• 密度：
  1.375±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-Bromo-ethyl)-5-hydroxy-7-pentyl-chromen-2-one 、 丙烯酸甲酯（MA） 在 2,6-二叔丁基-4-甲基苯酚 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以34%的产率得到1-hydroxy-10-(methoxycarbonyl)-3-pentyl-7,8,9,10-tetrahydrodibenzo-α-pyrone
  参考文献：
  名称：

  3-Vinylcoumarins and 3-vinylchromenes as dienes. Application to the synthesis of 3,4-fused coumarins and chromenes

  摘要：

  The reaction of alpha-(diethylphosphono)-gamma-butyrolactones 1 with o-hydroxyaryl aldehydes 2 and 7 gave 3-(2-hydroxyethyl)coumarins 3 in excellent yields. Treatment of 3 or 3-(2-hydroxyethyl)-2,2-dimethylchromenes 11 derived from 3 with triphenylphosphine dibromide led to the corresponding 3-(2-bromoethyl)coumarins 8 or 3-(2-bromoethyl)chromenes 12 in good yields. The Diels-Alder reaction of the 3-vinylcoumarins 13 or the 3-vinylchromenes 31, generated in situ from treatment of the bromides 8 or 12 with DBU, with a variety of dienophiles 14-19 and 35 produced regiospecific [2 + 4] cycloadducts, 3,4-fused coumarins 20-28 or 3,4-fused chromenes 32-34 and 36 in good to moderate yields.

  DOI：

  10.1021/jo00027a032
• 作为产物：
  描述：

  2-formyl-5-pentylresorcinol 1,3-bis-(methoxymethyl) ether 在 盐酸 、 sodium hydride 、 triphenylphosphine dibromide 1:1 addition complex 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 10.0h， 生成 3-(2-Bromo-ethyl)-5-hydroxy-7-pentyl-chromen-2-one
  参考文献：
  名称：

  3-Vinylcoumarins and 3-vinylchromenes as dienes. Application to the synthesis of 3,4-fused coumarins and chromenes

  摘要：

  The reaction of alpha-(diethylphosphono)-gamma-butyrolactones 1 with o-hydroxyaryl aldehydes 2 and 7 gave 3-(2-hydroxyethyl)coumarins 3 in excellent yields. Treatment of 3 or 3-(2-hydroxyethyl)-2,2-dimethylchromenes 11 derived from 3 with triphenylphosphine dibromide led to the corresponding 3-(2-bromoethyl)coumarins 8 or 3-(2-bromoethyl)chromenes 12 in good yields. The Diels-Alder reaction of the 3-vinylcoumarins 13 or the 3-vinylchromenes 31, generated in situ from treatment of the bromides 8 or 12 with DBU, with a variety of dienophiles 14-19 and 35 produced regiospecific [2 + 4] cycloadducts, 3,4-fused coumarins 20-28 or 3,4-fused chromenes 32-34 and 36 in good to moderate yields.

  DOI：

  10.1021/jo00027a032