6-氯-2-甲基喹啉-3-羧酸甲酯 | 185501-93-3

• 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
• 中文名称: 6-氯-2-甲基喹啉-3-羧酸甲酯
• 英文名称: methyl 6-chloro-2-methylquinoline-3-carboxylate
• CAS: 185501-93-3
• 化学式: C₁₂H₁₀ClNO₂
• 分子量: 235.67
• InChiKey: FTICWUHEUGNFBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-氯-2-甲基喹啉-3-羧酸甲酯 在 sodium tetrahydroborate 作用下， 以 溶剂黄146 为溶剂， 反应 3.0h， 以50%的产率得到6-Chloro-2-methyl-1,2,3,4-tetrahydro-quinoline-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Reduction of 3-substituted 2-methylquinolines with sodium tetrahydroborate

  摘要：

  DOI：

  10.1007/bf01169232
• 作为产物：
  描述：

  2-氨基-5-氯苯甲醛 、 乙酰乙酸甲酯 在 lithium trifluoromethanesulfonate 作用下， 以 neat (no solvent) 为溶剂， 反应 0.17h， 以94%的产率得到6-氯-2-甲基喹啉-3-羧酸甲酯
  参考文献：
  名称：

  Lithium triflate (LiOTf): a highly efficient and reusable catalytic system for the synthesis of diversified quinolines under neat conditions

  摘要：

  A series of diverse polyfunctionalized quinolines were easily prepared in excellent yields via a Friedlander reaction of o-aminoaryl ketone or o-aminoaryl aldehyde with alpha-methylene ketones using lithium triflate as an expeditious catalyst under solvent free conditions. The protocol provides a practical and straightforward approach toward highly functionalized quinoline derivatives in excellent yields. The catalyst is easily recoverable and less sensitive to moisture, which makes this protocol more advantageous.

  DOI：

  10.1007/s00706-012-0906-2

文献信息

• Reduction of 3-substituted 2-methylquinolines with sodium tetrahydroborate
  作者：A. Sobolev、B. Vigante、Ya. Ozols、G. Duburs

  DOI：10.1007/bf01169232

  日期：1996.10
• Lithium triflate (LiOTf): a highly efficient and reusable catalytic system for the synthesis of diversified quinolines under neat conditions
  作者：Amol B. Atar、Someshwer D. Dindulkar、Yeon Tae Jeong

  DOI：10.1007/s00706-012-0906-2

  日期：2013.5

  A series of diverse polyfunctionalized quinolines were easily prepared in excellent yields via a Friedlander reaction of o-aminoaryl ketone or o-aminoaryl aldehyde with alpha-methylene ketones using lithium triflate as an expeditious catalyst under solvent free conditions. The protocol provides a practical and straightforward approach toward highly functionalized quinoline derivatives in excellent yields. The catalyst is easily recoverable and less sensitive to moisture, which makes this protocol more advantageous.