阿维霉素 | 51004-33-2

• 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: 阿维霉素
• 英文名称: (R)-5-ethoxycarbonyl-1,6-dimethyl-4-phen yl-3,4-dihydropyrimidin-2(1H)-one
• 英文别名: ethyl (4R)-1,6-dimethyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate；Ethyl(4r)-1,6-dimethyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate；ethyl (6R)-3,4-dimethyl-2-oxo-6-phenyl-1,6-dihydropyrimidine-5-carboxylate
• CAS: 51004-33-2
• 化学式: C₁₅H₁₈N₂O₃
• mdl: MFCD00205132
• 分子量: 274.32
• InChiKey: GRZXAQPDZOWXCI-CYBMUJFWSA-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

• 作为产物：
  描述：

  ethyl 1,6-dimethyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate 生成 阿维霉素
  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

文献信息

• The enantiomeric recognition of dihydropyrimidonic compounds by chiral selectors derived from 4- or 2-chloro-3,5-dinitrobenzoic acid
  作者：Ivana Gazić、Darko Kontrec、Andreja Lesac、Vladimir Vinković

  DOI：10.1016/j.tetasy.2005.01.042

  日期：2005.3

  Six new chiral packing materials for high performance liquid chromatography have been prepared from chiral selectors consisting of 4- or 2-chloro-3,5-dinitrobenzoic acid, L-alanine and different pi-donor aromatic units. Comparative tests of these newly prepared CSPs on separation efficiency for 13 racemic dihydropyrimidonic (DHPM) analytes have revealed the strong contribution of the pi-acceptor branching unit, as well as the important influence of the structure of the terminal pi-donor unit. The role of the terminal aromatic group is primarily to increase the rigidity of the selector structure. Comparisons of the data revealed that selectors bound on the silica gel could be preorganized during the process of chiral recognition, resulting in the similar enantioseparation properties for DHPM analytes on both types of CSPs. However, some other compounds, such as amino alcohol beta-agonists, exhibit very different enantioseparations. (C) 2005 Elsevier Ltd. All rights reserved.
• Chemical resolution of enantiomers of 3,4-dihydropyrimidin-2(1H)-ones using chiral auxiliary approach
  作者：Kamaljit Singh、Kawaljit Singh、Hardeep Kaur

  DOI：10.1016/j.tet.2012.05.073

  日期：2012.8

  Inherently racemic DHPMs have been resolved using chemical resolution methodology by appending enantiopure chiral auxiliary at N-1 or N-3 position of the DHPMs, leading to the formation of both diastereomers, which were separated chromatographically to obtain both enantiomers (ee upto 99.9%) of DHPMs, after removal of the auxiliary. Absolute configuration of the enantiomers has been assigned. (C) 2012 Elsevier Ltd. All rights reserved.
• 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.