7,8,13,13b-tetrahydro-5H-benzo[1,2]indolizino[8,7-b]indol-5-one | 65020-20-4

• 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: 7,8,13,13b-tetrahydro-5H-benzo[1,2]indolizino[8,7-b]indol-5-one
• 英文别名: 7,8,13,13b-tetrahydro-5H-benz[1,2]indolizino[8,7-b]-indol-5-one；5,6,11b,12-Tetrahydro-6a,12-diaza-indeno[1,2-a]fluoren-7-one；10,20-diazapentacyclo[11.7.0.02,10.03,8.014,19]icosa-1(13),3,5,7,14,16,18-heptaen-9-one
• CAS: 65020-20-4
• 化学式: C₁₈H₁₄N₂O
• 分子量: 274.322
• InChiKey: IYYMNCLQZDBJKO-UHFFFAOYSA-N

物化性质

• 熔点：
  221-223 °C
• 沸点：
  510.8±50.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  36.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  7,8,13,13b-tetrahydro-5H-benzo[1,2]indolizino[8,7-b]indol-5-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以51%的产率得到tetrahydrobenzo[1,2]indolizino[8,7-b]indole
  参考文献：
  名称：

  Dopamine/Serotonin Receptor Ligands. 10: SAR Studies on Azecine-type Dopamine Receptor Ligands by Functional Screening at Human Cloned D₁, D_2L, and D₅ Receptors with a Microplate Reader Based Calcium Assay Lead to a Novel Potent D₁/D₅ Selective Antagonist

  摘要：

  On the basis of the benz[d]indolo[2,3-g]azecine derivative I (LE300), structure-activity relations were investigated in order to identify the pharmacophore in this new class of ligands. Various structural modifications were performed and the inhibitory activities at human cloned D-1, D-2L, and D-5 receptors were measured by using a simple fluorescence microplate reader based calcium assay. Subsequently, the affinities of active compounds were estimated by radioligand binding experiments. Deleting one of the aromatic rings as well as replacing it by a phenyl moiety abolishes the inhibitory activities almost completely. Contraction of the 10-membered central ring decreases them significantly. The replacement of indole by thiophene or N-methylpyrrole reduces the inhibitory activity, whereas replacing the indole by benzene increases it. Finally, the hydroxylated dibenz[d,g]azecine derivative 11d (LE404) was found to be more active than the lead I in the functional calcium assay as well as in radioligand displacement experiments.

  DOI：

  10.1021/jm050846j
• 作为产物：
  描述：

  2,3-二氢-3-羟基-2-[2-(1H-吲哚-3-基)乙基]-1H-异吲哚-1-酮 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 7,8,13,13b-tetrahydro-5H-benzo[1,2]indolizino[8,7-b]indol-5-one
  参考文献：
  名称：

  Metal ion-catalysed reduction of indolic imides, a facile β-carboline synthesis

  摘要：

  DOI：

  10.1016/s0040-4039(00)77834-8

文献信息

• Propylphosphonic anhydride (T3P®) mediated synthesis of 3-oxoisoindoline-1-carboxamides from 2-formylbenzoic acid, amines, and isocyanides. Preparation of isoindolinone alkaloids
  作者：Valentina Varga、Mátyás Milen、Péter Ábrányi-Balogh

  DOI：10.1016/j.tetlet.2018.08.063

  日期：2018.10

  Propylphosphonic anhydride (T3P®) was successfully applied to the synthesis of an isoindolinone library by the utilization of an Ugi four-center, three-component reaction (Ugi-4C-3CR). The use of T3P® significantly shortened the required reaction time and the corresponding products were obtained in good to high yields. Moreover, a side-reaction was observed when phenylethylamine derivatives and tryptamine

