(1R,5R)-(+)-2,6-diethyl-4,8-dimethylglycoluril

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (1R,5R)-(+)-2,6-diethyl-4,8-dimethylglycoluril
• 英文别名: (+)-(1R,5R)-2,6-diethyl-4,8-dimethyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione；(3aR,6aR)-3,6-diethyl-1,4-dimethyl-3a,6a-dihydroimidazo[4,5-d]imidazole-2,5-dione
• 化学式: C₁₀H₁₈N₄O₂
• 分子量: 226.279
• InChiKey: OYMJBLPBWFQYBE-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  47.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,5R)-(+)-2,6-diethyl-4,8-dimethylglycoluril 、 (R)-1,1'-Bi-2-naphthol 在 水 作用下， 以 乙酸乙酯 为溶剂， 生成 、
  参考文献：
  名称：

  The chiral drug Albicar: resolution of its racemate via complexation with BINOL

  摘要：

  通过(R)-(+)-BINOL-(+)-1-H2O 复合物和(R)-(+)-(S)-BINOL-(+)-1-H2O 复合物制备出了标题药物（2,6-二乙基-4,8-二甲基甘氨酰脲；1）的两种对映体，其外消旋体的收率分别为 59%（（+）-1）和 43%（（-）-1）。通过对(R)-(+)-BINOL-(+)-1-H2O 复合物进行 XRD 研究，确定了(1R,5R)-(+)-1 的绝对构型。

  DOI：

  10.1039/b9nj00701f
• 作为产物：
  描述：

  2,6-diethyl-2,4,6,8-tetraazabicyclo<3.3.0>octene-3,7-dione 在 氢氧化钾 作用下， 以 水 为溶剂， 反应 3.0h， 生成 (1R,5R)-(+)-2,6-diethyl-4,8-dimethylglycoluril
  参考文献：
  名称：

  Chiral drugs via the spontaneous resolution

  摘要：

  The psychotropically active drug Albicar 1 has been prepared for the first time in both enantiomeric ally pure forms starting from the (+)-2 and (-)-2 precursors obtained by spontaneous resolution; the crystal structures of (-)-1 and (+/-)-1 have been solved by X-ray diffraction study.

  DOI：

  10.1070/mc2002v012n01abeh001521

文献信息

• Preparative synthesis and pharmacological activity of Albicar racemate and enantiomers
  作者：Lada V. Anikina、Yuri B. Vikharev、Vladimir V. Baranov、Oleg R. Malyshev、Angelina N. Kravchenko

  DOI：10.1016/j.mencom.2018.05.030

  日期：2018.5

  Racemic Albicar (2,6-diethyl-4,8-dimethylglycoluril) has been synthesized and resolved into enantiomers on a preparative scale by chiral HPLC. A comparison of the pharmacological effects of these compounds has been performed for the first time. It has been demonstrated that the (−)-(1S,5S)-enantiomer exerts a stimulating effect on the central nervous system due to activation of the serotonergic system

  外消旋Albicar（2,6-diethyl-4,8-​​methylglycoluril）已合成，并通过手性HPLC拆分成对映异构体。这些化合物的药理作用比较是第一次。已经证明，（-）-（1S，5S）-对映异构体由于血清素能系统的激活而对中枢神经系统产生刺激作用，因为它增强了5-羟色氨酸（5-羟色胺前体）的作用，而血清素受体拮抗剂阻断其活性。（+）-（1R，5R）-对映异构体显示出抑制作用。
• Chiral drugs via the spontaneous resolution
  作者：Remir G. Kostyanovsky、Gul’nara K. Kadorkina、Konstantin A. Lyssenko、Vladimir Yu. Torbeev、Angelina N. Kravchenko、Oleg V. Lebedev、Gennadii V. Grintselev-Knyazev、Vasily R. Kostyanovsky

  DOI：10.1070/mc2002v012n01abeh001521

  日期：2002.1

  The psychotropically active drug Albicar 1 has been prepared for the first time in both enantiomeric ally pure forms starting from the (+)-2 and (-)-2 precursors obtained by spontaneous resolution; the crystal structures of (-)-1 and (+/-)-1 have been solved by X-ray diffraction study.
• The chiral drug Albicar: resolution of its racemate via complexation with BINOL
  作者：Denis A. Lenev、Konstantin A. Lyssenko、Remir G. Kostyanovsky

  DOI：10.1039/b9nj00701f

  日期：——

  Both enantiomers of the title drug (2,6-diethyl-4,8-dimethylglycoluril; 1) were prepared from their complexes with (R)- and (S)-BINOL in 59% ((+)-1) and 43% ((−)-1) yield from its racemate. The absolute configuration of (1R,5R)-(+)-1 was determined by an XRD study of the (R)-(+)-BINOL-(+)-1·H2O complex.

  通过(R)-(+)-BINOL-(+)-1-H2O 复合物和(R)-(+)-(S)-BINOL-(+)-1-H2O 复合物制备出了标题药物（2,6-二乙基-4,8-二甲基甘氨酰脲；1）的两种对映体，其外消旋体的收率分别为 59%（（+）-1）和 43%（（-）-1）。通过对(R)-(+)-BINOL-(+)-1-H2O 复合物进行 XRD 研究，确定了(1R,5R)-(+)-1 的绝对构型。