(2S,5S)-bis-(2-propenyl)-3,6-(diethoxy)-2,5-dihydropyrazine | 158547-80-9

• 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: (2S,5S)-bis-(2-propenyl)-3,6-(diethoxy)-2,5-dihydropyrazine
• CAS: 158547-80-9
• 化学式: C₁₄H₂₂N₂O₂
• 分子量: 250.341
• InChiKey: BSDJSUUUEROOTD-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  43.18
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,5S)-bis-(2-propenyl)-3,6-(diethoxy)-2,5-dihydropyrazine 在 盐酸 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以90%的产率得到(S)-(-)-2-氨基-4-戊烯酸
  参考文献：
  名称：

  Synthesis of (3R,6R)- and (3S,6S)-3,6-dialkylpiperazin-2,5-dione derivatives as useful intermediates to both (R) and (S) α-aminoacids

  摘要：

  The alkylation of 2 leads to a diastereomeric mixture where 4 is generally present in greater amounts than 3. The successive alkylation of 4 affords exclusively the cis derivative 7, while a cis/trans mixture is obtained from isomer 3. In alkaline solution, the trans isomer 6 suffers a total conversion into a 1:1 mixture of the cis isomers 5 and 7 easily separated by silica gel chromatography. The configurations of the introduced stereogenic centers at C-3 and C-6 have been assigned on the basis of H-1-NMR spectroscopic data. Cleavage of heterocyclic ring of 5 and 7 leads to the corresponding (R)- and (S)-alpha-aminoacids respectively. Therefore, the substrate 2 appears a very useful chiral template to synthetize enantiomerically pure alpha-amino acids.

  DOI：

  10.1016/s0957-4166(00)86217-5
• 作为产物：
  描述：

  (3S,6S)-1,4-N,N-((S)-1-phenethyl)-3,6-bis-(2-propenyl)piperazine-2,5-dione 在 氨 、 lithium 、 叔丁醇 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.08h， 生成 (2S,5S)-bis-(2-propenyl)-3,6-(diethoxy)-2,5-dihydropyrazine
  参考文献：
  名称：

  Synthesis of (3R,6R)- and (3S,6S)-3,6-dialkylpiperazin-2,5-dione derivatives as useful intermediates to both (R) and (S) α-aminoacids

  摘要：

  The alkylation of 2 leads to a diastereomeric mixture where 4 is generally present in greater amounts than 3. The successive alkylation of 4 affords exclusively the cis derivative 7, while a cis/trans mixture is obtained from isomer 3. In alkaline solution, the trans isomer 6 suffers a total conversion into a 1:1 mixture of the cis isomers 5 and 7 easily separated by silica gel chromatography. The configurations of the introduced stereogenic centers at C-3 and C-6 have been assigned on the basis of H-1-NMR spectroscopic data. Cleavage of heterocyclic ring of 5 and 7 leads to the corresponding (R)- and (S)-alpha-aminoacids respectively. Therefore, the substrate 2 appears a very useful chiral template to synthetize enantiomerically pure alpha-amino acids.

  DOI：

  10.1016/s0957-4166(00)86217-5