4-[(2-methylprop-2-en-1-yl)sulfanyl]quinazoline | 33238-81-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-[(2-methylprop-2-en-1-yl)sulfanyl]quinazoline
• 英文别名: 4-(2-methyl-allylsulfanyl)-quinazoline；4-(2-Methylprop-2-enylsulfanyl)quinazoline
• CAS: 33238-81-2
• 化学式: C₁₂H₁₂N₂S
• 分子量: 216.307
• InChiKey: LZNHLCNNCJVGNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[(2-methylprop-2-en-1-yl)sulfanyl]quinazoline 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Synthesis and Heterocyclization of 4-(Alkenylsulfanyl)quinazolines

  摘要：

  Alkylation of quinazoline-4(3H)-thione with 3-chloro-2-methylpropene and 2,3-dibromopropene afforded previously unknown 4-[(2-methylprop-2-en-1-yl)sulfanyl]quinazoline and 4-[(2-bromoprop-2-en-1-yl)sulfanyl]quinazoline, respectively. 4-[(Prop-2-en-1-yl)sulfanyl]quinazoline reacted with bromine to give bromocyclization product and product of bromine addition to the exocyclic double bond. The reaction of 4-[(2-methylprop-2-en-1-yl)sulfanyl]quinazoline with halogens involved thiazole ring fusion. 5-Bromo-3-methylidene-2,3-dihydro[1,3]thiazolo[3,2-c]quinazolinium bromide was isolated in the reaction of 4-[(2-bromoprop-2-en-1-yl)sulfanyl]quinazoline with bromine, and the reaction of the same substrate with iodine gave a mixture of 3-bromo-3-iodomethyl-2,3-dihydro[1,3]thiazolo[3,2-c]quinazolinium and 3-methylidene-2,3-dihydro[1,3]thiazolo[3,2-c]quinazolinium iodides. 4-[(2-Methylprop-2-en-1-yl)sulfanyl]quinazoline reacted with 2 equiv of iodine to produce 3-methyl-3-iodomethyl-2,3-dihydro[1,3]thiazolo[3,2-c]quinazolinium triiodide and pentaiodide; the structure of the latter was studied by X-ray diffraction.

  DOI：

  10.1134/s1070428020090018
• 作为产物：
  描述：

  4(3H)-喹唑啉硫酮 、 3-氯-2-甲基丙烯 在 potassium hydroxide 作用下， 以 水 、 异丙醇 为溶剂， 反应 3.0h， 以65%的产率得到4-[(2-methylprop-2-en-1-yl)sulfanyl]quinazoline
  参考文献：
  名称：

  Synthesis and Heterocyclization of 4-(Alkenylsulfanyl)quinazolines

  摘要：

  Alkylation of quinazoline-4(3H)-thione with 3-chloro-2-methylpropene and 2,3-dibromopropene afforded previously unknown 4-[(2-methylprop-2-en-1-yl)sulfanyl]quinazoline and 4-[(2-bromoprop-2-en-1-yl)sulfanyl]quinazoline, respectively. 4-[(Prop-2-en-1-yl)sulfanyl]quinazoline reacted with bromine to give bromocyclization product and product of bromine addition to the exocyclic double bond. The reaction of 4-[(2-methylprop-2-en-1-yl)sulfanyl]quinazoline with halogens involved thiazole ring fusion. 5-Bromo-3-methylidene-2,3-dihydro[1,3]thiazolo[3,2-c]quinazolinium bromide was isolated in the reaction of 4-[(2-bromoprop-2-en-1-yl)sulfanyl]quinazoline with bromine, and the reaction of the same substrate with iodine gave a mixture of 3-bromo-3-iodomethyl-2,3-dihydro[1,3]thiazolo[3,2-c]quinazolinium and 3-methylidene-2,3-dihydro[1,3]thiazolo[3,2-c]quinazolinium iodides. 4-[(2-Methylprop-2-en-1-yl)sulfanyl]quinazoline reacted with 2 equiv of iodine to produce 3-methyl-3-iodomethyl-2,3-dihydro[1,3]thiazolo[3,2-c]quinazolinium triiodide and pentaiodide; the structure of the latter was studied by X-ray diffraction.

  DOI：

  10.1134/s1070428020090018

文献信息

• Synthesis and Heterocyclization of 4-(Alkenylsulfanyl)quinazolines
  作者：E. I. Bakhteeva、D. G. Kim、V. V. Sharutin

  DOI：10.1134/s1070428020090018

  日期：2020.9

  Alkylation of quinazoline-4(3H)-thione with 3-chloro-2-methylpropene and 2,3-dibromopropene afforded previously unknown 4-[(2-methylprop-2-en-1-yl)sulfanyl]quinazoline and 4-[(2-bromoprop-2-en-1-yl)sulfanyl]quinazoline, respectively. 4-[(Prop-2-en-1-yl)sulfanyl]quinazoline reacted with bromine to give bromocyclization product and product of bromine addition to the exocyclic double bond. The reaction of 4-[(2-methylprop-2-en-1-yl)sulfanyl]quinazoline with halogens involved thiazole ring fusion. 5-Bromo-3-methylidene-2,3-dihydro[1,3]thiazolo[3,2-c]quinazolinium bromide was isolated in the reaction of 4-[(2-bromoprop-2-en-1-yl)sulfanyl]quinazoline with bromine, and the reaction of the same substrate with iodine gave a mixture of 3-bromo-3-iodomethyl-2,3-dihydro[1,3]thiazolo[3,2-c]quinazolinium and 3-methylidene-2,3-dihydro[1,3]thiazolo[3,2-c]quinazolinium iodides. 4-[(2-Methylprop-2-en-1-yl)sulfanyl]quinazoline reacted with 2 equiv of iodine to produce 3-methyl-3-iodomethyl-2,3-dihydro[1,3]thiazolo[3,2-c]quinazolinium triiodide and pentaiodide; the structure of the latter was studied by X-ray diffraction.