6,6-Bis(hydroxymethyl)-2-(4-methoxyphenyl)-7,8-dihydroquinolin-5-one | 1276536-43-6

• 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: 6,6-Bis(hydroxymethyl)-2-(4-methoxyphenyl)-7,8-dihydroquinolin-5-one
• CAS: 1276536-43-6
• 化学式: C₁₈H₁₉NO₄
• 分子量: 313.353
• InChiKey: CLNISOLEXONWRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  79.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-(dimethylamino)-1-(4-methoxyphenyl)prop-2-en-1-one 在 cerium(III) chloride heptahydrate 、 ammonium acetate 、 L-脯氨酸 、 sodium iodide 、 sodium hydroxide 作用下， 以 水 、 异丙醇 为溶剂， 生成 6,6-Bis(hydroxymethyl)-2-(4-methoxyphenyl)-7,8-dihydroquinolin-5-one
  参考文献：
  名称：

  Synthesis and antitubercular evaluation of novel substituted aryl and thiophenyl tethered dihydro-6H-quinolin-5-ones

  摘要：

  A series of novel aryl and thiophenyl tethered dihydro-6H-quinolin-5-ones have been synthesized in very good yields through CeCl3 center dot 7H(2)O-NaI catalyzed one-pot condensation of beta-enaminones derived from the respective methyl ketones; 1,3-cyclohexanedione & 5,5-dimethyl-1,3-cyclohexanedione and ammonium acetate refluxing in 2-propanol. Dihydro-6H-quinolin-5-ones 3a-f was further derivatized to the respective hydroxymethyl analogs using proline as an organocatalyst in aqueous media. Among the all 18 compounds screened for in vitro antimycobacterial activity against Mycobacterium tuberculosis H(37)Rv (MTB), dihydro-6H-quinolin-5-ones 4e and 4f were found to be most active with MIC 3.13 mu g/mL. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.082

文献信息

• Synthesis and antitubercular evaluation of novel substituted aryl and thiophenyl tethered dihydro-6H-quinolin-5-ones
  作者：Srinivas Kantevari、Santhosh Reddy Patpi、Balasubramanian Sridhar、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.bmcl.2010.12.082

  日期：2011.2

  A series of novel aryl and thiophenyl tethered dihydro-6H-quinolin-5-ones have been synthesized in very good yields through CeCl3 center dot 7H(2)O-NaI catalyzed one-pot condensation of beta-enaminones derived from the respective methyl ketones; 1,3-cyclohexanedione & 5,5-dimethyl-1,3-cyclohexanedione and ammonium acetate refluxing in 2-propanol. Dihydro-6H-quinolin-5-ones 3a-f was further derivatized to the respective hydroxymethyl analogs using proline as an organocatalyst in aqueous media. Among the all 18 compounds screened for in vitro antimycobacterial activity against Mycobacterium tuberculosis H(37)Rv (MTB), dihydro-6H-quinolin-5-ones 4e and 4f were found to be most active with MIC 3.13 mu g/mL. (C) 2010 Elsevier Ltd. All rights reserved.