1-[(Z)-dec-3-ene-1,5-diynyl]-4-nitrobenzene | 457914-53-3

• 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-nitrobenzene
• 英文别名: 4-(3(Z)-decen-1,5-diynyl)nitrobenzene；4-nitro-1-(3-(Z)-dodecen-1,5-diynyl)benzene；1-[(Z)-dec-3-en-1,5-diynyl]-4-nitrobenzene
• CAS: 457914-53-3
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: OTWJCQYEDLXPNC-FPLPWBNLSA-N

物化性质

• 沸点：
  378.2±42.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  19
• 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：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[(Z)-dec-3-ene-1,5-diynyl]-4-nitrobenzene 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以61%的产率得到7-butyl-1-(4-nitrophenyl)-1H-benzo[d][1,2,3]triazole
  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
• 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 1-[(Z)-dec-3-ene-1,5-diynyl]-4-nitrobenzene
  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

• 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％。