1-(dicyanomethylene)-8-methyl-2,3,4,9-tetrahydro-1H-carbazole | 1293289-18-5

• 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: 1-(dicyanomethylene)-8-methyl-2,3,4,9-tetrahydro-1H-carbazole
• 英文别名: 1-(dicyanomethylene)-8-methyl-2,3,4,9-tetrahydrocarbazole
• CAS: 1293289-18-5
• 化学式: C₁₆H₁₃N₃
• 分子量: 247.299
• InChiKey: NQCHGCQJXDUAPZ-UHFFFAOYSA-N

物化性质

• 沸点：
  484.2±40.0 °C(Predicted)
• 密度：
  1.277±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  19.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  63.37
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(dicyanomethylene)-8-methyl-2,3,4,9-tetrahydro-1H-carbazole 在 sulfur 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以23%的产率得到2-amino-9-methyl-10H-thieno[3,2-a]carbazol-1-carbonitrile
  参考文献：
  名称：

  脯氨酸催化高效合成官能化噻吩并咔唑

  摘要：

  一种新的合成路线已被开发用于通过高度取代thienocarbazoles的合成升-脯氨酸介导gewald反应。该方法具有清洁反应，简单方法，高收率，容易纯化和催化剂的经济可用性的优点。

  DOI：

  10.1002/jhet.2784
• 作为产物：
  描述：

  8-甲基-2,3,4,9-1H-咔唑-1-酮 、 丙二腈 在 ammonium acetate 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以74%的产率得到1-(dicyanomethylene)-8-methyl-2,3,4,9-tetrahydro-1H-carbazole
  参考文献：
  名称：

  脯氨酸催化高效合成官能化噻吩并咔唑

  摘要：

  一种新的合成路线已被开发用于通过高度取代thienocarbazoles的合成升-脯氨酸介导gewald反应。该方法具有清洁反应，简单方法，高收率，容易纯化和催化剂的经济可用性的优点。

  DOI：

  10.1002/jhet.2784

文献信息

• A new strategy for the synthesis of diverse benzo[<i>a</i>]carbazoles <i>via</i> a divergent catalytic Michael reaction
  作者：Arya Kripalaya Ratheesh、Hazel A. Sparkes、Karnam Jayarampillai Rajendra Prasad

  DOI：10.1039/c8ob00154e

  日期：——

  4-benzo[a]carbazole] hybrids via amine-controlled divergent reactions. The spiro products were also obtained in good yields. The structures of the synthesized cycloadducts were confirmed by elemental analysis, spectral data (FT-IR, 1H, 13C NMR and HRMS) and by single-crystal X-ray diffraction studies.The application of this divergent tandem Michael addition protocol is beneficial from the viewpoint of the diversity-oriented

  α，α-二氰基亚甲基咔唑与β-硝基苯乙烯的新型发散串联迈克尔加成反应可提供高收率的多功能苯并[ a ]咔唑[BCs]和苯并二氢[ a ]咔唑[BDHCs]。此外，通过胺控制的发散反应，α，α-二氰基亚甲基咔唑，烯醌和丙二腈的直接多组分转化导致未报告的亚氨基和氨基官能化的螺[ac-8-8,4-苯并[ a ]咔唑]杂化物的形成。还获得了高产率的螺环产物。合成的环加合物的结构通过元素分析，光谱数据（FT-IR，1 H，13C NMR和HRMS）以及通过单晶X射线衍射研究。从简单的起始原料以多样性为导向一锅合成苯并[ a ]咔唑衍生物的观点，这种发散的串联迈克尔加成方案的应用是有益的。
• Regioselective cycloaddition of acetylenic esters: a one-pot synthesis of novel dihydrobenzo[a]carbazoles
  作者：Ezhumalai Yamuna、Matthias Zeller、Karnam Jayarampillai Rajendra Prasad

  DOI：10.1016/j.tetlet.2011.01.125

  日期：2011.4

  A one-pot procedure for the synthesis of highly substituted dihydrobenzo[a]carbazole derivatives via a regioselective cyclocondensation reaction between 2-(2,3,4,9-tetrahydro-carbazol-1-ylidene)-propanedinitrile and acetylenic esters is described.

