1-(3-isopropoxy-4-methoxybenzyl)-1,2,3,4-tetrahydro-7-isopropoxy-6-methoxyisoquinoline-N-(2-methylallyloxide) | 1108621-39-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 1-(3-isopropoxy-4-methoxybenzyl)-1,2,3,4-tetrahydro-7-isopropoxy-6-methoxyisoquinoline-N-(2-methylallyloxide)
• CAS: 1108621-39-1
• 化学式: C₂₈H₃₉NO₅
• 分子量: 469.621
• InChiKey: HJZHPMRLVNHDSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.93
• 重原子数：
  34.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.39
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-(3-isopropoxy-4-methoxybenzyl)-1,2,3,4-tetrahydro-7-isopropoxy-6-methoxyisoquinoline-N-(2-methylallyloxide) 在 三氯化硼 、 溶剂黄146 、 锌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 1-[(5-羟基-4-甲氧基-1-环己-2-烯基)甲基]-6-甲氧基-7-异喹啉醇
  参考文献：
  名称：

  Studies on Difficult Intramolecular Hydroaminations in the Context of Four Syntheses of Alkaloid Natural Products

  摘要：

  Examples of intramolecular alkene hydroaminations forming six-membered ring systems are rare, especially for systems in which the double bond is disubstituted. Such cyclizations have important synthetic relevance. Herein we report a systematic study of these cyclizations using recently developed Cope-type hydroamination methodologies. Difficult intramolecular alkene hydroaminations were used as key steps in syntheses of 2-epi-pumiliotoxin C, coniine, N-norreticuline and desbromoarborescidine A. This effort required the development of optimized hydroamination conditions to improve the efficiency of the cyclizations. Collectively, our results show that Cope-type cyclizations can be achieved on a variety of challenging substrates and proceed under similar conditions for both N-H and N-substituted hydroxylamines.

  DOI：

  10.1021/jo4023149
• 作为产物：
  描述：

  2-(2-(3-isopropoxy-4-methoxystyryl)-4-isopropoxy-5-methoxyphenyl)ethoxime 在 水 、 sodium cyanoborohydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 3.0h， 生成 1-(3-isopropoxy-4-methoxybenzyl)-1,2,3,4-tetrahydro-7-isopropoxy-6-methoxyisoquinoline-N-(2-methylallyloxide) 、 (E)-2-[2-(3-isopropoxy-4-methoxystyryl)-4-isopropoxy-5-methoxyphenyl]-N-hydroxy-2-methylprop-2-en-1-amine
  参考文献：
  名称：

  Studies on Difficult Intramolecular Hydroaminations in the Context of Four Syntheses of Alkaloid Natural Products

  摘要：

  Examples of intramolecular alkene hydroaminations forming six-membered ring systems are rare, especially for systems in which the double bond is disubstituted. Such cyclizations have important synthetic relevance. Herein we report a systematic study of these cyclizations using recently developed Cope-type hydroamination methodologies. Difficult intramolecular alkene hydroaminations were used as key steps in syntheses of 2-epi-pumiliotoxin C, coniine, N-norreticuline and desbromoarborescidine A. This effort required the development of optimized hydroamination conditions to improve the efficiency of the cyclizations. Collectively, our results show that Cope-type cyclizations can be achieved on a variety of challenging substrates and proceed under similar conditions for both N-H and N-substituted hydroxylamines.

  DOI：

  10.1021/jo4023149

文献信息

• Bourgeois, Joffre; Dion, Isabelle; Cebrowski, Pamela H., Journal of the American Chemical Society, 2009, vol. 131, p. 874 - 875
  作者：Bourgeois, Joffre、Dion, Isabelle、Cebrowski, Pamela H.、Loiseau, Francis、Bedard, Anne-Catherine、Beauchemin, Andre M.

  DOI：——

  日期：——