(Z)-N-(2-(3-isopropoxy-4-methoxystyryl)-4-isopropoxy-(5-methoxyphenyl)ethyl)-N-hydroxyprop-2-en-1-amine | 1507361-22-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (Z)-N-(2-(3-isopropoxy-4-methoxystyryl)-4-isopropoxy-(5-methoxyphenyl)ethyl)-N-hydroxyprop-2-en-1-amine
• 英文别名: N-[2-[5-methoxy-2-[(Z)-2-(4-methoxy-3-propan-2-yloxyphenyl)ethenyl]-4-propan-2-yloxyphenyl]ethyl]-N-prop-2-enylhydroxylamine
• CAS: 1507361-22-9
• 化学式: C₂₇H₃₇NO₅
• 分子量: 455.594
• InChiKey: DNTONAMIPVCFPP-LUAWRHEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (Z)-N-(2-(3-isopropoxy-4-methoxystyryl)-4-isopropoxy-(5-methoxyphenyl)ethyl)-N-hydroxyprop-2-en-1-amine 在 水 作用下， 以 苯 为溶剂， 反应 16.0h， 以45%的产率得到1-(3-isopropoxy-4-methoxybenzyl)-1,2,3,4-tetrahydro-7-isopropoxy-6-methoxyisoquinoline-N-(2-allyloxide)
  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：

  4-异丙氧基-3-甲氧基苯甲醛 在 copper(l) iodide 、 trans-bis(triphenylphosphine)palladium dichloride 、 氢气 、 溴 、 sodium cyanoborohydride 、 potassium carbonate 、 溶剂黄146 、 三乙胺 、 tin(ll) chloride 作用下， 以 甲醇 、 乙酸乙酯 、 乙腈 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 反应 46.0h， 生成 (Z)-N-(2-(3-isopropoxy-4-methoxystyryl)-4-isopropoxy-(5-methoxyphenyl)ethyl)-N-hydroxyprop-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