3(Z)-decen-1,5-diynylbenzene | 368430-36-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3(Z)-decen-1,5-diynylbenzene
• 英文别名: [(Z)-dec-3-en-1,5-diynyl]benzene
• CAS: 368430-36-8
• 化学式: C₁₆H₁₆
• 分子量: 208.303
• InChiKey: MXOHWYHLLOIIHR-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  sodium methylate 、 3(Z)-decen-1,5-diynylbenzene 在 四丁基碘化铵 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以14%的产率得到(2-butyl-6-methoxyphenyl)benzene
  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：

  (3Z)-1-(trimethylsilyl)-dec-3-en-1,5-diyne 在 copper(l) iodide 、 四(三苯基膦)钯 、 potassium carbonate 、 正丁胺 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 3(Z)-decen-1,5-diynylbenzene
  参考文献：
  名称：

  （Z）-1-芳基-3-己烯-1，5-二炔与叠氮化钠的反应：1-芳基-1H-苯并三唑的合成。

  摘要：

  [反应：参见正文]通过（Z）-的处理，完成了涉及1,3-偶极环加成反应，阴离子环化和σ重排的新型串联级联反应，用于合成1-芳基-1H-苯并三唑2和3。 1-芳基-3-henen-1,5-二炔（1）与叠氮化钠在DMF或DMSO中在80摄氏度下反应12小时，收率65-91％。

  DOI：

  10.1021/ol047563q

文献信息

• A Series of Enediynes as Novel Inhibitors of Topoisomerase I
  作者：Chi-Fong Lin、Pei-Chen Hsieh、Wen-Der Lu、Huey-Fen Chiu、Ming-Jung Wu

  DOI：10.1016/s0968-0896(01)00081-5

  日期：2001.7

  A series of acyclic enediynes, 2-((6-substituted)-3-hexen- 1,5-diynyl)benzonitriles (8-11), display potent inhibition against topoisomerase I without the formation of active biradical intermediates and show inhibitory activity against topoisomerase I at 10 muM, which is five times that of camptothecin from the results of agarose gel electrophoresis. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 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.
• Reaction of (<i>Z</i>)-1-Aryl-3-hexen-1,5-diynes with Sodium Azide:  Synthesis of 1-Aryl-1<i>H</i>-benzotriazoles
  作者：Zhong-Yi Chen、Ming-Jung Wu

  DOI：10.1021/ol047563q

  日期：2005.2.1

  [reaction: see text] A novel tandem cascade reaction involving 1,3-dipolar cycloaddition reaction, anionic cyclization, and sigmatropic rearrangement for the synthesis of 1-aryl-1H-benzotriazoles 2 and 3 was accomplished by treatment of the (Z)-1-aryl-3-henen-1,5-diynes (1) with sodium azide in DMF or DMSO at 80 degrees C for 12 h and gives 65-91% yields.

  [反应：参见正文]通过（Z）-的处理，完成了涉及1,3-偶极环加成反应，阴离子环化和σ重排的新型串联级联反应，用于合成1-芳基-1H-苯并三唑2和3。 1-芳基-3-henen-1,5-二炔（1）与叠氮化钠在DMF或DMSO中在80摄氏度下反应12小时，收率65-91％。