2-(4-isopropylphenylthio)-6-methylquinoline-3-carbaldehyde | 1309388-87-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(4-isopropylphenylthio)-6-methylquinoline-3-carbaldehyde
• CAS: 1309388-87-1
• 化学式: C₂₀H₁₉NOS
• 分子量: 321.443
• InChiKey: BMOCGIULIROTJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.63
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  29.96
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(4-isopropylphenylthio)-6-methylquinoline-3-carbaldehyde 在 三乙烯二胺 、 硫酸 作用下， 以 二氯甲烷 为溶剂， 反应 122.5h， 生成 methyl 2-(2-isopropyl-9-methyl-12H-thiochromeno[2,3-b]quinolin-12-yl)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-6-甲基喹啉-3-甲醛 、 对异丙基苯硫酚 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以69%的产率得到2-(4-isopropylphenylthio)-6-methylquinoline-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

文献信息

• 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
  作者：Weihui Zhong、Wang Ma、Yanbin Liu

  DOI：10.1016/j.tet.2011.03.039

  日期：2011.5

  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.