5-ethoxycarbonyl-3,6-dimethyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one | 123043-98-1

• 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: 5-ethoxycarbonyl-3,6-dimethyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one
• 英文别名: 3,6-dimethyl-2-oxo-4-phenyl-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester；3,6-Dimethyl-2-oxo-4-phenyl-1,2,3,4-tetrahydro-pyrimidin-5-carbonsaeure-aethylester；Ethyl 3,6-dimethyl-2-oxo-4-phenyl-1,4-dihydropyrimidine-5-carboxylate
• CAS: 123043-98-1
• 化学式: C₁₅H₁₈N₂O₃
• 分子量: 274.32
• InChiKey: GYBNGGVHTBHTJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-ethoxycarbonyl-3,6-dimethyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one 生成 (S)-3,6-Dimethyl-2-oxo-4-phenyl-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  Separation of enantiomers of 4-aryldihydropyrimidines by direct enantioselective HPLC. A critical comparison of chiral stationary phases

  摘要：

  The separation of the enantiomers of 29 racemic 4-aryldihydropyrimidine-5-carboxylates (DHPMs), aza-analogs of nifedipine-type dihydropyridine calcium channel modulators, was evaluated in direct enantioselective HPLC, employing the following commercially available chiral stationary phases (CSPs): Chiralcel OD-H, ChiraDex, Chirobiotic V and T, and Whelk-O1. In addition, a 1,2-diphenyl-1,2-diaminoethane based CSP and two quinine carbamate based chiral ion exchangers were also employed. For all 29 DHPMs separation of individual enantiomers could be achieved with at least one CSP with alpha-values ranging from 1.10 to 8.67. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00214-0
• 作为产物：
  描述：

  6-甲基-4-苯基-2-硫代-1,2,3,4-四氢嘧啶-5-羧酸乙酯 在 水 、 potassium carbonate 、 溶剂黄146 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 5-ethoxycarbonyl-3,6-dimethyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one
  参考文献：
  名称：

  Kappe, Christian Oliver; Roschger, Peter, Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 55 - 64

  摘要：

  DOI：

文献信息

• Metalation of Biginelli Compounds. A General Unprecedented Route to C-6 Functionalized 4-Aryl-3,4-dihydropyrimidinones
  作者：Kamaljit Singh、Sukhdeep Singh、Aman Mahajan

  DOI：10.1021/jo050675q

  日期：2005.7.1

  4-Aryl-6-methyl-3,4-dihydro-2(1H)-pyrimidinone esters (DHPMs) readily undergo metalation at the C-6 methyl (vinylogous ester) position on treatment with lithium diisopropylamide at −10 °C. The resulting anion intermediates can be treated with electrophilic reagents to afford functionalized DHPMs that have been chemically elaborated mainly at the C-6 position. Di- and trianion formation is also possible

  在-10°C下用二异丙基氨基锂处理时，4-芳基-6-甲基-3,4-二氢-2（1 H）-嘧啶酮酯（DHPM）易于在C-6甲基（乙烯基酯）位置发生金属化。可以用亲电试剂处理所得的阴离子中间体，以提供功能化的DHPM，该功能化的DHPM主要在C-6位置进行了化学修饰。当用过量当量的碱进行反应时，在乙烯基的甲基和NH位置也可能形成二阴离子和三阴离子。
• Researches on Pyrimidines. CXXXIII. Some Reactions and Derivatives of 2-Keto-4-phenyl-5-carbethoxy-6-methyl-1,2,3,4-tetrahydropyrimidine
  作者：Karl Folkers、T. B. Johnson

  DOI：10.1021/ja01334a043

  日期：1933.7
• KAPPE, CHRISTIAN OLIVER;ROSCHGER, PETER, J. HETEROCYCL. CHEM., 26,(1989) N, C. 55-64
  作者：KAPPE, CHRISTIAN OLIVER、ROSCHGER, PETER

  DOI：——

  日期：——
• Separation of enantiomers of 4-aryldihydropyrimidines by direct enantioselective HPLC. A critical comparison of chiral stationary phases
  作者：Oliver P. Kleidernigg、C.Oliver Kappe

  DOI：10.1016/s0957-4166(97)00214-0

  日期：1997.6

  The separation of the enantiomers of 29 racemic 4-aryldihydropyrimidine-5-carboxylates (DHPMs), aza-analogs of nifedipine-type dihydropyridine calcium channel modulators, was evaluated in direct enantioselective HPLC, employing the following commercially available chiral stationary phases (CSPs): Chiralcel OD-H, ChiraDex, Chirobiotic V and T, and Whelk-O1. In addition, a 1,2-diphenyl-1,2-diaminoethane based CSP and two quinine carbamate based chiral ion exchangers were also employed. For all 29 DHPMs separation of individual enantiomers could be achieved with at least one CSP with alpha-values ranging from 1.10 to 8.67. (C) 1997 Elsevier Science Ltd.
• Kappe, Christian Oliver; Roschger, Peter, Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 55 - 64
  作者：Kappe, Christian Oliver、Roschger, Peter

  DOI：——

  日期：——