(+/-)-dehydronorglaucine | 39945-38-5

• 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: (+/-)-dehydronorglaucine
• 英文别名: 4,5,15,16-Tetramethoxy-10-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1,3,5,7,9(17),13,15-heptaene
• CAS: 39945-38-5
• 化学式: C₂₀H₂₁NO₄
• 分子量: 339.391
• InChiKey: SHTFFTQYBKDUNJ-UHFFFAOYSA-N

物化性质

• 沸点：
  554.1±50.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  49
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+/-)-dehydronorglaucine 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 16.25h， 生成 N-(2-(N-piperazine)carbethoxy)-dehydronorglaucine
  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：

  N-(trifluoroacetyl)dehydronorglaucine 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.17h， 以85%的产率得到(+/-)-dehydronorglaucine
  参考文献：
  名称：

  The intermolecular benzyne cycloaddition approach to dehydronoraporprines and oxoaporphines. Total synthesis of PO-3

  摘要：

  DOI：

  10.1016/s0040-4039(00)88958-3

文献信息

• Aryl Radical Cyclizations of 1-(2‘-Bromobenzyl)isoquinolines with AIBN−Bu₃SnH:  Formation of Aporphines and Indolo[2,1-<i>a</i>]isoquinolines
  作者：Kazuhiko Orito、Shiho Uchiito、Yoshitaka Satoh、Takashi Tatsuzawa、Rika Harada、Masao Tokuda

  DOI：10.1021/ol990360v

  日期：2000.2.1

  text] Radical cyclization of alkoxy-substituted 1-(2'-bromobenzyl)-3,4-dihydroisoquinolines 1 with AIBN-Bu3SnH gave 6a,7-dehydroaporphines 2 preferentially. A steric repulsion between the respective alkoxy groups at the 7- and 3'-positions gave 5,6-dihydroindolo[2,1-a]isoquinolines 3 in a "disfavored" 5-endo cyclization mode. Radical cyclizations of the related substrates, such as 1-(2'-bromobenzoyl)isoquinolines

  [反应：见正文]用AIBN-Bu3SnH对烷氧基取代的1-（2'-溴苄基）-3,4-二氢异喹啉1进行自由基环化，优先得到6a，7-脱氢紫杉醇2。在7-和3'-位的各个烷氧基之间的空间排斥以“不利的” 5-内-环化模式得到5，6-二氢吲哚并[2，1-a]异喹啉3。还发现相关底物如1-（2'-溴苯甲酰基）异喹啉或1-（2'-溴-α-羟基苄基）异喹啉的自由基环化产生相应的氧杂卟啉或羟磷灰石。
• Intermolecular benzyne cycloaddition (IBC) approach to aporphinoids. Total syntheses of norcepharadione B, cepharadione B, dehydroanonaine, duguenaine, dehydronornuciferine, pontevedrine, O-methylatheroline, lysicamine, and alkaloid PO-3
  作者：N. Atanes、L. Castedo、E. Guitian、C. Saa、J. M. Saa、R. Suau

  DOI：10.1021/jo00009a010

  日期：1991.4

  We describe a useful novel approach to the synthesis of aporphinoids, including dehydroaporphines, aristolactams, 4,5-dioxoaporphines, and 7-oxoaporphines, by means of intermolecular benzyne cycloaddition (IBC). Specifically, we report the total synthesis of the isoquinoline alkaloids norcepharadione B, cepharadione B, dehydroanonaine, duguenaine, dehydronornuciferine, pontevedrine, O-methylatheroline, lysicamine, and alkaloid PO-3.
• 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：——
• Castedo, Luis; Saa, Jose M.; Suau, Rafael, Heterocycles, 1980, vol. 14, # 8, p. 1131 - 1134
  作者：Castedo, Luis、Saa, Jose M.、Suau, Rafael、Villaverde, Carmen

  DOI：——

  日期：——