(3R,6S)-10-ethenyl-2,5-dimethoxy-3-propan-2-yl-1,4-diazaspiro[5.5]undeca-1,4,9-triene | 194287-34-8

• 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: (3R,6S)-10-ethenyl-2,5-dimethoxy-3-propan-2-yl-1,4-diazaspiro[5.5]undeca-1,4,9-triene
• CAS: 194287-34-8
• 化学式: C₁₆H₂₄N₂O₂
• 分子量: 276.379
• InChiKey: QTMBKAXOFZXJKE-CJNGLKHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  43.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,6S)-10-ethenyl-2,5-dimethoxy-3-propan-2-yl-1,4-diazaspiro[5.5]undeca-1,4,9-triene 在 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 72.0h， 以83%的产率得到methyl (1S)-1-amino-3-ethenylcyclohex-3-ene-1-carboxylate
  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 Grubbs catalyst first generation 作用下， 以 苯 为溶剂， 反应 14.0h， 以81%的产率得到(3R,6S)-10-ethenyl-2,5-dimethoxy-3-propan-2-yl-1,4-diazaspiro[5.5]undeca-1,4,9-triene
  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.