6,7-dihydro-6,8,13a-triaza-benzo[3,4]cyclohepta[1,2-b]naphthalene-5,13-dione | 65641-84-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 嘧啶二氮卓类
• 英文名称: 6,7-dihydro-6,8,13a-triaza-benzo[3,4]cyclohepta[1,2-b]naphthalene-5,13-dione
• 英文别名: 6,7-dihydro-7-methylquinazolino[3,2-a][1,4]benzodiazepine-5,13-dione；6,7-dihydrobenzo[6,7][1,4]diazepino[2,1-b]quinazoline-5,13-dione；6,7,7-trihydro-quinazolino[3,2-a][1,4]benzodiazepine-5,13-dione；6,7-dihydroquinazolino[3,2-a][1,4]-benzodiazepine-5,13-dione；6,7-dihydroquinazolino[3,2-a][1,4]benzodiazepine-5,13-dione；sclerotigenin
• CAS: 65641-84-1
• 化学式: C₁₆H₁₁N₃O₂
• 分子量: 277.282
• InChiKey: NGYKOTTXJAPLPC-UHFFFAOYSA-N

物化性质

• 熔点：
  235-238 °C
• 密度：
  1.45±0.1 g/cm3(Predicted)
• 溶解度：
  DMF：可溶； DMSO：可溶；乙醇：可溶；甲醇：可溶

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  61.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,7-dihydro-6,8,13a-triaza-benzo[3,4]cyclohepta[1,2-b]naphthalene-5,13-dione 、 三乙基氧翁四氟硼酸 以53%的产率得到
  参考文献：
  名称：

  HARRISON D. R.; KENNEWELL P. D.; TAYLOR J. B., J, HETEROCYCL. CHEM. , 1977, 14, NO 7, 1191-1196

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-二氢-1H-苯并[e][1,4]二氮杂卓-2,5-二酮 在 4-二甲氨基吡啶 、 三丁基膦 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 、 苯 为溶剂， 反应 4.0h， 生成 6,7-dihydro-6,8,13a-triaza-benzo[3,4]cyclohepta[1,2-b]naphthalene-5,13-dione
  参考文献：
  名称：

  Synthesis of circumdatin F and sclerotigenin. Use of the 2-nitrobenzyl group for protection of a diketopiperazine amide; synthesis of ent -fumiquinazoline G

  摘要：

  The Eguchi aza Wittig protocol has been used for the synthesis of sclerotigenin and circumdatin F by selective acylation of the more acidic anilide nitrogen of a benzodiazepinedione without the need for protecting groups. The use of the 2-nitrobenzyl group as a photochemically labile protecting group for the amide nitrogen of a diketopiperazine permits the use of the aza Wittig procedure for the synthesis of fumiquinazoline G. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00208-3

文献信息

• Synthesis of pyrazolopyrimidinones as sildenafil derivatives and sclerotigenin
  作者：Hoon Gu Heo、Jin Yu、Raveendra Jillella、Chang Ho Oh

  DOI：10.1080/00397911.2018.1459720

  日期：2018.7.3

  ABSTRACT A series of novel pyrazolo pyrimidinone derivatives (3(a–d), 4(a–d), and 6(a–d)) was synthesized from various pyrazolo amides (2a–d) which are synthesized by the reaction between ethyl 5-amino-3-methyl-1-phenyl-1H-pyrazole-4-carboxylate (1) and various lithium amides. In addition, we also described the synthesis of sclerotigenin drug molecule which has quinazoline moiety from simple 2-nitro

  摘要 从各种吡唑酰胺（2a-d）合成了一系列新型吡唑并嘧啶酮衍生物（3（a-d）、4（a-d）和6（a-d）） 5-amino-3-methyl-1-phenyl-1H-pyrazole-4-carboxylate (1) 和各种氨基锂。此外，我们还描述了从简单的2-硝基苯甲酸以高产率合成具有喹唑啉部分的硬化素药物分子。图形概要
• A Concise Building Block Approachto a Diverse Multi-Arrayed Library of the Circumdatin Family ofNatural Products
  作者：Andrew Thomas、Alfred Grieder

  DOI：10.1055/s-2003-40870

  日期：2003.8

  Using a polymer-supported phosphine-mediated intramolecular aza-Wittig reaction in a key step of a reaction sequence a diverse library of benzodiazepine-quinazolinone alkaloids (Circumdatins) has been prepared using a novel modified Eguchi protocol. The multi-arrayed library generation strategy commenced from readily accessible benzodiazepinedione derivatives (and anthranilic acids) and all library members were purified by reverse phase preparative HPLC.

