ethyl 8,13-dioxo-8,13-dihydro-benzo[5,6]indolo[2,1-a]isoquinoline-14-carboxylate | 114864-23-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: ethyl 8,13-dioxo-8,13-dihydro-benzo[5,6]indolo[2,1-a]isoquinoline-14-carboxylate
• 英文别名: 8,13-dihydro-14-ethoxycarbonylbenz[5,6]indolo[2,1-a]isoquinoline-8,13-dione；14-ethoxycarbonylbenz[5,6]indolo[2,1-a]isoquinoline-8,13-dione；8,13-dioxo-8,13-dihydro-benz[5,6]indolo[2,1-a]isoquinoline-14-carboxylic acid ethyl ester；8,13-Dioxo-8,13-dihydro-benz[5,6]indolo[2,1-a]isochinolin-14-carbonsaeure-aethylester；Ethyl 8,13-dioxo-8,13-dihydrobenz[5,6]indolo[2,1-a]isoquinoline-14-carboxylate；ethyl 3,10-dioxo-1-azapentacyclo[11.8.0.02,11.04,9.014,19]henicosa-2(11),4,6,8,12,14,16,18,20-nonaene-12-carboxylate
• CAS: 114864-23-2
• 化学式: C₂₃H₁₅NO₄
• 分子量: 369.376
• InChiKey: MEKVPIXQCWHQOP-UHFFFAOYSA-N

物化性质

• 熔点：
  240-241 °C(Solvent: Ligroine; Chloroform)
• 沸点：
  60-90 °C
• 密度：
  1.37±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  64.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 8,13-dioxo-8,13-dihydro-benzo[5,6]indolo[2,1-a]isoquinoline-14-carboxylate 、 sodium ethanolate 在 乙醇 作用下， 生成 benz<5,6>indole<1,2-a>isoquinoline-8,13-dione
  参考文献：
  名称：

  Reactions of Naphthoquinones with Malonic Ester and its Analogs. III. 1-Substituted Phthaloyl- and Phthaloylbenzopyrrocolines¹

  摘要：

  DOI：

  10.1021/ja01562a048
• 作为产物：
  描述：

  N-(2-苯基乙基)-甲酰胺 在 PPA 、 乙醇 、 钯 作用下， 生成 ethyl 8,13-dioxo-8,13-dihydro-benzo[5,6]indolo[2,1-a]isoquinoline-14-carboxylate
  参考文献：
  名称：

  Reactions of Naphthoquinones with Malonic Ester and its Analogs. III. 1-Substituted Phthaloyl- and Phthaloylbenzopyrrocolines¹

  摘要：

  DOI：

  10.1021/ja01562a048

文献信息

• Copper(II)-Catalyzed Carbon–Carbon Triple Bond Cleavage of Internal Alkynes for the Synthesis of Annulated Indolizines
  作者：Jinwei Sun、Fuyao Wang、Huayou Hu、Xiangshan Wang、Hui Wu、Yun Liu

  DOI：10.1021/jo500456d

  日期：2014.5.2

  Cleavage of C≡C bond in butynedioates via copper(II)-catalyzed reaction has been achieved, leading to the synthesis of benzo[f]pyrido[1,2-a]indole-6,11-diones in high yields by one-pot three-component reactions. In this unprecedented C≡C bond cleavage reaction of internal alkynes, both fragments from the alkyne are successively incorporated into the products.

  通过铜（II）催化的反应实现了对丁炔中C≡C键的裂解，从而导致高收率的苯并[ f ]吡啶并[1,2- a ]吲哚-6,11-二酮的单-合成。锅三成分反应。在内部炔烃的这种前所未有的C≡C键裂解反应中，来自炔烃的两个片段均先后结合到产物中。
• Copper(II)-Catalyzed Synthesis of Benzo[<i>f</i>]pyrido[1,2-<i>a</i>]indole-6,11-dione Derivatives via Naphthoquinone Difunctionalization Reaction
  作者：Yun Liu、Jin-Wei Sun

