(+/-)-N-ethoxycarbonylnorthaliporphine | 51015-10-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 阿朴菲
• 英文名称: (+/-)-N-ethoxycarbonylnorthaliporphine
• 英文别名: N-ethoxycarbonylwilsonirine；1-hydroxy-2,9,10-trimethoxy-4,5,6a,7-tetrahydro-dibenzo[de,g]quinoline-6-carboxylic acid ethyl ester；ethyl 1-hydroxy-2,9,10-trimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-6-carboxylate
• CAS: 51015-10-2
• 化学式: C₂₂H₂₅NO₆
• 分子量: 399.444
• InChiKey: UQLYUZFCMXYWRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  77.46
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (+/-)-N-ethoxycarbonylnorthaliporphine 在 lead(IV) acetate 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 12.83h， 生成 (4R,6aR)-2,9,10-Trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-1,4-diol
  参考文献：
  名称：

  Ogasawara, Hiromichi; Suzuki, Masaji; Shiohara, Tomohiro, Heterocycles, 1998, vol. 47, # 2, p. 911 - 919

  摘要：

  DOI：
• 作为产物：
  描述：

  (+/-)-7-benzyloxy-6-methoxy-1-(3,4-dimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline 在 palladium on activated charcoal 氢气 、 potassium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 4.55h， 生成 (+/-)-N-ethoxycarbonylnorthaliporphine
  参考文献：
  名称：

  Formation and Reaction of o-Quinol Acetates of N-Acyl- and N-Methanesulfonyl-1,2,3,4-tetrahydro-6-methoxyisoquinolin-7-ols

  摘要：

  Oxidation of N-formyl-, N-acetyl-, N-ethoxycarbonyl-, and N-methanesulfonyl-1,2,3,4-tetrahydro-6-methoxyisoquinolin-7-ols (1b-e) with lead tetraacetate in dichloromethane (CH2Cl2) produced quantitatively corresponding o-quinol acetates (2b-e), treatment of which with trifluoroacetic acid in CH2Cl2 at 0 degrees C for a few minutes afforded corresponding N-acyl- and N-methanesulfonyl-wilsonirines (4b-e) and N-acyl- and N-methanesulfonylnorsebiferines (5b-e). When the reaction was carried out at room temperature, o-quinol acetates (2d,e) of N-ethoxycarbonyl and N-methanesulfonyl congeners (Id,e) gave 1-[2(ethoxycarbonylamino)ethyl]- and 1-[2-(methanesulfonylamino)ethyl]-4-hydroxy-3,6,7-trimethoxyphenanthrenes (8d,e).

  DOI：

  10.3987/com-99-s84

文献信息

• Gupta, Sandeep; Bhakuni, Dewan S., Synthetic Communications, 1988, vol. 18, # 18, p. 2251 - 2258
  作者：Gupta, Sandeep、Bhakuni, Dewan S.

  DOI：——

  日期：——
• Formation and Reaction of o-Quinol Acetates of N-Acyl- and N-Methanesulfonyl-1,2,3,4-tetrahydro-6-methoxyisoquinolin-7-ols
  作者：Osamu Hoshino、Masaji Suzuki、Hiromichi Ogasawara

  DOI：10.3987/com-99-s84

  日期：——

  Oxidation of N-formyl-, N-acetyl-, N-ethoxycarbonyl-, and N-methanesulfonyl-1,2,3,4-tetrahydro-6-methoxyisoquinolin-7-ols (1b-e) with lead tetraacetate in dichloromethane (CH2Cl2) produced quantitatively corresponding o-quinol acetates (2b-e), treatment of which with trifluoroacetic acid in CH2Cl2 at 0 degrees C for a few minutes afforded corresponding N-acyl- and N-methanesulfonyl-wilsonirines (4b-e) and N-acyl- and N-methanesulfonylnorsebiferines (5b-e). When the reaction was carried out at room temperature, o-quinol acetates (2d,e) of N-ethoxycarbonyl and N-methanesulfonyl congeners (Id,e) gave 1-[2(ethoxycarbonylamino)ethyl]- and 1-[2-(methanesulfonylamino)ethyl]-4-hydroxy-3,6,7-trimethoxyphenanthrenes (8d,e).
• Ogasawara, Hiromichi; Suzuki, Masaji; Shiohara, Tomohiro, Heterocycles, 1998, vol. 47, # 2, p. 911 - 919
  作者：Ogasawara, Hiromichi、Suzuki, Masaji、Shiohara, Tomohiro、Hoshino, Osamu

  DOI：——

  日期：——