euxylophoricine C | 38990-11-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: euxylophoricine C
• 英文别名: Euxylophoricin C；18,20-Dioxa-3,13,24-triazahexacyclo[11.11.0.02,10.04,9.015,23.017,21]tetracosa-1(24),2(10),4,6,8,15,17(21),22-octaen-14-one；18,20-dioxa-3,13,24-triazahexacyclo[11.11.0.02,10.04,9.015,23.017,21]tetracosa-1(24),2(10),4,6,8,15,17(21),22-octaen-14-one
• CAS: 38990-11-3
• 化学式: C₁₉H₁₃N₃O₃
• 分子量: 331.331
• InChiKey: ROYNNIHWGRMUAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-<2-(3-indolyl)ethyl>-6,7-(methylenedioxy)-2-(trifluoromethyl)-4(3H)-quinazolinone 在 盐酸 、 氢氧化钾 、 溶剂黄146 作用下， 以 二甲基亚砜 为溶剂， 反应 0.83h， 生成 euxylophoricine C
  参考文献：
  名称：

  Studies of rutaecarpine and related quinazolinocarboline alkaloids

  摘要：

  DOI：

  10.1021/jo00208a018

文献信息

• Condensation of anthranilic acids with pyridines to furnish pyridoquinazolones via pyridine dearomatization
  作者：Yajun Yang、Cuiju Zhu、Min Zhang、Shijun Huang、Jingjing Lin、Xiandao Pan、Weiping Su

  DOI：10.1039/c6cc07365d

  日期：——

  The unprecedented carbodiimide-mediated condensation between pyridines and anthranilic acids via pyridines dearomatization at room temperature has been developed to provide a straightforward approach to pyridoquinazolones. The value of this approach...

  已经开发出前所未有的碳二亚胺介导的吡啶与邻氨基苯甲酸之间在室温下经由吡啶脱芳香化作用的缩合反应，从而为吡啶基喹唑酮提供了直接的方法。这种方法的价值...
• Total Synthesis of Rutaecarpine and Analogues by Tandem Azido Reductive Cyclization Assisted by Microwave Irradiation
  作者：Ahmed Kamal、Nagula Shankaraiah、M. Reddy、T. Reddy、Leonardo Santos

  DOI：10.1055/s-0030-1259095

  日期：2011.1

  The total synthesis ofrutaecarpine and several analogues has been developed by using an azido reductive cyclization process starting from substituted azido benzoic acids. The intramolecular azido reductive cyclization step was performed with triphenylphosphine or Ni 2 B in HCl―MeOH (1 M) using microwave irradiation. This synthetic route is amenable for the generation of a library of quinazolinone compounds

  已经通过使用从取代的叠氮基苯甲酸开始的叠氮基还原环化过程开发了芸香果芸香碱和几种类似物的全合成。分子内叠氮基还原环化步骤使用三苯基膦或 Ni 2 B 在 HCl-MeOH (1 M) 中使用微波辐射进行。该合成路线适用于生成喹唑啉酮化合物库。
• One-pot reductive-cyclization as key step for the synthesis of rutaecarpine alkaloids
  作者：Chih-Shone Lee、Cheng-Kuo Liu、Yuen-Lin Chiang、Yen-Yao Cheng

  DOI：10.1016/j.tetlet.2007.11.094

  日期：2008.1

  The quinazolinocarboline alkaloids including rutaecarpine (1a), euxylophoricine A (1b), and euxylophoricine C (1c) have been synthesized efficiently from the ring opened β-carboline derivative as key intermediate by a one-pot reductive-cyclization reaction. The key intermediate was prepared from tryptamine (6) following Bischler–Napieralski cyclization, benzoylation, and oxidative cleavage of the exocyclic

  通过一锅还原环化反应，以开环β-咔啉衍生物为主要中间体，有效地合成了芸苔芸香碱（1a），硫氧鸟嘌呤A（1b）和硫氧鸟嘌呤C（1c）等喹唑啉基咔啉生物碱。在Bischler–Napieralski环化，苯甲酰化和环外双键的氧化裂解后，由色胺（6）制备关键中间体。
• A New and Facile Synthesis of Rutaecarpine Alkaloids
  作者：Chih-Shone Lee、Cheng-Kuo Liu、Yen-Yao Cheng、Che-Ming Teng

  DOI：10.3987/com-08-11606

  日期：——

  efficiently from the ring opened β-carboline derivatives (3a-d) as key intermediates. A unique one-pot reductive-cyclization as key reaction furnished the synthesis of rutaecarpine alkaloids in excellent yields. The key intermediates (3a-d) were prepared from tryptamine following acylation, Bischler-Napieralski cyclization, benzoylation, and oxidative cleavage of the exocyclic double bond. This new synthetic

  相关的rutaecarpine类似物（la-d）已从开环β-咔啉衍生物（3a-d）作为关键中间体有效合成。独特的一锅还原环化反应作为关键反应以优异的收率合成了芸香碱生物碱。关键中间体 (3a-d) 由色胺在酰化、Bischler-Napieralski 环化、苯甲酰化和环外双键的氧化裂解后制备。这种新的合成方法提供了一种容易获得对血小板聚集具有有效抑制作用的芸香芸香碱类似物。
• Kametani,T.; Fukumoto,K., Heterocycles, 1977, vol. 7, p. 615 - 635
  作者：Kametani,T.、Fukumoto,K.

  DOI：——

  日期：——