  描述了一种通过一锅法通过2-（2,3,4,9-四氢咔唑-1-亚甲基）-丙腈和炔属酯之间的区域选择性环缩合反应合成高度取代的二氢苯并[ a ]咔唑衍生物的方法。
• Convenient framework of poly functionalized (E)-2-benzylideno-(Z)-carbazolylideno cyanoacetamides via rearrangements as an efficient antibiofilm inhibitors with SAR study
  作者：Perumal Sathiyachandran、Jabastin Jayamanoharan、Vladimir N. Nesterov、Karnam Jayarampillai Rajendra Prasad

  DOI：10.1016/j.bmc.2019.01.015

  日期：2019.3

  A simple and one-pot approach for the synthesis of highly functionalized novel (E)-2-benzylideno-(Z)-carbazolylideno cyanoacetamide derivatives from different 2-(2',3',4',9'-tetrahydro-carbazol-1'-ylidene)-propanedinitriles and aryl/heteroaryl carbaldehydes via vinylogous aldol reaction. The structures of the molecules were designated by FT-IR, 1H NMR, 13C NMR studies, elemental and X-ray crystallographic

  从不同的2-（2'，3'，4'，9'-四氢-咔唑- 1'-亚烷基）-丙二腈和芳基/杂芳基甲醛通过乙烯基醛醇缩合反应。分子的结构通过FT-IR，1 H NMR，13 C NMR研究，元素和X射线晶体学分析指定。已经筛选了合成的纯产物对抗生素抗性病原体的体外抗生物膜抑制活性。所有合成的化合物均显示出生物膜抑制作用。可能地，部分3a，3d和3h在生物膜抑制浓度（BIC）（200μg/ mL）下对细菌病原体表现出更高的抗生物膜活性。在三个部分中，图3a显示了对大肠杆菌生物膜的高期望值，最小和最大BIC百分比分别为32％（10μg/ mL）和89％（100μg/ mL），并选择了最低的BIC进行进一步评估。同样，在大肠杆菌生物膜中处理1小时后，3a会产生两倍的ROS。3a对HEK293细胞系中高达75μg/ mL的细胞活力无毒性作用。本研究的结果表明，在（E）-2-苄叉基-（Z）-咔唑基亚氨基氰乙酰胺中，（E）-2-苄叉基-6-甲基-2
• Amine-catalyzed direct assembly of indanedione-fused spirobenzo[<i>a</i>]carbazoles from α,α-dicyanomethylidenecarbazoles
  作者：Kripalaya Ratheesh Arya、Karnam Jayarampillai Rajendra Prasad

  DOI：10.1080/00397911.2019.1578887

  日期：2019.9.2

  Abstract An unprecedented amine-catalyzed stereoselective reaction of α,α-dicyanomethylidenecarbazoles with indane-1,3-dione and aryl/heteroaryl aldehydes afforded a series of indanedione-fused benzo[a]carbazoles. The plausible mechanism for the formation of the final products result from the above MCR is described based on successive Knoevenagel/Michael/nucleophilic reactions. The products were obtained

  摘要 α,α-二氰基亚甲基咔唑与茚满-1,3-二酮和芳基/杂芳基醛发生前所未有的胺催化立体选择性反应，得到了一系列茚二酮稠合的苯并[a]咔唑。基于连续的 Knoevenagel/Michael/亲核反应描述了上述 MCR 最终产物形成的合理机制。在不使用任何色谱技术的情况下以中等至良好的收率获得了产物。合成的螺环加合物的结构通过元素分析和光谱数据（FT-IR、1H NMR 和 13C NMR）确认。图形概要
• Design and synthesis of novel pyrrolo[2,3-a]carbazoles: 7-Chloro-2-oxo-3a-(2′-oxo-2′,3′-dihydro-1′H-indol-3′-yl)-2,3,3a,4,5,10-hexahydro-pyrrolo[3,2-a]carbazole-1-carbonitrile as an efficient anticancer agent
  作者：Perumal Sathiyachandran、Prasath Manogaran、Vladimir N. Nesterov、Viswanadha Vijaya Padma、Karnam Jayarampillai Rajendra Prasad

  DOI：10.1016/j.ejmech.2018.03.056

  日期：2018.4

  Highly efficient poly functionalized pyrrolo[3,2-a]carbazoles via ring contraction through rearrangement and intramolecular Michael addition reaction using one pot multicomponent reaction (MCR) is reported for the first time. Free radical scavenging and anticancer activities were determined by DPPH and MTT assays respectively. Of these, compound 8d exhibited most potent activity against HCT-15 human colon cancer cell lines with an IC50 value of 9.9 mu M and low toxicity toward normal human red blood cells. The morphological changes were visualized using scanning electron microscopy (SEM) technique, intracellular ROS generation measured by spectrofluorometer and gene expression levels of caspase-3, caspase-9 and Bcl-2 were determined using Semi quantitates PCR analysis for the target compound. Further, the structure activity relationships were also carried out. The results of the present study revealed that among pyrrolo[3,2-a]carbazole compounds, 7-chloro-2-oxo-3a-(2'-oxo-2',3'-dihydro-1'H-indol-3'-yl)2,3,3a,4,5,10-hexahydro-pyrrolo[3,2-a]carbazole-1-carbonitrile could be exploited as an excellent anticancer agent against colon cancer cells. (C) 2018 Published by Elsevier Masson SAS.