1-[(Z)-dec-3-ene-1,5-diynyl]-4-(trifluoromethyl)benzene | 457914-45-3

• 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: 1-[(Z)-dec-3-ene-1,5-diynyl]-4-(trifluoromethyl)benzene
• 英文别名: 4-(3(Z)-decen-1,5-diynyl)(trifluoromethyl)benzene；(Z)-1-(deca-3-en-1,5-diynyl)-4-(trifluoromethyl)benzene；4-(3-(Z)-dodecen-1,5-diynyl)trifluoromethylbenzene；1-[(Z)-dec-3-en-1,5-diynyl]-4-(trifluoromethyl)benzene
• CAS: 457914-45-3
• 化学式: C₁₇H₁₅F₃
• 分子量: 276.301
• InChiKey: HTXRPMJRIRWATG-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  20
• 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：
  0
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[(Z)-dec-3-ene-1,5-diynyl]-4-(trifluoromethyl)benzene 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以32%的产率得到7-butyl-3-(4-(trifluoromethyl)phenyl)-[1,2,3]triazolo[1,5-a]pyridine
  参考文献：
  名称：

  叠氮化钠促进对映体的杂环化：一个X射线数据含混不清的案例和结构修订

  摘要：

  已经表明，与文献数据相反，叠氮化钠促进的（Z）-1-芳基-3-己烯-1,5-二炔串联环化导致形成相应的[1,2,3]三唑[1,5- a ]吡啶，而不是1 H-苯并三唑衍生物。显然，先前研究人员做出的不正确的结构解释是由于对X射线数据的错误解释造成的。讨论了这种类型的许多新转化以及X射线和NMR实验。

  DOI：

  10.1021/ol500125j
• 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 1-[(Z)-dec-3-ene-1,5-diynyl]-4-(trifluoromethyl)benzene
  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

• 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.
• 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％。
• Heterocyclization of Enediynes Promoted by Sodium Azide: A Case of Ambiguity of X-ray Data and Structure Revision
  作者：Anna V. Gulevskaya、Alexander S. Tyaglivy、Alexander F. Pozharskii、Julia I. Nelina-Nemtseva、Dmitry V. Steglenko

  DOI：10.1021/ol500125j

  日期：2014.3.21

  It has been shown that contrary to the literature data the tandem cyclization of (Z)-1-aryl-3-hexen-1,5-diynes promoted by sodium azide results in the formation of the corresponding [1,2,3]triazolo[1,5-a]pyridines, not 1H-benzotriazole derivatives. Apparently, incorrect structure elucidation made by previous investigators originates from misinterpretation of X-ray data. A number of new transformations

  已经表明，与文献数据相反，叠氮化钠促进的（Z）-1-芳基-3-己烯-1,5-二炔串联环化导致形成相应的[1,2,3]三唑[1,5- a ]吡啶，而不是1 H-苯并三唑衍生物。显然，先前研究人员做出的不正确的结构解释是由于对X射线数据的错误解释造成的。讨论了这种类型的许多新转化以及X射线和NMR实验。