(E,E)-3,5-十六碳二烯-2-酮 | 76003-15-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (E,E)-3,5-十六碳二烯-2-酮
• 英文名称: (E,E)-3,5-hexadecadien-2-one
• 英文别名: (3E,5E)-hexadeca-3,5-dien-2-one
• CAS: 76003-15-1
• 化学式: C₁₆H₂₈O
• 分子量: 236.398
• InChiKey: MXMINVKQOHRRSR-SQIWNDBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  17
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-甲基苯唑 、 (E,E)-3,5-十六碳二烯-2-酮 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 、 乙基苯 为溶剂， 反应 1.5h， 以38%的产率得到1-methyl-2-[(E,E)-1',3'-tetradecadienyl]-4(1H)-quinolone
  参考文献：
  名称：

  Design, synthesis and antimycobacterial activities of 1-methyl-2-alkenyl-4(1H)-quinolones

  摘要：

  A series of 23 new 1-methyl-2-alkenyl-4(1H)quinolones have been synthesized and evaluated in vitro for their antimycobacterial activities against fast growing species of mycobacteria, such as Mycobacterium fortuitum, M. smegmatis and M. phlei. The compounds displayed good to excellent inhibition of the growth of the mycobacterial test strains with improved antimycobacterial activity compared to the hit compound, evocarpine. The most active compounds, which possessed chain length of 11-13 carbons at position-2 displayed potent inhibitory effects with an MIC value of 1.0 mg/L. In a human diploid embryonic lung cell line, MRC-5 cytotoxicity assay, the alkaloids showed weak to moderate cytotoxic activity. Biological evaluation of these evocarpine analogues on the less pathogenic fast growing strains of mycobacteria showed an interesting antimycobacterial profile and provided significant insight into the structure-activity relationships. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.10.060
• 作为产物：
  描述：

  十一醛 以 四氢呋喃 、 乙腈 为溶剂， 反应 72.0h， 生成 (E,E)-3,5-十六碳二烯-2-酮
  参考文献：
  名称：

  Design, synthesis and antimycobacterial activities of 1-methyl-2-alkenyl-4(1H)-quinolones

  摘要：

  A series of 23 new 1-methyl-2-alkenyl-4(1H)quinolones have been synthesized and evaluated in vitro for their antimycobacterial activities against fast growing species of mycobacteria, such as Mycobacterium fortuitum, M. smegmatis and M. phlei. The compounds displayed good to excellent inhibition of the growth of the mycobacterial test strains with improved antimycobacterial activity compared to the hit compound, evocarpine. The most active compounds, which possessed chain length of 11-13 carbons at position-2 displayed potent inhibitory effects with an MIC value of 1.0 mg/L. In a human diploid embryonic lung cell line, MRC-5 cytotoxicity assay, the alkaloids showed weak to moderate cytotoxic activity. Biological evaluation of these evocarpine analogues on the less pathogenic fast growing strains of mycobacteria showed an interesting antimycobacterial profile and provided significant insight into the structure-activity relationships. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.10.060

文献信息

• A facile ring opening reaction of furfuryl selenides. Highly efficient method for dienones
  作者：Isao Kuwajima、Showay Hoshino、Toshihiko Tanaka、Makoto Shimizu

  DOI：10.1016/s0040-4039(00)77447-8

  日期：1980.1

  Treatment of furfuryl phenyl selenides with butyllithium or metallic lithium induces the facile ring opening reaction of their furan ring and the corresponding dienones are obtained in high yields.

  用丁基锂或金属锂处理糠基苯基硒化物可引发呋喃环的易开环反应，并以高收率获得相应的二烯酮。
• KUWAJIMA I.; HOSHINO S.; TANAKA T.; SHIMIZU M., TETRAHEDRON LETT., 1980, NO 21, 3209-3212
  作者：KUWAJIMA I.、 HOSHINO S.、 TANAKA T.、 SHIMIZU M.

  DOI：——

  日期：——
• Design, synthesis and antimycobacterial activities of 1-methyl-2-alkenyl-4(1H)-quinolones
  作者：Abraham A. Wube、Antje Hüfner、Christina Thomaschitz、Martina Blunder、Manfred Kollroser、Rudolf Bauer、Franz Bucar

  DOI：10.1016/j.bmc.2010.10.060

  日期：2011.1

  A series of 23 new 1-methyl-2-alkenyl-4(1H)quinolones have been synthesized and evaluated in vitro for their antimycobacterial activities against fast growing species of mycobacteria, such as Mycobacterium fortuitum, M. smegmatis and M. phlei. The compounds displayed good to excellent inhibition of the growth of the mycobacterial test strains with improved antimycobacterial activity compared to the hit compound, evocarpine. The most active compounds, which possessed chain length of 11-13 carbons at position-2 displayed potent inhibitory effects with an MIC value of 1.0 mg/L. In a human diploid embryonic lung cell line, MRC-5 cytotoxicity assay, the alkaloids showed weak to moderate cytotoxic activity. Biological evaluation of these evocarpine analogues on the less pathogenic fast growing strains of mycobacteria showed an interesting antimycobacterial profile and provided significant insight into the structure-activity relationships. (C) 2010 Elsevier Ltd. All rights reserved.