(2R,5S)-5-(4-acetoxy-2-butynyl)-5-(3-butenyl)-2,5-dihydro-3,6-dimethoxy-n-2-isopropylpyrazine | 194287-27-9

• 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-(4-acetoxy-2-butynyl)-5-(3-butenyl)-2,5-dihydro-3,6-dimethoxy-n-2-isopropylpyrazine
• 英文别名: 4-[(2R,5S)-5-but-3-enyl-3,6-dimethoxy-2-propan-2-yl-2H-pyrazin-5-yl]but-2-ynyl acetate
• CAS: 194287-27-9
• 化学式: C₁₉H₂₈N₂O₄
• 分子量: 348.442
• InChiKey: FOISYTZECVLDKI-APWZRJJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  69.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,5S)-5-(4-acetoxy-2-butynyl)-5-(3-butenyl)-2,5-dihydro-3,6-dimethoxy-n-2-isopropylpyrazine 在 Grubbs catalyst first generation 作用下， 以 苯 为溶剂， 反应 14.0h， 以71%的产率得到Acetic acid 2-((3R,6S)-3-isopropyl-2,5-dimethoxy-1,4-diaza-spiro[5.5]undeca-1,4,8-trien-8-yl)-allyl ester
  参考文献：
  名称：

  Ruthenium-catalyzed enyne metathesis in stereoselective preparation of cyclic 1-amino-1-carboxylic acids

  摘要：

  Stereoselective syntheses of alpha-amino acids are described. The alpha-carbon of the amino acid is incorporated into a five- or six-membered ring which is a conjugated diene with one exocyclic double bond. Enynes were intermediates for the metathesis cyclization reaction effected by ruthenium(II)-catalysis. The enyne substrates were available in stereochemically pure form by stepwise alkylations of the chiral auxiliary (R)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine with bromo-alkenes and -alkynes. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00671-6
• 作为产物：
  描述：

  (2R,5S)-5-(3-butenyl)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-(2-propynyl)pyrazine 在 4-二甲氨基吡啶 、 正丁基锂 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (2R,5S)-5-(4-acetoxy-2-butynyl)-5-(3-butenyl)-2,5-dihydro-3,6-dimethoxy-n-2-isopropylpyrazine
  参考文献：
  名称：

  Ruthenium-catalyzed enyne metathesis in stereoselective preparation of cyclic 1-amino-1-carboxylic acids

  摘要：

  Stereoselective syntheses of alpha-amino acids are described. The alpha-carbon of the amino acid is incorporated into a five- or six-membered ring which is a conjugated diene with one exocyclic double bond. Enynes were intermediates for the metathesis cyclization reaction effected by ruthenium(II)-catalysis. The enyne substrates were available in stereochemically pure form by stepwise alkylations of the chiral auxiliary (R)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine with bromo-alkenes and -alkynes. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00671-6

文献信息

• Ruthenium-catalyzed enyne metathesis in stereoselective preparation of cyclic 1-amino-1-carboxylic acids
  作者：Kristin Hammer、Kjell Undheim

  DOI：10.1016/s0040-4020(97)00671-6

  日期：1997.7

  Stereoselective syntheses of alpha-amino acids are described. The alpha-carbon of the amino acid is incorporated into a five- or six-membered ring which is a conjugated diene with one exocyclic double bond. Enynes were intermediates for the metathesis cyclization reaction effected by ruthenium(II)-catalysis. The enyne substrates were available in stereochemically pure form by stepwise alkylations of the chiral auxiliary (R)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine with bromo-alkenes and -alkynes. (C) 1997 Elsevier Science Ltd.