  DOI：10.1021/jo2023312

  日期：2012.1.20

  and pyridine (or isoquinoline) via sp2–C–H difunctionalization of naphthoquinone followed by intramolecular cyclization and oxidative aromatization. In an attempt to expand the reaction scope and to help clarify the reaction mechanism, 1,3-dicarbonyl compounds are used in place of acyl bromides to take part in this reaction, and the benzo[f]pyrido[1,2-a]indole-6,11-diones derivatives are also obtained

  苯并[ f ]吡啶基[1,2 - a ]吲哚-6,11-二酮通过铜（II）催化的酰基溴，1,4-萘醌和吡啶的三组分反应（或异喹啉）通过萘醌的sp 2 -CH双官能化，然后进行分子内环化和氧化芳构化。为了扩大反应范围并澄清反应机理，使用1,3-二羰基化合物代替酰基溴参与了该反应，并使用了苯并[ f ]吡啶基[1,2- a ]还以优异的产率获得了吲哚-6，11-二酮衍生物。
• Synthesis of polycyclic indolizine derivatives via one-pot tandem reactions of N-ylides with dichloro substituted α,β-unsaturated carbonyl compounds
  作者：Yun Liu、Hua-You Hu、Qing-Jian Liu、Hong-Wen Hu、Jian-Hua Xu

  DOI：10.1016/j.tet.2006.12.050

  日期：2007.2

  Convenient and regioselective syntheses of 1,2-annulated, and 1,2-, 5,6- and 1,2-, 7,8-bisannulated polycyclic indolizine derivatives have been achieved by one-pot tandem reactions of cyclic N-ylides derived from the corresponding N-substituted pyridinium, quinolinium, and isoquinolinium salts 1–3 with dichloro substituted α,β-unsaturated carbonyl compounds 4–7. The reactions of the N-ylides with 2

  通过一锅串联的衍生自环状N酰基的串联反应可以方便地和区域选择性地合成1,2-环和1,2-，5,6-和1,2-，7,8-双环的多吲哚嗪衍生物从相应的ñ取代的吡啶鎓，喹啉鎓，和异喹啉盐1 - 3与二氯取代的α，β不饱和羰基的化合物4 - 7。所述的反应Ñ -ylides与2,3- dichloroindenone 4，3,4- dichlorocoumarin 5，和4a，6,7,8a四氯-1,4- methanonaphthalene -5,8-二酮6依次进行[3 + 2]环加成反应，并从环加合物中除去氯化氢。另一方面，N-酰基化物与2,3-二氯-1,4-萘醌7的反应是通过新的反应顺序进行的，得到的产物为15 – 17。
• Microwave-Assisted Multicomponent Synthesis of Aza-, Diaza-, Benzo-, and Dibenzofluorenedione Derivatives
  作者：Andrea Defant、Graziano Guella、Ines Mancini

  DOI：10.1080/00397910802044249

  日期：2008.8.18

  Abstract A microwave procedure was efficiently applied to the synthesis of a series of heteropolycyclic compounds with known or potential biological activities. Antitumor amide 3was obtained in a few minutes and with high yields through a solventless, one-pot cyclization, followed by treatment with the suitable amine. This method was also used to access tetracyclic aza-compounds 5/6, where their selective

  摘要 微波方法有效地应用于合成一系列具有已知或潜在生物活性的杂多环化合物。通过无溶剂的一锅环化，然后用合适的胺处理，在几分钟内以高收率获得了抗肿瘤酰胺 3。该方法还用于获得四环氮杂化合物 5/6，其中在无溶剂条件下或通过改变溶剂，在固体存在下研究它们作为 N,N-syn 和 N,N-反区域异构体的选择性形成载体和催化量的环保金属盐。在这种情况下，通过微波辐射改进了使用预制吡啶鎓或异喹啉鎓叶立德在常规加热下对类似多环化合物的热访问，并扩展到二氮杂酯的合成。在任何情况下，一锅三组分环化比 N-ylide 序列的原子效率更高。
• Mathur; Tilak, Journal Of Scientific and Industrial Research, 1958, vol. 17 B, p. 33,38
  作者：Mathur、Tilak

  DOI：——

  日期：——