1-tert-butyl 5-ethyl 4-chloro-2-methyl-6-phenyl-1,6-dihydropyrimidine-1,5-dicarboxylate | 1337541-30-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-tert-butyl 5-ethyl 4-chloro-2-methyl-6-phenyl-1,6-dihydropyrimidine-1,5-dicarboxylate
• 英文别名: 3-O-tert-butyl 5-O-ethyl 6-chloro-2-methyl-4-phenyl-4H-pyrimidine-3,5-dicarboxylate
• CAS: 1337541-30-6
• 化学式: C₁₉H₂₃ClN₂O₄
• 分子量: 378.856
• InChiKey: AYMOPAFCQYGSGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  68.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-tert-butyl 5-ethyl 4-chloro-2-methyl-6-phenyl-1,6-dihydropyrimidine-1,5-dicarboxylate 在 bis-triphenylphosphine-palladium(II) chloride 、 caesium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基乙酰胺 为溶剂， 反应 5.0h， 生成 5-ethyl 2-methyl-6-phenyl-4-(thiophen-3-yl)-1,6-dihydropyrimidine-1,5-dicarboxylate
  参考文献：
  名称：

  Synthesis and Substitution Reactions of 4(6)-Chlorodihydropyrimidines

  摘要：

  Chlorination of the corresponding ketones with phenylphosphonic dichloride (PhPOCl2) provided ethyl 6(4)-chloro-2-methyl-4(6)-phenyl-1,4(6)dihydropyrimidine-5-carboxylate in good yield. The cross-coupling reactions of organoboronic acids or triethylborane with 1-tert-butyl 5-ethyl 4-chloro-2-methyl-6-phenyl-1,6-dihydropyrimidine-1,5-dicarboxylate synthesized by regiospecific alkoxycarbonylation of the chlorinated dihydropyrimidine afforded 1,4(3,4)-dihydropyrimidines having a variety of functional groups at position-6(4) in good to excellent yields.

  DOI：

  10.3987/com-11-12244
• 作为产物：
  描述：

  丙二酸二乙酯 在 哌啶 、 苯膦酰二氯 、 sodium ethanolate 、 sodium hydride 、 苯甲酸 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 7.0h， 生成 1-tert-butyl 5-ethyl 4-chloro-2-methyl-6-phenyl-1,6-dihydropyrimidine-1,5-dicarboxylate
  参考文献：
  名称：

  Synthesis and Substitution Reactions of 4(6)-Chlorodihydropyrimidines

  摘要：

  Chlorination of the corresponding ketones with phenylphosphonic dichloride (PhPOCl2) provided ethyl 6(4)-chloro-2-methyl-4(6)-phenyl-1,4(6)dihydropyrimidine-5-carboxylate in good yield. The cross-coupling reactions of organoboronic acids or triethylborane with 1-tert-butyl 5-ethyl 4-chloro-2-methyl-6-phenyl-1,6-dihydropyrimidine-1,5-dicarboxylate synthesized by regiospecific alkoxycarbonylation of the chlorinated dihydropyrimidine afforded 1,4(3,4)-dihydropyrimidines having a variety of functional groups at position-6(4) in good to excellent yields.

  DOI：

  10.3987/com-11-12244

文献信息

• Synthesis and Substitution Reactions of 4(6)-Chlorodihydropyrimidines
  作者：Hidetsura Cho、Yoshizumi Yasui、Satoshi Kobayashi、Masahiko Yamaguchi、Eunsang Kwon、Mieko Arisawa

  DOI：10.3987/com-11-12244

  日期：——

  Chlorination of the corresponding ketones with phenylphosphonic dichloride (PhPOCl2) provided ethyl 6(4)-chloro-2-methyl-4(6)-phenyl-1,4(6)dihydropyrimidine-5-carboxylate in good yield. The cross-coupling reactions of organoboronic acids or triethylborane with 1-tert-butyl 5-ethyl 4-chloro-2-methyl-6-phenyl-1,6-dihydropyrimidine-1,5-dicarboxylate synthesized by regiospecific alkoxycarbonylation of the chlorinated dihydropyrimidine afforded 1,4(3,4)-dihydropyrimidines having a variety of functional groups at position-6(4) in good to excellent yields.