(2-chloro-4-methoxypyridin-3-yl)-bis-[2-(methylsulfayl)pyrimidin-4-yl]methyl acetate | 864229-50-5

• 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-chloro-4-methoxypyridin-3-yl)-bis-[2-(methylsulfayl)pyrimidin-4-yl]methyl acetate
• 英文别名: [(2-Chloro-4-methoxypyridin-3-yl)-bis(2-methylsulfanylpyrimidin-4-yl)methyl] acetate
• CAS: 864229-50-5
• 化学式: C₁₉H₁₈ClN₅O₃S₂
• 分子量: 463.969
• InChiKey: WTNPESKCHDJIQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  151
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2-chloro-4-methoxypyridin-3-yl)-bis-[2-(methylsulfayl)pyrimidin-4-yl]methyl acetate 在 三乙基硅烷 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 氯仿 、 1,2-二氯乙烷 为溶剂， 反应 41.0h， 生成 4-methoxy-9-(4-methoxybenzylamino)-5-[2-(4-methoxybenzylamino)pyrimidin-4-yl]pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine
  参考文献：
  名称：

  Concise Total Syntheses of Variolin B and Deoxyvariolin B

  摘要：

  The total synthesis of the marine alkaloid variolin B has been achieved in 8 steps and 17% overall yield, starting from commercially available 4-chloro-2-methylthiopyrimidine. The key reaction involves the tandem deoxygenation and cyclization of a triarylmethanol using a combination of triethylsilane and trifluoroacetic acid. In addition, the deoxygenated analogue was prepared in 6 steps and 23% overall yield, starting from the same starting material.

  DOI：

  10.1021/jo050523v
• 作为产物：
  描述：

  4-甲氧基吡啶-N-氧化物 在 正丁基锂 、 三氯氧磷 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 20.5h， 生成 (2-chloro-4-methoxypyridin-3-yl)-bis-[2-(methylsulfayl)pyrimidin-4-yl]methyl acetate
  参考文献：
  名称：

  Concise Total Syntheses of Variolin B and Deoxyvariolin B

  摘要：

  The total synthesis of the marine alkaloid variolin B has been achieved in 8 steps and 17% overall yield, starting from commercially available 4-chloro-2-methylthiopyrimidine. The key reaction involves the tandem deoxygenation and cyclization of a triarylmethanol using a combination of triethylsilane and trifluoroacetic acid. In addition, the deoxygenated analogue was prepared in 6 steps and 23% overall yield, starting from the same starting material.

  DOI：

  10.1021/jo050523v

文献信息

• Concise Total Syntheses of Variolin B and Deoxyvariolin B
  作者：Regan J. Anderson、Jonathan B. Hill、Jonathan C. Morris

  DOI：10.1021/jo050523v

  日期：2005.8.1

  The total synthesis of the marine alkaloid variolin B has been achieved in 8 steps and 17% overall yield, starting from commercially available 4-chloro-2-methylthiopyrimidine. The key reaction involves the tandem deoxygenation and cyclization of a triarylmethanol using a combination of triethylsilane and trifluoroacetic acid. In addition, the deoxygenated analogue was prepared in 6 steps and 23% overall yield, starting from the same starting material.