(2R,5S)-5-(3-butenyl)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-(1-oxo-2-propenyl)pyrazine | 210431-43-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 英文名称: (2R,5S)-5-(3-butenyl)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-(1-oxo-2-propenyl)pyrazine
• 英文别名: 1-[(2R,5R)-5-but-3-enyl-3,6-dimethoxy-2-propan-2-yl-2H-pyrazin-5-yl]prop-2-en-1-one
• CAS: 210431-43-9
• 化学式: C₁₆H₂₄N₂O₃
• 分子量: 292.378
• InChiKey: GWXIIDLAWQJVKL-CJNGLKHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  60.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,5S)-5-(3-butenyl)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-(1-oxo-2-propenyl)pyrazine 在 copper(l) iodide 、 Grubbs catalyst first generation 作用下， 以 乙醚 、 1,2-二氯乙烷 为溶剂， 反应 4.75h， 生成 (2R,5S,4'S)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine-5-spiro(4-methylcyclohexan-2-one)
  参考文献：
  名称：

  SYNTHESIS OF CYCLIC CONSTRAINED β-OXO-SUBSTITUTED α-AMINO ACIDS

  摘要：

  Ru(II)-catalyzed RCM reaction with a 5,5-diene of (2R)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine provided a spiroannulated cyclohexenone as substrate for conjugate additions of organocuprates. Acid hydrolysis gave beta-oxo-substituted alpha-amino acids. Assignments of configurations are based on single crystal X-ray analyses.

  DOI：

  10.1081/scc-120002404
• 作为产物：
  描述：

  (2R,5S,1'S/R)-5-(3-butenyl)-2,5-dihydro-3,6-dimethoxy-5-(1-hydroxy-2-propenyl)-2-isopropylpyrazine 在 草酰氯 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 以73%的产率得到(2R,5S)-5-(3-butenyl)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-(1-oxo-2-propenyl)pyrazine
  参考文献：
  名称：

  SYNTHESIS OF CYCLIC CONSTRAINED β-OXO-SUBSTITUTED α-AMINO ACIDS

  摘要：

  Ru(II)-catalyzed RCM reaction with a 5,5-diene of (2R)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine provided a spiroannulated cyclohexenone as substrate for conjugate additions of organocuprates. Acid hydrolysis gave beta-oxo-substituted alpha-amino acids. Assignments of configurations are based on single crystal X-ray analyses.

  DOI：

  10.1081/scc-120002404

文献信息

• Ru(II)-catalyzed RCM reactions with electrophilic diene substrates
  作者：Sonata Krikstolaitytè、Kristin Hammer、Kjell Undheim

  DOI：10.1016/s0040-4039(98)01651-7

  日期：1998.10

  Electrophilic dienes from alpha,beta-unsaturated ketones readily undergo the Ru(II)-benzylidene initiated RCM reaction. Cyclohexenone spirane formation was faster than cycloheptenone spirane formation. The products were pure stereoisomers. The products after hydrolysis were alpha,beta-unsaturated axo derivatives of cyclic alpha-amino acids. (C) 1998 Elsevier Science Ltd. All rights reserved.
• SYNTHESIS OF CYCLIC CONSTRAINED β-OXO-SUBSTITUTED α-AMINO ACIDS
  作者：Sonata Krikstolaityté、Kristin Hammer、Christian Rømming、Kjell Undheim

  DOI：10.1081/scc-120002404

  日期：2002.1.1

  Ru(II)-catalyzed RCM reaction with a 5,5-diene of (2R)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine provided a spiroannulated cyclohexenone as substrate for conjugate additions of organocuprates. Acid hydrolysis gave beta-oxo-substituted alpha-amino acids. Assignments of configurations are based on single crystal X-ray analyses.