  使用聚合物支持的膦介导的分子内氮杂维蒂希反应，在反应序列的关键步骤中，采用一种新型改良的Eguchi协议制备了一系列多样化的苯二氮杂氮烷-喹唑啉酮生物碱（Circumdatins）。多元化库的生成策略从易于获取的苯二氮杂双酮衍生物（和氨基苯甲酸）开始，所有库成员均通过反相制备HPLC进行纯化。
• Efficient syntheses of 2,3-disubstituted natural quinazolinones via iridium catalysis
  作者：Jie Fang、Jianguang Zhou

  DOI：10.1039/c2ob07178a

  日期：——

  Natural products sclerotigenin, pegamine, deoxyvasicinone, mackinazolinone, and rutaecarpine were synthesized. Core quinazolinone structures were constructed via Ir catalysis.

  天然产物癸肟酮、佩加美宁、脱氧瓦西酮、麦克那佐啉酮和鲁塔卡平被合成。核心喹嗪啉酮结构通过铱催化构建。
• Oxygen analogues of the benzodiazepine alkaloids sclerotigenin and circumdatin F
  作者：F. Anette Witt、Jan Bergman

  DOI：10.1002/jhet.5570390218

  日期：2002.3

  A new type of fused oxazepinones 9a and 9b, which are analogues of sclerotigenin and circumdatin F, were obtained in a two step synthesis from 2-(2-amino-benzoylamino)-benzoic acid or the corresponding methyl ester. Secondly a new synthesis of circumdatin F arose from this work, where 2-(2-propionylamino-benzoylamino)-benzoic acid methyl ester was used as an intermediate.

  由2-（2-氨基-苯甲酰氨基）-苯甲酸或相应的甲酯分两步合成，获得了一种新的稠合的恶唑烷酮9a和9b，它们是硬化素和环丁素F的类似物。其次，这项工作引起了新的环丁他汀合成，其中2-（2-丙酰氨基-苯甲酰氨基）-苯甲酸甲酯被用作中间体。
• Total synthesis of asperlicin C, circumdatin F, demethylbenzomalvin A, demethoxycircumdatin H, sclerotigenin, and other fused quinazolinones
  作者：Ming-Chung Tseng、Huei-Yun Yang、Yen-Ho Chu

  DOI：10.1039/b910545j

  日期：——

  Using scandium triflate and microwaves, the direct double dehydrocyclization of anthranilate-containing tripeptides was achieved, affording the total syntheses of (i) quinazolino[3,2-a]benzodiazepinediones (1a–f), (ii) diazepino[2,1-b]quinazolinediones (2a–e), and (iii) pyrazino[2,1-b]quinazolinediones (3a–e) with good overall isolated yields (23–43%, 37–47% and 31–56%, respectively). Among the quinazolino[3,2-a]benzodiazepinediones synthesized, 1a (sclerotigenin), 1b (circumdatin F), and 1f (asperlicin C) are natural products.

  使用氟化铈和微波，成功实现了含有氨基苯甲酸的三肽的直接双脱氢环化，获得了以下化合物的整体合成：（i）喹唑啉[3,2-a]苯二氮杂杂环二酮（1a-f），（ii）二氮杂氟[2,1-b]喹唑啉二酮（2a-e），以及（iii）吡嗪[2,1-b]喹唑啉二酮（3a-e），它们的整体分离产率分别为23-43%，37-47%和31-56%。在合成的喹唑啉[3,2-a]苯二氮杂杂环二酮中，1a（紫锈碱）、1b（环夭碱F）和1f（曲霉素C）是天然产物。

表征谱图