4-Hydroxy-6-(4-methoxy-phenyl)-4-methyl-2-oxo-hexahydro-pyrimidine-5-carboxylic acid ethyl ester | 1033553-70-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-Hydroxy-6-(4-methoxy-phenyl)-4-methyl-2-oxo-hexahydro-pyrimidine-5-carboxylic acid ethyl ester
• CAS: 1033553-70-6
• 化学式: C₁₅H₂₀N₂O₅
• 分子量: 308.334
• InChiKey: ZQTKOQLHTFPEQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.94
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  96.89
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-Hydroxy-6-(4-methoxy-phenyl)-4-methyl-2-oxo-hexahydro-pyrimidine-5-carboxylic acid ethyl ester 在 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 生成 ethyl 4-(4-methoxyphenyl)-6-methyl-1,2,3,4-tetrahydropyrimidin-2-one-5-carboxylate
  参考文献：
  名称：

  A new approach to the synthesis of Biginelli compounds

  摘要：

  A new synthesis of 4-aryl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid esters is based on the reactions of alpha-tosyl-substituted phenyl carbamates with the enolates of beta-oxoesters followed by treatment with ammonia and dehydration of the resulting 4-hydroxyhexahydropyrimidin-2-ones.

  DOI：

  10.1070/mc2005v015n02abeh002022
• 作为产物：
  描述：

  phenyl [(p-metoxyphenyl)(tosyl)methyl]carbamate 在 ammonium hydroxide 、 sodium hydride 作用下， 以 乙腈 为溶剂， 反应 6.0h， 生成 4-Hydroxy-6-(4-methoxy-phenyl)-4-methyl-2-oxo-hexahydro-pyrimidine-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  A new approach to the synthesis of Biginelli compounds

  摘要：

  A new synthesis of 4-aryl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid esters is based on the reactions of alpha-tosyl-substituted phenyl carbamates with the enolates of beta-oxoesters followed by treatment with ammonia and dehydration of the resulting 4-hydroxyhexahydropyrimidin-2-ones.

  DOI：

  10.1070/mc2005v015n02abeh002022

文献信息

• Towards Enzyme-like, Sustainable Catalysis: Switchable, Highly Efficient Asymmetric Synthesis of Enantiopure Biginelli Dihydropyrimidinones or Hexahydropyrimidinones
  作者：V. J. Lillo、J. M. Saá

  DOI：10.1002/chem.201604433

  日期：2016.11.21

  Organocatalysts displaying a network of cooperative hydrogen bonds (NCHB) have been employed in an enzyme‐like manner for a direct, switchable synthesis of enantiopure hexahydropyrimidinones (HHPMs) or dihydropyrimidinones (DHPMs), which starts at a common, easily accessible α‐ureidosulfone stage. The NCHB organocatalyst exploits all its potential as a pure hydrogen‐bond biomimetic catalyst even in

  具有协同氢键网络（NCHB）的有机催化剂已以类似酶的方式用于直接，可转换的对映纯六氢嘧啶酮（HHPM）或二氢嘧啶酮（DHPM）的合成，其起始于常见的易于获得的α-脲基砜阶段。NCHB有机催化剂即使在存在有机碱的情况下，也可以发挥其作为纯氢键仿生催化剂的全部潜力。这种单锅，非对映和对映选择性合成方法已被证明是可靠，可扩展，高效且对环境无害的。首次报道了一种直接，真正实用的对映纯HHPMs。