(2S,5R,1'R,1''R,2''R)-5-isopropyl-3,6-dimethoxy-2-[1'-(2''-methoxymethoxy-cyclopropyl)-ethyl]-2,5-dihydropyrazine | 835629-47-5

• 分子结构分类: 有机化合物
• 英文名称: (2S,5R,1'R,1''R,2''R)-5-isopropyl-3,6-dimethoxy-2-[1'-(2''-methoxymethoxy-cyclopropyl)-ethyl]-2,5-dihydropyrazine
• 英文别名: (2S,5R)-3,6-dimethoxy-2-[(1R)-1-[(1R,2R)-2-(methoxymethoxy)cyclopropyl]ethyl]-5-propan-2-yl-2,5-dihydropyrazine
• CAS: 835629-47-5
• 化学式: C₁₆H₂₈N₂O₄
• 分子量: 312.409
• InChiKey: XCYCUHBENACMKG-KSTCHIGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.13
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  61.64
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2S,5R,1'R,1''R,2''R)-5-isopropyl-3,6-dimethoxy-2-[1'-(2''-methoxymethoxy-cyclopropyl)-ethyl]-2,5-dihydropyrazine 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以75%的产率得到(2S,3R,1'R,2'R)-2-amino-3-(2'-methoxymethoxy-cyclopropyl)-butyric acid methyl ester
  参考文献：
  名称：

  Chemistry of vinyl sulfones. Approach to novel conformationally restricted analogues of glutamic acid

  摘要：

  A totally different approach to conformationally restricted glutamic acid analogues is described, in which one of the acid functions is replaced by a cyclopropanol. The reactivity of cyclopropanol vinyl sulfones toward addition of lithiated Schollkopf bislactim ether provides a facile synthesis of a-amino acid diastereoisomers. Conformational analysis of these analogues, incorporating solvation effects, and docking to a glutamate receptor model, are used to show the relevance of the conformational restrictions employed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.10.072
• 作为产物：
  描述：

  (2S,5R,1'R,1''R,2''R)-2-{2'-benzenesulfonyl-1'-[2''-(tert-butyldimethylsilanyloxy)-cyclopropyl]-ethyl}-5-isopropyl-3,6-dimethoxy-2,5-dihydro-pyrazine 在 甲醇 、 sodium amalgam 、 四丁基氟化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 (2S,5R,1'R,1''R,2''R)-5-isopropyl-3,6-dimethoxy-2-[1'-(2''-methoxymethoxy-cyclopropyl)-ethyl]-2,5-dihydropyrazine
  参考文献：
  名称：

  Chemistry of vinyl sulfones. Approach to novel conformationally restricted analogues of glutamic acid

  摘要：

  A totally different approach to conformationally restricted glutamic acid analogues is described, in which one of the acid functions is replaced by a cyclopropanol. The reactivity of cyclopropanol vinyl sulfones toward addition of lithiated Schollkopf bislactim ether provides a facile synthesis of a-amino acid diastereoisomers. Conformational analysis of these analogues, incorporating solvation effects, and docking to a glutamate receptor model, are used to show the relevance of the conformational restrictions employed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.10.072