ethyl 4-(4-bromophenyl)-6-formyl-1,2,3,4-tetrahydro-2-oxopyrimidine-5-carboxylate | 1443444-49-2

• 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: ethyl 4-(4-bromophenyl)-6-formyl-1,2,3,4-tetrahydro-2-oxopyrimidine-5-carboxylate
• CAS: 1443444-49-2
• 化学式: C₁₄H₁₃BrN₂O₄
• 分子量: 353.172
• InChiKey: DVTQYMAJKWCYCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.82
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  84.5
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 4-(4-bromophenyl)-6-formyl-1,2,3,4-tetrahydro-2-oxopyrimidine-5-carboxylate 在 一水合肼 作用下， 以80%的产率得到4-(4-bromophenyl)-4,6-dihydropyrimido[4,5-d]pyridazine-2,5-(1H,3H)-dione
  参考文献：
  名称：

  Synthesis of 4-Aryl-4,6-dihydropyrimido[4,5-d]pyridazine-2,5(1H,3H)-diones fromBiginelliCompounds

  摘要：

  AbstractBiginelli compounds 1 were first brominated at MeC(6) with 2,4,4,6‐tetrabromocyclohex‐2,5‐dien‐1‐one to give Br2CHC(6) derivatives 2. The hydrolysis of the 6‐(dibromomethyl) group of 2c to give the 6‐formyl derivative 3c in the presence of an expensive Ag salt followed by reaction with N2H4⋅H2O yielded tetrahydropyrimido[4,5‐d]pyridazine‐2,5(1H,3H)‐dione (4c; Scheme 1). However, treatment of the 6‐(dibromomethyl) derivatives 2 directly with N2H4⋅H2O led to the fused heterocycles 4 in better overall yield (Schemes 1 and 2; Table).

  DOI：

  10.1002/hlca.201200109
• 作为产物：
  描述：

  4-(4-溴苯基)-6-甲基-2-氧代-3,4-二氢-1H-嘧啶-5-羧酸乙酯 在 四溴环己二烯-1-酮 、 silver(I) acetate 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 0.33h， 生成 ethyl 4-(4-bromophenyl)-6-formyl-1,2,3,4-tetrahydro-2-oxopyrimidine-5-carboxylate
  参考文献：
  名称：

  Synthesis of 4-Aryl-4,6-dihydropyrimido[4,5-d]pyridazine-2,5(1H,3H)-diones fromBiginelliCompounds

  摘要：

  AbstractBiginelli compounds 1 were first brominated at MeC(6) with 2,4,4,6‐tetrabromocyclohex‐2,5‐dien‐1‐one to give Br2CHC(6) derivatives 2. The hydrolysis of the 6‐(dibromomethyl) group of 2c to give the 6‐formyl derivative 3c in the presence of an expensive Ag salt followed by reaction with N2H4⋅H2O yielded tetrahydropyrimido[4,5‐d]pyridazine‐2,5(1H,3H)‐dione (4c; Scheme 1). However, treatment of the 6‐(dibromomethyl) derivatives 2 directly with N2H4⋅H2O led to the fused heterocycles 4 in better overall yield (Schemes 1 and 2; Table).

  DOI：

  10.1002/hlca.201200109