6-氯-2-甲基-4-苯基-1,4-二氢嘧啶-5-羧酸乙酯 | 100416-57-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 6-氯-2-甲基-4-苯基-1,4-二氢嘧啶-5-羧酸乙酯
• 英文名称: ethyl 6-chloro-2-methyl-4-phenyl-1,4-dihydropyrimidine-5-carboxylate
• CAS: 100416-57-7
• 化学式: C₁₄H₁₅ClN₂O₂
• 分子量: 278.738
• InChiKey: RFUWBHQLMHFJTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-氯-2-甲基-4-苯基-1,4-二氢嘧啶-5-羧酸乙酯 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium hydride 、 caesium carbonate 作用下， 以 N,N-二甲基乙酰胺 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 4.0h， 生成 1-tert-butyl 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：

  ethyl 2-methyl-4-phenyl-1,4,5,6-tetrahydropyrimidin-6-one-5-carboxylate 在 苯膦酰二氯 作用下， 反应 5.0h， 以60%的产率得到6-氯-2-甲基-4-苯基-1,4-二氢嘧啶-5-羧酸乙酯
  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

• 3N-substituted 3,4-dihydropyrimidine derivatives, processes for preparing them and pharmaceutical compositions
  申请人：SUNTORY LIMITED

  公开号：EP0157219A1

  公开（公告）日：1985-10-09

  A 3N-substituted 3,4-dihydropyrimidine derivative of the formula: wherein R' is methyl or ethyl, R2 is methyl or ethyl, R is phenyl or substituted phenyl, X is chloro or methyl and pharmaceutically acceptable acid addition salts thereof have in form of pharmaceutical compositions substantially the same strong vasodilative and Ca++ antagonistic effects as nicardipine and therefore are useful as agents for treating disorders of the cardiovascular system, for example, hypotensive agents, agents for amelioration of brain circulation and anti-angina pectoris agents. Processes for producing the above compounds economically and effectively are also disclosed.

  式中 R' 为甲基或乙基，R2 为甲基或乙基，R 为苯基或取代苯基，X 为氯或甲基的 3N 取代的 3,4-二氢嘧啶衍生物及其药学上可接受的酸加成盐在药物组合物形式上具有与尼卡地平基本相同的强血管扩张和 Ca++ 拮抗作用，因此可用作治疗心血管系统疾病的药物，例如降血压药、改善脑循环的药物和抗心绞痛药。 还公开了经济有效地生产上述化合物的工艺。
• Synthesis of novel 1,4-, 3,4-, and 4,5-dihydropyrimidines: First successful POCl3 chlorination and regioselective alkoxycarbonylation
  作者：Hidetsura Cho、Yoshiko Ohnaka、Mariko Hayashimatsu、Masaru Ueda、Keiyuu Shima

  DOI：10.1016/s0040-4039(00)87813-2

  日期：1986.1
• TE, SYUREHN;XAYASIMATSU, MARIKO;ISIXARA, TAKAFUMI
  作者：TE, SYUREHN、XAYASIMATSU, MARIKO、ISIXARA, TAKAFUMI

  DOI：——

  日期：——
• CHO HIDETSURA; OHNAKA YOSHIKO; HAYASHIMATSU MARIKO; UEDA MASARU; SHIMA KE+, TETRAHEDRON LETT., 27,(1986) N 52, 6377-6380
  作者：CHO HIDETSURA、 OHNAKA YOSHIKO、 HAYASHIMATSU MARIKO、 UEDA MASARU、 SHIMA KE+

  DOI：——

  日期：——
• JPS6064967A
  申请人：——

  公开号：JPS6064967A

  公开（公告）日：1985-04-13