N'-((5-bromopyridin-3-yl)methylene)-4-methylbenzenesulfonohydrazide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N'-((5-bromopyridin-3-yl)methylene)-4-methylbenzenesulfonohydrazide
• 英文别名: N-[(5-bromopyridin-3-yl)methylideneamino]-4-methylbenzenesulfonamide
• 化学式: C₁₃H₁₂BrN₃O₂S
• 分子量: 354.227
• InChiKey: GUJXBULLJBUOEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.46
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  71.42
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  异丙基硼酸 、 N'-((5-bromopyridin-3-yl)methylene)-4-methylbenzenesulfonohydrazide 在 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以25 mg的产率得到3-bromo-5-isobutylpyridine
  参考文献：
  名称：

  A General C(sp³)–C(sp³) Cross-Coupling of Benzyl Sulfonylhydrazones with Alkyl Boronic Acids

  摘要：

  A general transition-metal-free cross-coupling between benzylic sulfonylhydrazones and 1 degrees, 2 degrees, or 3 degrees alkyl boronic acids is reported. The base-promoted reaction is operationally simple and exhibits a broad substrate scope to forge a variety of alkyl-alkyl bonds, including between sterically encumbered secondary and tertiary sp(3)-carbons. The ability of this method to simplify retrosynthetic analysis is exemplified by the improved synthesis of multiple medicinally relevant scaffolds.

  DOI：

  10.1021/acs.orglett.0c00471
• 作为产物：
  描述：

  5-溴吡啶-3-甲醛 、 对甲苯磺酰肼 以 甲醇 为溶剂， 反应 12.0h， 生成 N'-((5-bromopyridin-3-yl)methylene)-4-methylbenzenesulfonohydrazide
  参考文献：
  名称：

  A General C(sp³)–C(sp³) Cross-Coupling of Benzyl Sulfonylhydrazones with Alkyl Boronic Acids

  摘要：

  A general transition-metal-free cross-coupling between benzylic sulfonylhydrazones and 1 degrees, 2 degrees, or 3 degrees alkyl boronic acids is reported. The base-promoted reaction is operationally simple and exhibits a broad substrate scope to forge a variety of alkyl-alkyl bonds, including between sterically encumbered secondary and tertiary sp(3)-carbons. The ability of this method to simplify retrosynthetic analysis is exemplified by the improved synthesis of multiple medicinally relevant scaffolds.

  DOI：

  10.1021/acs.orglett.0c00471