1-benzoyl-2(S)-tert-butyl-3-methyl-2,3-dihydro-4(1H)-pyrimidin-4-one | 143870-67-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-benzoyl-2(S)-tert-butyl-3-methyl-2,3-dihydro-4(1H)-pyrimidin-4-one
• 英文别名: 1-benzoyl-2(S)-tert-butyl-3-methyl-2,3-dihydro-4(H)-pyrimidin-4-one；(2S)-1-benzoyl-2-tert-butyl-3-methyl-2H-pyrimidin-4-one
• CAS: 143870-67-1
• 化学式: C₁₆H₂₀N₂O₂
• 分子量: 272.347
• InChiKey: HCOPNXVDPCYTSD-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzoyl-2(S)-tert-butyl-3-methyl-2,3-dihydro-4(1H)-pyrimidin-4-one 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 乙酸乙酯 为溶剂， 45.0 ℃ 、7.6 MPa 条件下， 反应 24.0h， 以98%的产率得到1-benzoyl-2(S)-tert-butyl-3-methylperhydropyrimidin-4-one
  参考文献：
  名称：

  β-氨基酸的对映选择性合成。7.由1-苯甲酰基-2（S）-叔丁基-3-甲基全氢嘧啶-4-酮的对映体纯α-取代的β-氨基酸的制备。1,2

  摘要：

  廉价的天然α-氨基酸L-天冬酰胺被有效地转化为对映体纯态的（R）-或（S）-α-烷基化的β-氨基酸。该方案中的关键中间体是对映体N，N-乙缩醛嘧啶酮（S）-1 ，一种掩盖的β-丙氨酸手性衍生物。

  DOI：

  10.1016/0957-4166(96)00278-9
• 作为产物：
  描述：

  cis-2-tert-butyl-6(S)-potassium carboxylate-perhydropyrimidin-4-one 在 lead(IV) acetate 、 正丁基锂 、 copper diacetate 、 碳酸氢钠 作用下， 生成 1-benzoyl-2(S)-tert-butyl-3-methyl-2,3-dihydro-4(1H)-pyrimidin-4-one
  参考文献：
  名称：

  Preparation and assignment of configuration of 1-benzoyl- (2S)-tert-butyl-3-methyl-perhydropyrimidin-4-one. Useful starting material for the enantioselective synthesis of α-substituted β-amino acids

  摘要：

  (S) -Asparagine, an inexpensive beta-amino acid was converted into the title heterocycle (+)-1 in very good overall yield. The highly selective trans methylation of (+)-1-Li, and the hydrolysis of the resulting adduct afforded (R)-alpha-methyl-beta-alanine, allowing the assignment of the (S) configuration in (+)-1.

  DOI：

  10.1016/s0957-4166(00)80511-x

文献信息

• Alternative procedure for the synthesis of enantiopure 1-benzoyl-2(S)-tert-butyl-3-methylperhydropyrimidin-4-one, a useful starting material for the enantioselective synthesis of α-substituted β-amino acids
  作者：Martı́n A. Iglesias-Arteaga、Elena Castellanos、Eusebio Juaristi

  DOI：10.1016/s0957-4166(03)00048-x

  日期：2003.3

  The title heterocycle is prepared in enantiomerically pure form and in 46-50% overall yield from (S)-asparagine, a readily available starting material. The synthetic route described in this report represents a major improvement over the original procedure (Tetrahedron: Asymmetry 1991, 3, 723), that afforded a 24-32% overall yield. Furthermore, the use of toxic reagents such as Pb(OAc)(4) and dimethyl sulfate is avoided in the present protocol. (C) 2003 Published by Elsevier Science Ltd.
• Enantioselective synthesis of β-amino acids. 7. Preparation of enantiopure α-substituted β-amino acids from 1-benzoyl-2(S)-tert-butyl-3-methylperhydropyrimidin-4-one.1,2
  作者：Eusebio Juaristi、Delia Quintana、Margarita Balderas、Enrique García-Pérez

  DOI：10.1016/0957-4166(96)00278-9

  日期：1996.8

  Inexpensive natural α-amino acid L-asparagine was efficiently converted to either (R)- or (S)-α-alkylated β-amino acids in enantiomerically pure state. The key intermediate in this protocol is the enantiopure N,N-acetal pyrimidinone (S)-1, a masked chiral derivative of β-alanine.

  廉价的天然α-氨基酸L-天冬酰胺被有效地转化为对映体纯态的（R）-或（S）-α-烷基化的β-氨基酸。该方案中的关键中间体是对映体N，N-乙缩醛嘧啶酮（S）-1 ，一种掩盖的β-丙氨酸手性衍生物。
• Preparation and assignment of configuration of 1-benzoyl- (2S)-tert-butyl-3-methyl-perhydropyrimidin-4-one. Useful starting material for the enantioselective synthesis of α-substituted β-amino acids
  作者：Eusebio Juaristi、Delia Quintana

  DOI：10.1016/s0957-4166(00)80511-x

  日期：1992.6

  (S) -Asparagine, an inexpensive beta-amino acid was converted into the title heterocycle (+)-1 in very good overall yield. The highly selective trans methylation of (+)-1-Li, and the hydrolysis of the resulting adduct afforded (R)-alpha-methyl-beta-alanine, allowing the assignment of the (S) configuration in (+)-1.