  通过利用Ugi四中心三组分反应（Ugi-4C-3CR），丙基膦酸酐（T3P®）成功应用于异吲哚啉酮文库的合成。T3P®的使用大大缩短了所需的反应时间，并以高至高收率获得了相应的产物。此外，当使用苯乙胺衍生物和色胺作为胺组分时，观察到副反应。将后者反应用于微波辅助的一锅法合成异喹啉生物碱（±）-新胺。出乎意料的是，在存在T3P®的情况下，传统的Ugi四组分反应（Ugi-4CR）无法成功。在这种情况下，从多组分反应中产生了除羧酸之外的α-氨基酰胺。
• Racemic and diastereoselective construction of indole alkaloids under solvent- and catalyst-free microwave-assisted Pictet–Spengler condensation
  作者：Mouhamad Jida、Olivier-Mohamad Soueidan、Benoit Deprez、Guillaume Laconde、Rebecca Deprez-Poulain

  DOI：10.1039/c2gc16596a

  日期：——

  An environment-friendly high-yielding method for the racemic and asymmetric diastereoselective preparation of indole alkaloids via Pictet–Spengler reaction is reported. The reaction proceeds with short reaction times under solvent-free and microwave-irradiation conditions.

  报道了一种环境友好且高产率的吲哚生物碱制备方法，通过Pictet-Spengler反应实现外消旋和不对称对映选择性合成。该反应在无溶剂和微波辐射条件下进行，反应时间短。
• Diverse privileged <i>N</i>-polycyclic skeletons accessed from a metal-free cascade cyclization reaction
  作者：Wenzhong Li、Yu Wang、Huijing Qi、Ran Shi、Jiazhu Li、Si Chen、Xin-Ming Xu、Wei-Li Wang

  DOI：10.1039/d1ob01206a

  日期：——

  An exquisite metal-free cascade cyclization reaction of 2-acylbenzoic acids with amines was developed, which provided a powerful method for the one-pot synthesis of diverse isoindoloisoquinoline and benzoindolizinoindole derivatives. This protocol avoided the use of metal catalysts, proceeded with high efficiency and had broad substrate scope. These resulting products could be transformed into tertiary

  开发了一种精致的2-酰基苯甲酸与胺的无金属级联环化反应，为多种异吲哚异喹啉和苯并吲嗪吲哚衍生物的一锅法合成提供了强有力的方法。该方案避免了金属催化剂的使用，效率高，底物范围广。这些所得产物可以在LiAlH 4 /AlCl 3还原下转化为叔胺，然后进行霍夫曼消除，以优异的产率提供大量含氮九元环化合物。所有含有稠合N-多环骨架的合成产物均难以用传统方法构建，在医药领域具有广泛的应用。
• Nouvelle voie d'accés en une étape au squelette de la benzo [g] indole [2,3a] indolizinone-5: Etude structurale en RMN 2D
  作者：M. Laguerre、C. Boyer、M. Atfani

  DOI：10.1016/s0040-4020(01)86079-8

  日期：1988.1

  A one pot synthesis of benzo [g] indolo [2,3-a] indolizinone-5 is described. Starting from tryptamine hydrochloride and methyl o-phthalaldehydic acid ester, 85% yield is obtained in refluxing n-butanol. In spite of differences with published data, the structure of final compound has been firmly established by 2D heteronuclear correlation NMR spectroscopy.

  描述了一锅合成苯并[g]吲哚[2，3-a]吲哚嗪酮-5。从盐酸色胺胺和邻苯二甲酸邻苯二甲酸甲酯开始，在回流的正丁醇中获得85％的收率。尽管与已公开的数据存在差异，但最终化合物的结构已通过2D异核相关NMR光谱法牢固建立。
• Synthesis of isoindolo[1,2-a]isoquinoline and isoindolo[2,1-a]quinoline derivatives via trifluoroacetic acid-mediated cascade reactions
  作者：Zhuo Huang、Yonggang Meng、Yangang Wu、Chuanjun Song、Junbiao Chang

  DOI：10.1016/j.tet.2021.132280

  日期：2021.7

  Condensation of methyl 2-acylbenzoates with 2-arylethanamines or 2-acylanilines in the presence of trifluoroacetic acid resulted in the formation of isoindolo[1,2-a]isoquinolines or isoindolo[2,1-a]quinolines, respectively, in moderate to excellent isolated yields.

  甲基2-acylbenzoates与2- arylethanamines或在三氟乙酸的存在下2- acylanilines的缩合导致形成异吲哚基的[1,2一]异喹啉或异吲哚基[2,1-一个〕喹啉，分别在中度至优良的分离产率。