(+/-)-N-ethoxycarbonyldehydronorglaucine | 7630-72-0

• 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-ethoxycarbonyldehydronorglaucine
• 英文别名: (+/-)-N-carbethoxydehydronorglaucine；1,2,9,10-tetramethoxy-4,5-dihydro-dibenzo[de,g]quinoline-6-carboxylic acid ethyl ester；N-Ethoxycarbonyl-6a,7-dehydro-N-norglaucin；N-Carbethoxy-6a,7-dehydronorglaucin；N-Carbethoxydehydro-N-glaucin；Ethyl 1,2,9,10-tetramethoxy-4,5-dihydro-6H-dibenzo(de,g)quinoline-6-carboxylate；ethyl 4,5,15,16-tetramethoxy-10-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1,3,5,7,9(17),13,15-heptaene-10-carboxylate
• CAS: 7630-72-0
• 化学式: C₂₃H₂₅NO₆
• 分子量: 411.455
• InChiKey: UBNQMQAKEHACQS-UHFFFAOYSA-N

物化性质

• 沸点：
  581.4±50.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  66.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+/-)-N-ethoxycarbonyldehydronorglaucine 在 吡啶 、 氢氧化钾 作用下， 以 水 、 异丙醇 为溶剂， 反应 25.0h， 生成 2-(N-carbonyldehydronorgalucine)propanoic acid
  参考文献：
  名称：

  New N-Substituted (±)-Dehydronorglaucine Analogs

  摘要：

  The aporphine alkaloid N-carbethoxydehydronorglaucine (1) was found to have promising in vitro antitumor activity, but poor water solubility. We report the synthesis of 1, the efficient hydrolysis of its urethane group and the further transformation into several new dehydronorglaucine analogs.

  DOI：

  10.1080/00397919508015508
• 作为产物：
  描述：

  1-(6'=bromo-3',4'-dimethoxybenzylidene)-6,7-dimethoxy-3,4-dihydroisoquinoline N-ethylcarbamate 在 potassium tert-butylate 作用下， 以 正丁醇 、 苯 为溶剂， 反应 60.0h， 以55%的产率得到(+/-)-N-ethoxycarbonyldehydronorglaucine
  参考文献：
  名称：

  New N-Substituted (±)-Dehydronorglaucine Analogs

  摘要：

  The aporphine alkaloid N-carbethoxydehydronorglaucine (1) was found to have promising in vitro antitumor activity, but poor water solubility. We report the synthesis of 1, the efficient hydrolysis of its urethane group and the further transformation into several new dehydronorglaucine analogs.

  DOI：

  10.1080/00397919508015508

文献信息

• Gupta, Sandeep; Bhakuni, Dewan S., Synthetic Communications, 1989, vol. 19, # 3and4, p. 393 - 402
  作者：Gupta, Sandeep、Bhakuni, Dewan S.

  DOI：——

  日期：——
• Castedo, Luis; Iglesias, Teresa; Puga, Alberto, Heterocycles, 1981, vol. 15, # 2, p. 915 - 918
  作者：Castedo, Luis、Iglesias, Teresa、Puga, Alberto、Saa, Jose M.、Suau, Rafael

  DOI：——

  日期：——
• GUPTA, SANDEEP;BHAKUNI, DEWAN S., SYNTH. COMMUN., 19,(1989) N-4, C. 393-401
  作者：GUPTA, SANDEEP、BHAKUNI, DEWAN S.

  DOI：——

  日期：——
• New N-Substituted (±)-Dehydronorglaucine Analogs
  作者：Violeta Benedetti-Doctorovich、Fu-Yung Huang、John Lambropoulos、Edward M. Burgess、Leon H. Zalkow

  DOI：10.1080/00397919508015508

  日期：1995.11

  The aporphine alkaloid N-carbethoxydehydronorglaucine (1) was found to have promising in vitro antitumor activity, but poor water solubility. We report the synthesis of 1, the efficient hydrolysis of its urethane group and the further transformation into several new dehydronorglaucine analogs.