8-methyl-2-(p-tolylthio)quinoline-3-carbaldehyde | 1309388-94-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 8-methyl-2-(p-tolylthio)quinoline-3-carbaldehyde
• 英文别名: 8-Methyl-2-p-tolylsulfanyl-quinoline-3-carbaldehyde；8-methyl-2-(4-methylphenyl)sulfanylquinoline-3-carbaldehyde
• CAS: 1309388-94-0
• 化学式: C₁₈H₁₅NOS
• 分子量: 293.389
• InChiKey: SEYJTFWEXDOHLI-UHFFFAOYSA-N

物化性质

• 熔点：
  101.6-102.4 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• 沸点：
  465.4±45.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-methyl-2-(p-tolylthio)quinoline-3-carbaldehyde 、 丙烯酸甲酯（MA） 在 三乙烯二胺 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以98%的产率得到methyl 2-(hydroxy(8-methyl-2-(p-tolylthio)quinolin-3-yl)methyl)acrylate
  参考文献：
  名称：

  First construction of 12H-thiochromeno[2,3-b]quinolines and 5H-benzo[7,8]thiocino-[2,3-b]quinolines via intramolecular Friedel–Crafts reaction of Morita–Baylis–Hillman adducts

  摘要：

  An acid-promoted intramolecular Friedel Crafts reaction of the Morita-Baylis-Hillman adducts 3 derived from 2-arylthioquinolin-3-carbaldehydes 2 was investigated. Interestingly, promoted by sulfuric acid, the substrates with electron-donating groups on the aromatic ring gave six-membered fused-ring 12H-thiochromeno[2,3-b]quinolines 4 with good yields, while those with electron-withdrawing groups afforded eight-membered fused-ring 5H-benzo[7,8]thiocino[2,3-b]quinolines 5 in moderate yields. Using triflic acid instead of sulfuric acid, only products 4 could be obtained under the similar condition. (c) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.039
• 作为产物：
  描述：

  2-氯-8-甲基喹啉-3-甲醛 、 4-甲苯硫酚 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以81%的产率得到8-methyl-2-(p-tolylthio)quinoline-3-carbaldehyde
  参考文献：
  名称：

  First construction of 12H-thiochromeno[2,3-b]quinolines and 5H-benzo[7,8]thiocino-[2,3-b]quinolines via intramolecular Friedel–Crafts reaction of Morita–Baylis–Hillman adducts

  摘要：

  An acid-promoted intramolecular Friedel Crafts reaction of the Morita-Baylis-Hillman adducts 3 derived from 2-arylthioquinolin-3-carbaldehydes 2 was investigated. Interestingly, promoted by sulfuric acid, the substrates with electron-donating groups on the aromatic ring gave six-membered fused-ring 12H-thiochromeno[2,3-b]quinolines 4 with good yields, while those with electron-withdrawing groups afforded eight-membered fused-ring 5H-benzo[7,8]thiocino[2,3-b]quinolines 5 in moderate yields. Using triflic acid instead of sulfuric acid, only products 4 could be obtained under the similar condition. (c) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.039