4-(5-methoxymethoxypyridin-2-yl)piperazine-1-carboxylic acid benzyl ester | 915207-10-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4-(5-methoxymethoxypyridin-2-yl)piperazine-1-carboxylic acid benzyl ester
• CAS: 915207-10-2
• 化学式: C₁₉H₂₃N₃O₄
• 分子量: 357.409
• InChiKey: BLHMTXMGJWEWBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.52
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  64.13
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-(5-methoxymethoxypyridin-2-yl)piperazine-1-carboxylic acid benzyl ester 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 生成 4-(5-羟基吡啶-2-基)哌嗪-1-羧酸苄基酯
  参考文献：
  名称：

  Gram Scale Synthesis of the Glucuronide Metabolite of ABT-724

  摘要：

  A gram scale synthesis of the glucuronide metabolite of ABT-724 is reported. Glycosidic coupling between a trichloroacetimidate glucuronyl donor and a Cbz-protected hydroxypyridylpiperazine glycosyl acceptor is the key step in the synthesis, since attempts to directly glucuronidate the aglycon, aglycon derivatives, and other truncated glycosyl acceptors were unsuccessful. The route was used to produce 2.1 g of metabolite in eight steps from 2-chloro-5-hydroxypyridine in 21% overall yield.

  DOI：

  10.1021/jo0611972
• 作为产物：
  描述：

  2-氯-5-羟基吡啶 在 palladium diacetate potassium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 三乙胺 、 sodium t-butanolate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 41.0h， 生成 4-(5-methoxymethoxypyridin-2-yl)piperazine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  Gram Scale Synthesis of the Glucuronide Metabolite of ABT-724

  摘要：

  A gram scale synthesis of the glucuronide metabolite of ABT-724 is reported. Glycosidic coupling between a trichloroacetimidate glucuronyl donor and a Cbz-protected hydroxypyridylpiperazine glycosyl acceptor is the key step in the synthesis, since attempts to directly glucuronidate the aglycon, aglycon derivatives, and other truncated glycosyl acceptors were unsuccessful. The route was used to produce 2.1 g of metabolite in eight steps from 2-chloro-5-hydroxypyridine in 21% overall yield.

  DOI：

  10.1021/jo0611972