2-methylthio-3-bromoquinoline

• 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: 2-methylthio-3-bromoquinoline
• 英文别名: 3-bromo-2-(methylsulfanyl)quinoline；3-Bromo-2-(methylthio)quinoline；3-bromo-2-methylsulfanylquinoline
• 化学式: C₁₀H₈BrNS
• 分子量: 254.15
• InChiKey: WEBZVLGAGARWEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  38.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methylthio-3-bromoquinoline 在 正丁基锂 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.33h， 生成 (4-methoxyphenyl)[2-(methylsulfanyl)quinolin-3-yl]methanone
  参考文献：
  名称：

  2-(2,2-二溴乙烯)苯基异硫氰酸酯与丁基锂反应合成3-溴喹啉-2(1H)-硫酮和2-(烷基硫烷基)-3-溴喹啉

  摘要：

  The synthesis of 3-bromoquinoline-2(1H)-thiones and 2-(alkylsulfanyl)-3-bromoquinolines from readily available starting materials was accomplished. Thus, 2-(2,2-dibromoethenyl)phenyl isothiocyanates were treated with butyllithium to afford, after aqueous workup, 3-bromoquinoline-2(1H)-thiones. When haloalkanes were added prior to workup, 2-(alkylsulfanyl)-3-bromoquinolines were obtained. An elaboration of one of these compounds to a thieno[2,3-b]quinoline derivative and one-pot preparation of 3-substituted quinoline-2(1H)-thiones were also achieved.

  DOI：

  10.3987/com-16-s(s)3
• 作为产物：
  描述：

  3-溴-2-氯喹啉 在 sodium hydroxide 、 硫脲 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成 2-methylthio-3-bromoquinoline
  参考文献：
  名称：

  Nowak, Malgorzata; Pluta, Krystian; Kloc, Christian, Heterocycles, 2003, vol. 60, # 9, p. 2045 - 2056

  摘要：

  DOI：

文献信息

• Synthesis of 3-Bromoquinoline-2(1H)-thiones and 2-(Alkylsulfanyl)-3-bromoquinolines Based on the Reaction of 2-(2,2-Dibromoethenyl)phenyl Isothiocyanates with Butyllithium
  作者：Kazuhiro Kobayashi、Ippei Nozawa、Takashi Nogi

  DOI：10.3987/com-16-s(s)3

  日期：——

  The synthesis of 3-bromoquinoline-2(1H)-thiones and 2-(alkylsulfanyl)-3-bromoquinolines from readily available starting materials was accomplished. Thus, 2-(2,2-dibromoethenyl)phenyl isothiocyanates were treated with butyllithium to afford, after aqueous workup, 3-bromoquinoline-2(1H)-thiones. When haloalkanes were added prior to workup, 2-(alkylsulfanyl)-3-bromoquinolines were obtained. An elaboration of one of these compounds to a thieno[2,3-b]quinoline derivative and one-pot preparation of 3-substituted quinoline-2(1H)-thiones were also achieved.
• Nowak, Malgorzata; Pluta, Krystian; Kloc, Christian, Heterocycles, 2003, vol. 60, # 9, p. 2045 - 2056
  作者：Nowak, Malgorzata、Pluta, Krystian、Kloc, Christian、Siegrist, Theo

  DOI：——

  日期：——