kalbretorine | 98899-99-1

• 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: kalbretorine
• 英文别名: 9-Hydroxy-5,7-dioxa-12-azapentacyclo[10.6.1.02,10.04,8.015,19]nonadeca-1(18),2,4(8),9,13,15(19),16-heptaen-11-one
• CAS: 98899-99-1
• 化学式: C₁₆H₉NO₄
• 分子量: 279.252
• InChiKey: REOYKJPVLPBVGR-UHFFFAOYSA-N

物化性质

• 沸点：
  461.3±45.0 °C(Predicted)
• 密度：
  1.68±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  60.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 kalbretorine 以 甲醇 、 乙醚 为溶剂， 反应 24.0h， 以4 mg的产率得到7-O-methylkalbretorine
  参考文献：
  名称：

  红花生物碱

  摘要：

  摘要 Haemanthus kalbreyeri 的根中含有一种新的菲啶酮生物碱kalbretorine 和一种新的葡萄糖氧基生物碱kalbreclasine。此外，六种已知的生物碱，即。以前从其他石蒜科植物中报道的haemanthamine、haemanthidine、hippadine、lycorine、narciclasine 和pratorimine 现在也从该物种中分离出来。Kalbretorine 显着抑制 S-180 肿瘤细胞的生长和活力。Kalbreclasine 引起脾淋巴细胞的显着促有丝分裂激活，这是免疫刺激剂的特征。

  DOI：

  10.1016/s0031-9422(00)82560-1
• 作为产物：
  描述：

  去氢石蒜碱酮 在 硼酸三甲酯 、 双氧水 、 叔丁基锂 、 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 反应 40.0h， 生成 kalbretorine
  参考文献：
  名称：

  A Synthesis of Pyrrolophenanthridone Alkaloids via Consecutive Directed Lithiation and Palladium-catalyzed Cross-coupling Reactions

  摘要：

  A short and convergent synthesis of pyrrolophenanthridone alkaloids, such as anhydrolycorin-7-one, oxoassoanine, hippadine, and pratosine, was developed by using directed lithiation and palladium-catalyzed cross-coupling as key reactions. Anhydrolycorin-7-one was converted to an antitumor alkaloid, kalbretorine, via directed lithiation and hydroxylation reactions.

  DOI：

  10.3987/com-94-6777

文献信息

• Electrochemical Total Synthesis of Pyrrolophenanthridone Alkaloids: Controlling the Anodically Initiated Electron Transfer Process
  作者：Kazuhiro Okamoto、Kazuhiro Chiba

  DOI：10.1021/acs.orglett.0c01082

  日期：2020.5.1

  and dehydrogenative indole synthesis were developed. Both reactions were initiated by anodic oxidation of the same electron-rich indoline moiety, but the product selectivity was controlled by different electron-transfer processes. Intramolecular cross-coupling was achieved by the generation of a strong electrophilic radical cation intermediate in the MeNO2-HFIP-LiClO4 system. Indole formation was accomplished

  电化学分子内C（sp2）-H交叉偶联和脱氢吲哚合成的发展。两个反应均通过相同的富电子二氢吲哚部分的阳极氧化来引发，但产物的选择性受不同的电子转移过程控制。分子内交叉偶联是通过在MeNO2-HFIP-LiClO4系统中生成强亲电自由基阳离子中间体实现的。吲哚的形成是通过苄基氧化和连续去质子化完成的。我们将这些反应应用于天然吡咯并菲蒽酮生物碱的全合成。
• Synthesis of pyrrolophenanthridone alkaloid kalbretorine from indolecarboxylic acids via hypervalent iodine(III) mediated halodecarboxylation and reduction
  作者：Yasuyoshi Miki、Hideaki Umemoto、Masashi Dohshita、Hiromi Hamamoto

  DOI：10.1016/j.tetlet.2012.01.132

  日期：2012.4

  The treatment of 8,9,10-trimethoxy-7H-pyrrolo[3,2,1-de]phenanthridine-4,5-dicarboxylic acid with phenyliodine diacetate and potassium iodide in tetrahydrofuran gave the corresponding 4,5-diiodo derivative, which was converted to kalbretorine via reduction, demethylation, followed by alkylation. (C) 2012 Elsevier Ltd. All rights reserved.
• A Synthesis of Pyrrolophenanthridone Alkaloids via Consecutive Directed Lithiation and Palladium-catalyzed Cross-coupling Reactions
  作者：Masatomo Iwao、Hirokazu Takehara、Shigeru Obata、Mitsuaki Watanabe

  DOI：10.3987/com-94-6777

  日期：——

  A short and convergent synthesis of pyrrolophenanthridone alkaloids, such as anhydrolycorin-7-one, oxoassoanine, hippadine, and pratosine, was developed by using directed lithiation and palladium-catalyzed cross-coupling as key reactions. Anhydrolycorin-7-one was converted to an antitumor alkaloid, kalbretorine, via directed lithiation and hydroxylation reactions.
• Alkaloids of Haemanthus kalbreyeri
  作者：Shibnath Ghosal、Rajiv Lochan、Ashutosh Yatendra Kumar、Radhey S. Srivastava

  DOI：10.1016/s0031-9422(00)82560-1

  日期：1985.1

  Abstract The roots of Haemanthus kalbreyeri contain a new phenanthridone alkaloid, kalbretorine, and a new glucosyloxy alkaloid, kalbreclasine. Additionally, six known alkaloids, viz. haemanthamine, haemanthidine, hippadine, lycorine, narciclasine and pratorimine, previously reported from other Amaryllidaceous plants have now been isolated also from this species. Kalbretorine produced marked inhibition

  摘要 Haemanthus kalbreyeri 的根中含有一种新的菲啶酮生物碱kalbretorine 和一种新的葡萄糖氧基生物碱kalbreclasine。此外，六种已知的生物碱，即。以前从其他石蒜科植物中报道的haemanthamine、haemanthidine、hippadine、lycorine、narciclasine 和pratorimine 现在也从该物种中分离出来。Kalbretorine 显着抑制 S-180 肿瘤细胞的生长和活力。Kalbreclasine 引起脾淋巴细胞的显着促有丝分裂激活，这是免疫刺激剂的特征。