2-[(5,5-dimethyl-3-oxocyclohexen-1-yl)amino]-4,5,6,7-tetrahydrobenzo[b]thiopene-3-carbonitrile | 384846-43-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2-[(5,5-dimethyl-3-oxocyclohexen-1-yl)amino]-4,5,6,7-tetrahydrobenzo[b]thiopene-3-carbonitrile
• 英文别名: 2-[(5,5-Dimethyl-3-oxocyclohexen-1-yl)amino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile；2-[(5,5-dimethyl-3-oxocyclohexen-1-yl)amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carbonitrile
• CAS: 384846-43-9
• 化学式: C₁₇H₂₀N₂OS
• 分子量: 300.425
• InChiKey: OQBPZFSLEMHYNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  81.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(5,5-dimethyl-3-oxocyclohexen-1-yl)amino]-4,5,6,7-tetrahydrobenzo[b]thiopene-3-carbonitrile 在 哌啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 为溶剂， 反应 8.33h， 生成 8-amino-2,2-dimethyl-4-oxo-5-phenyl-1,3,4,5,9,10,11,12-octahydro-2H-benzo[4',5']thieno[3',2':5,6]pyrimido[1,2-a]quinoline-6-carbonitrile
  参考文献：
  名称：

  摘要：

  The reactions of cyclic enaminoketones with benzylidenemalonitriles were examined and a new procedure was developed for the synthesis of fused heterocyclic systems containing the 1,4-dihydropyridine ring, viz., thienopyrimidoquinolines and furopyrimidoquinolines. The characteristic features of the reactions and the Structures Of the resulting compounds were investigated.

  DOI：

  10.1023/a:1015056117968
• 作为产物：
  描述：

  2-氨基-3-腈基-4,5,6,7--四氢苯并[B]噻吩 、 5,5-二甲基-1,3-环己二酮 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 5.0h， 以93%的产率得到2-[(5,5-dimethyl-3-oxocyclohexen-1-yl)amino]-4,5,6,7-tetrahydrobenzo[b]thiopene-3-carbonitrile
  参考文献：
  名称：

  摘要：

  The reactions of cyclic enaminoketones with benzylidenemalonitriles were examined and a new procedure was developed for the synthesis of fused heterocyclic systems containing the 1,4-dihydropyridine ring, viz., thienopyrimidoquinolines and furopyrimidoquinolines. The characteristic features of the reactions and the Structures Of the resulting compounds were investigated.

  DOI：

  10.1023/a:1015056117968

文献信息

• Cytotoxic and Antimicrobial Evaluations of Novel Apoptotic and Anti-Angiogenic Spiro Cyclic 2-Oxindole Derivatives of 2-Amino-tetrahydroquinolin-5-one
  作者：Said A. S. Ghozlan、Magda F. Mohamed、Ahmed G. Ahmed、Samia A. Shouman、Yasmin M. Attia、Ismail A. Abdelhamid

  DOI：10.1002/ardp.201400304

  日期：2015.2

  antimicrobial evaluations were performed on the prepared compounds. Most of these compounds exhibited high to moderate antimicrobial activity. With respect to the antitumor activity, the compounds showed more potent cytotoxic effect only toward the human breast cancer cell line MCF‐7. Also, we found that derivatives containing an ester group (8c, 11b, 14b, and 15b) are more active than those containing a

  制备了一系列包含 2-氨基-四氢喹啉-5-one 的新型环状 2-羟吲哚衍生物。使用不同的光谱工具阐明了制备的化合物的结构。通过NOE差异实验和通过使用邻位取代基影响进一步环化，阐明了反应产物的区域取向。对制备的化合物进行了抗肿瘤和抗菌评估。大多数这些化合物表现出高到中等的抗微生物活性。在抗肿瘤活性方面，这些化合物仅对人乳腺癌细胞系 MCF-7 显示出更有效的细胞毒作用。此外，我们发现含有酯基的衍生物（8c、11b、14b 和 15b）比含有氰化物基团的衍生物（8a、11a、14a 和 15a）更具活性。而且，化合物 15b 和 8b 是该组中活性最强的衍生物。这两种化合物通过 DNA 片段化、肿瘤抑制蛋白 p53 的诱导、caspase-9 的诱导，以及最终通过降低血管内皮生长因子的表达和分泌来抑制血管生成，从而抑制人乳腺癌 MCF-7 细胞的增殖。 .
• Regioorientation in the Addition Reaction of α-Substituted Cinnamonitrile to Enamines Utilizing Chitosan as a Green Catalyst: Unambiguous Structural Characterization Using 2D-HMBC NMR Spectroscopy
  作者：Said A. S. Ghozlan、Ahmed Gamal Ahmed、Ismail Abdelshafy Abdelhamid

  DOI：10.1002/jhet.2341

  日期：2016.5

  good to excellent yields by proceeding through a simple, mild, and efficient procedure including the reaction of enamines with substituted cinnamonitriles using DABCO, piperidine, or chitosan as catalysts. The regioorientation of Michael addition was established with no doubt using the 2D‐HMBC spectroscopy.

  六氢喹啉及其稠合衍生物可通过简单，温和和有效的方法进行，包括使用DABCO，哌啶或脱乙酰壳多糖作为催化剂，使烯胺与取代的肉桂腈反应，从而获得高至优异的收率。毫无疑问，使用2D-HMBC光谱确定了迈克尔加成的区域取向。
• Three-component synthesis of 5-aryl-1,8-naphthyridine-3-carbonitriles
  作者：A. Yu. Alekseeva、D. L. Mikhailov、I. N. Bardasov、D. V. Timrukova、O. V. Ershov

  DOI：10.1134/s1070428016100158

  日期：2016.10

  A procedure has been developed for the synthesis of highly functionalized 1,8-naphthyridines by three-component condensation of aromatic aldehydes with malononitrile dimer and enamino ketones.
• ——
  作者：B. V. Lichitsky、S. N. Ivanov、A. A. Dudinov、S. A. Woznesensky、M. M. Krayushkin

  DOI：10.1023/a:1015056117968

  日期：——

  The reactions of cyclic enaminoketones with benzylidenemalonitriles were examined and a new procedure was developed for the synthesis of fused heterocyclic systems containing the 1,4-dihydropyridine ring, viz., thienopyrimidoquinolines and furopyrimidoquinolines. The characteristic features of the reactions and the Structures Of the resulting compounds were investigated.