2-[(Z)-dec-3-ene-1,5-diynyl]pyrazine | 457914-52-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-[(Z)-dec-3-ene-1,5-diynyl]pyrazine
• 英文别名: 2-(3(Z)-decen-1,5-diynyl)pyrazine；2-(3-(Z)-dodecen-1,5-diynyl)pyrazine；2-[(Z)-dec-3-en-1,5-diynyl]pyrazine
• CAS: 457914-52-2
• 化学式: C₁₄H₁₄N₂
• 分子量: 210.279
• InChiKey: HVUZTXZHOMCVHD-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  sodium methylate 、 2-[(Z)-dec-3-ene-1,5-diynyl]pyrazine 在 四丁基碘化铵 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以34%的产率得到2-(2-butyl-6-methoxyphenyl)pyrazine
  参考文献：
  名称：

  Anionic Cycloaromatization of 1-Aryl-3-hexen-1,5-diynes Initiated by Methoxide Addition:  Synthesis of Phenanthridinones, Benzo[c]phenanthridinones, and Biaryls

  摘要：

  Treatment of 2-((Z)-6-substituted-3-hexene-1,5-diynyl)benzonitriles with sodium methoxide in refluxing methanol in the presence of a polar aprotic solvent, such as DMSO, HMPA, THF, or 18-crown-6, gave phenanthridinones in 21-77% yields. In these cases, addition of 10% DMSO into the reaction mixture gave the highest yield. On the other hand, methanolysis of 2-(2-(2-dalkynylphenyl)ethynyl)benzonitriles under the same reaction conditions gave benzo[c]phenanthridinones in 31-57% yields. Methanolysis of (Z)-1-aryl-3-hexen-1,5-diynes in the presence of 2 equiv of tetrabutylammonium iodide gave biaryls in 14-64% yields. It is found that the reactions with aryl groups bearing electron-withdrawing groups proceeded at greater rates and gave better yields.

  DOI：

  10.1021/jo010693h
• 作为产物：
  描述：

  1-butyl-4-chloro-3-buten-1-yne 在 四(三苯基膦)钯 copper(l) iodide 、 potassium carbonate 、 正丁胺 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 11.5h， 生成 2-[(Z)-dec-3-ene-1,5-diynyl]pyrazine
  参考文献：
  名称：

  Cytotoxicities and Topoisomerase I Inhibitory Activities of 2-[2-(2-Alkynylphenyl)ethynyl]benzonitriles, 1-Aryldec-3-ene-1,5-diynes, and Related Bis(enediynyl)arene Compounds

  摘要：

  The activities of a series of acyclic enediynes, 2-(6-substituted hex-3-ene-1,5-diynyl)benzonitriles (1-5) and their derivatives 7-23 were evaluated against several solid tumor cell lines and topoisomerase I. Compounds 1-5 show selective cytotoxicity with Hepa cells, and 2-[6-phenylhex-3-ene-1,5-diynyl]benzonitrile (5) reveals the most-potent activity. Analogues 8-10 and 13-22 also have the same effect with DLD cells; 1-[(Z)-dec-3-ene-1,5-diynyl]-4-nitrobenzene 21 shows the highest activity among them. Moreover, 1-[(Z)-dec-3-ene-1,5-diynyl]2-(trifluoromethyl)benzene (20) exhibits the strongest inhibitory activity with the Hela cell line. Derivatives 9, 10, 18, and 23 display inhibitory activities with topoisomerase I at 87 mum. The cell-cycle analysis of compound 5, which induces a significant blockage in S phase, indicates that these novel enediynes probably undergo other biological pathways leading to the cytotoxicity, except the inhibitory activity toward topoisomerase I.

  DOI：

  10.1002/1522-2675(200208)85:8<2564::aid-hlca2564>3.0.co;2-0

文献信息

• Anionic Cycloaromatization of 1-Aryl-3-hexen-1,5-diynes Initiated by Methoxide Addition:  Synthesis of Phenanthridinones, Benzo[<i>c</i>]phenanthridinones, and Biaryls
  作者：Ming-Jung Wu、Chi-Fong Lin、Wen-Der Lu

  DOI：10.1021/jo010693h

  日期：2002.8.1

  Treatment of 2-((Z)-6-substituted-3-hexene-1,5-diynyl)benzonitriles with sodium methoxide in refluxing methanol in the presence of a polar aprotic solvent, such as DMSO, HMPA, THF, or 18-crown-6, gave phenanthridinones in 21-77% yields. In these cases, addition of 10% DMSO into the reaction mixture gave the highest yield. On the other hand, methanolysis of 2-(2-(2-dalkynylphenyl)ethynyl)benzonitriles under the same reaction conditions gave benzo[c]phenanthridinones in 31-57% yields. Methanolysis of (Z)-1-aryl-3-hexen-1,5-diynes in the presence of 2 equiv of tetrabutylammonium iodide gave biaryls in 14-64% yields. It is found that the reactions with aryl groups bearing electron-withdrawing groups proceeded at greater rates and gave better yields.
• Cytotoxicities and Topoisomerase I Inhibitory Activities of 2-[2-(2-Alkynylphenyl)ethynyl]benzonitriles, 1-Aryldec-3-ene-1,5-diynes, and Related Bis(enediynyl)arene Compounds
  作者：Chi-Fong Lin、Wen-Der Lu、Pei-Chen Hsieh、Yao-Haur Kuo、Huey-Fen Chiu、Chyi-Jia Wang、Ming-Jung Wu

  DOI：10.1002/1522-2675(200208)85:8<2564::aid-hlca2564>3.0.co;2-0

  日期：2002.8

  The activities of a series of acyclic enediynes, 2-(6-substituted hex-3-ene-1,5-diynyl)benzonitriles (1-5) and their derivatives 7-23 were evaluated against several solid tumor cell lines and topoisomerase I. Compounds 1-5 show selective cytotoxicity with Hepa cells, and 2-[6-phenylhex-3-ene-1,5-diynyl]benzonitrile (5) reveals the most-potent activity. Analogues 8-10 and 13-22 also have the same effect with DLD cells; 1-[(Z)-dec-3-ene-1,5-diynyl]-4-nitrobenzene 21 shows the highest activity among them. Moreover, 1-[(Z)-dec-3-ene-1,5-diynyl]2-(trifluoromethyl)benzene (20) exhibits the strongest inhibitory activity with the Hela cell line. Derivatives 9, 10, 18, and 23 display inhibitory activities with topoisomerase I at 87 mum. The cell-cycle analysis of compound 5, which induces a significant blockage in S phase, indicates that these novel enediynes probably undergo other biological pathways leading to the cytotoxicity, except the inhibitory activity toward topoisomerase I.