1-methyl-2-[(E)-1'-heptenyl]-4(1H)-quinolone | 115869-45-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-methyl-2-[(E)-1'-heptenyl]-4(1H)-quinolone
• 英文别名: 2-[(E)-hept-1-enyl]-1-methyl-quinolin-4-one；2-[(E)-hept-1-enyl]-1-methylquinolin-4-one
• CAS: 115869-45-9
• 化学式: C₁₇H₂₁NO
• 分子量: 255.36
• InChiKey: SKUSRLVFRZBWDI-JXMROGBWSA-N

物化性质

• 沸点：
  373.2±42.0 °C(predicted)
• 密度：
  1.077±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-甲基苯唑 在 15-冠醚-5 正丁基锂 、 sodium hydride 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 生成 1-methyl-2-[(E)-1'-heptenyl]-4(1H)-quinolone
  参考文献：
  名称：

  The Chemistry of 2H-3,1-Benzoxazine-2,4(1H)-dione (Isatoic Anhydride). 20¹. Synthesis and Wittig Reactions of Dimethyl (4-Oxo-1,4-dihydro-Quinolin-2-yl)methanephosphonates

  摘要：

  异阿托酸酐与二锂化的2-氧代烷基膦酸酯反应，生成二甲基（4-氧代-1，4-二氢喹啉-2-基）甲基膦酸酯5。这些膦酸酯经过Horner反应与醛反应，以良好的产率生成2-（1-烯基）-4（1H）-喹啉酮10。

  DOI：

  10.1055/s-1988-27474

文献信息

• 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.
• The Chemistry of 2<i>H</i>-3,1-Benzoxazine-2,4(1<i>H</i>)-dione (Isatoic Anhydride). 20¹. Synthesis and Wittig Reactions of Dimethyl (4-Oxo-1,4-dihydro-Quinolin-2-yl)methanephosphonates
  作者：Gary M. Coppola

  DOI：10.1055/s-1988-27474

  日期：——

  Isatoic anhydrides react with dilithiated 2-oxoalkanephosphonates to give dimethyl (4-oxo-1,4-dihydroquinolin-2-yl)methanephosphonates 5. These phosphonates undergo a Horner reaction with aldehydes to produce 2-(1-alkenyl)-4(1H)- quinolinones 10 in good yields.

  异阿托酸酐与二锂化的2-氧代烷基膦酸酯反应，生成二甲基（4-氧代-1，4-二氢喹啉-2-基）甲基膦酸酯5。这些膦酸酯经过Horner反应与醛反应，以良好的产率生成2-（1-烯基）-4（1H）-喹啉酮10。