10-(methoxycarbonyl)-1-(methoxymethoxy)-3-pentyl-7,8,9,10-tetrahydrobenzo-α-pyrone | 137059-93-9

• 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: 10-(methoxycarbonyl)-1-(methoxymethoxy)-3-pentyl-7,8,9,10-tetrahydrobenzo-α-pyrone
• 英文别名: Methyl 1-(methoxymethoxy)-6-oxo-3-pentyl-7,8,9,10-tetrahydrobenzo[c]chromene-10-carboxylate
• CAS: 137059-93-9
• 化学式: C₂₂H₂₈O₆
• 分子量: 388.461
• InChiKey: DREABEMWVOSXOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-(2-bromoethyl)-5-(methoxymethoxy)-7-pentylcoumarin 、 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 7.5h， 以67%的产率得到10-(methoxycarbonyl)-1-(methoxymethoxy)-3-pentyl-7,8,9,10-tetrahydrobenzo-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

文献信息

• 3-Vinylcoumarins and 3-vinylchromenes as dienes. Application to the synthesis of 3,4-fused coumarins and chromenes
  作者：Toru Minami、Yasuyuki Matsumoto、Seigo Nakamura、Shinichiro Koyanagi、Masahiko Yamaguchi

  DOI：10.1021/jo00027a032

  日期：1992.1

  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.