2-(8,9,10-trimethoxy-1,2,3,4-tetrahydrophenanthridin-4-yl)ethanol | 199786-97-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(8,9,10-trimethoxy-1,2,3,4-tetrahydrophenanthridin-4-yl)ethanol
• CAS: 199786-97-5
• 化学式: C₁₈H₂₃NO₄
• 分子量: 317.385
• InChiKey: NWUJTGDNZJRHGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  60.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(8,9,10-trimethoxy-1,2,3,4-tetrahydrophenanthridin-4-yl)ethanol 在 三氯化磷 作用下， 以 苯 为溶剂， 反应 0.33h， 以87%的产率得到9,10,11-Trimethoxy-1,2,3,3a,4,5-hexahydro-pyrrolo[3,2,1-de]phenanthridinylium; chloride
  参考文献：
  名称：

  Total Synthesis of (±)-Roserine

  摘要：

  Electrophilic cyclization of amino ketals 14a and 14b with 6 M HCl at 23 degrees C, followed by oxidation with air in 6 M HCl at 100 degrees C, gave tetrahydrophenanthridines 16a and 16b, respectively, which were transformed into the pyrrolophenanthridinium salts 1a and 1b. Compound 1b was shown to be the correct structure of the Narcissus pallidulus constituent, roserine.

  DOI：

  10.1021/jo971641o
• 作为产物：
  描述：

  (8,9,10-trimethoxy-1,2,3,4-tetrahydrophenanthridin-4-yl)acetic acid 在 盐酸 、 乙醇 、 dimethyl sulfide borane 作用下， 生成 (8,9,10-Trimethoxy-1,2,3,4-tetrahydro-phenanthridin-4-yl)-acetic acid ethyl ester 、 2-(8,9,10-trimethoxy-1,2,3,4-tetrahydrophenanthridin-4-yl)ethanol
  参考文献：
  名称：

  Total Synthesis of (±)-Roserine

  摘要：

  Electrophilic cyclization of amino ketals 14a and 14b with 6 M HCl at 23 degrees C, followed by oxidation with air in 6 M HCl at 100 degrees C, gave tetrahydrophenanthridines 16a and 16b, respectively, which were transformed into the pyrrolophenanthridinium salts 1a and 1b. Compound 1b was shown to be the correct structure of the Narcissus pallidulus constituent, roserine.

  DOI：

  10.1021/jo971641o

文献信息

• Total Synthesis of (±)-Roserine
  作者：Aaron E. Bunnell、Lee A. Flippin、Yanzhou Liu

  DOI：10.1021/jo971641o

  日期：1997.12.1

  Electrophilic cyclization of amino ketals 14a and 14b with 6 M HCl at 23 degrees C, followed by oxidation with air in 6 M HCl at 100 degrees C, gave tetrahydrophenanthridines 16a and 16b, respectively, which were transformed into the pyrrolophenanthridinium salts 1a and 1b. Compound 1b was shown to be the correct structure of the Narcissus pallidulus constituent, roserine.