3-methyl-4-(methylthio)isoquinoline | 133100-88-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 3-methyl-4-(methylthio)isoquinoline
• 英文别名: 3-Methyl-4-methylsulfanylisoquinoline
• CAS: 133100-88-6
• 化学式: C₁₁H₁₁NS
• 分子量: 189.281
• InChiKey: ZMWSBNHXHBZBFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  38.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-甲基异喹啉 在 氢溴酸 、 溴 作用下， 以 二甲基亚砜 为溶剂， 反应 7.0h， 生成 3-methyl-4-(methylthio)isoquinoline
  参考文献：
  名称：

  Nature of the reactions involving 4-haloisoquinolines and amide ion in ammonia. Remarkable competition between SRN1 substitution and .sigma. complex formation

  摘要：

  4-Bromo- (1) or 4-chloroisoquinoline (3) in refluxing liquid ammonia containing amide and thiomethoxide ions reacts preferentially with the thiolate ion to give 4-(methylthio)isoquinoline (2) in high yield. The bromo substrate was shown to require amide ion in order to react with thiomethoxide ion, no reaction taking place in its absence. Substitution product is believed to form from both halides by an S(RN)1 mechanism. By contrast, 3-chloroisoquinoline under the same conditions of mixed anions gives 3-aminoisoquinoline. The role of amide ion and its addition to give sigma complexes in these and other reactions of 4-halogenated isoquinolines in ammonia is discussed.

  DOI：

  10.1021/jo00008a042

文献信息

• ZOLTEWICZ, JOHN A.;OESTREICH, TERENCE M., J. ORG. CHEM., 56,(1991) N, C. 2805-2809
  作者：ZOLTEWICZ, JOHN A.、OESTREICH, TERENCE M.

  DOI：——

  日期：——