2,5-Bisethoxy-3-ethoxycarbonyl-6-isopropyl-3,6-dihydropyrazin | 219657-71-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,5-Bisethoxy-3-ethoxycarbonyl-6-isopropyl-3,6-dihydropyrazin
• 英文别名: ethyl (5S)-3,6-diethoxy-5-propan-2-yl-2,5-dihydropyrazine-2-carboxylate
• CAS: 219657-71-3
• 化学式: C₁₄H₂₄N₂O₄
• 分子量: 284.356
• InChiKey: ZMTZCKCEAFOBFZ-VUWPPUDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 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：

  2,5-Bisethoxy-3-ethoxycarbonyl-6-isopropyl-3,6-dihydropyrazin 在 2,6-二甲基吡啶 、 二异丁基氢化铝 、 三乙胺 、 magnesium bromide 作用下， 以 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Tin- or magnesium-mediated diastereoselective aldol-type reactions for the asymmetric synthesis of α-substituted serines

  摘要：

  Diastereoselective aldol-type reactions of ethyl (5S)-3,6-diethoxy-2,5-dihydro-5-isopropyl-2-pyrazine-carboxylate (5S)-3 with achiral aldehydes 8a-d was investigated by using Sn(OSO2CF3)(2)-N-ethylpiperizine and MgBr2-triethylamine. The reaction with Sn(II) between (5S)-3 and aliphatic aldehydes 8a,b proved to be quite different from that with Mg(II). On the other hand, Sn(II)- or Mg(II)-mediated aldol-type reactions of (5S)-3 with benzaldehyde Sc and 3-methyl-2-butenal 8d each afforded the same diastereomer as the major product. These aldol products were each converted to the corresponding alpha-substituted serines 6 and 7 as enantiomerically pure compounds. (C) 1998 Elsevier Science Ltd. AII rights reserved.

  DOI：

  10.1016/s0957-4166(98)00371-1
• 作为产物：
  描述：

  Cbo-D,L-valyl-aminomalonsaeurediethylester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 42.0h， 生成 2,5-Bisethoxy-3-ethoxycarbonyl-6-isopropyl-3,6-dihydropyrazin
  参考文献：
  名称：

  6-Alkyl-2,5-bisethoxy-3-ethoxycarbonyl-3,6-dihydropyrazine aus Piperazin-2,5-dionen 6-Alkyl-2,5-bisethoxy-3-ethoxycarbonyl-3,6-dihydropyrazines from Piperazine-2,5-diones

  摘要：

  DOI：

  10.1002/ardp.19833160716

文献信息

• Lewis acid- and cationic lithium-mediated diastereoselective aldol-type reaction based on a double chiral recognition manner for the asymmetric synthesis of α-substituted serines
  作者：Shigeki Sano、Xiao-Kai Liu、Maki Takebayashi、Yoshimaro Kobayashi、Keiko Tabata、Motoo Shiro、Yoshimitsu Nagao

  DOI：10.1016/0040-4039(95)00725-r

  日期：1995.6

  Diastereoselective aldol-type reaction of ethyl (5R or 5S)-3,6-diethoxy-2,5-dihydro-5-isopropyl-2-pyrazinecarboxylate (5) with chiral aldehyde 7 was investigated by using Sn(OSO2CF3)(2)-N-ethylpiperizine, MgBr2-Et(3)N, n-butyllithium, and lithium diisopropylamide. The mediation mode with Sn(II) between (5R or 5S)-5 and 7 proved to be quite different from that with Mg(II). The two aldol products were converted to the corresponding gamma-lactonic alpha-substituted serines (2S)- and (2R)-10.
• Diastereoselective alkylation of a newly designed bislactim ether towards the asymmetric synthesis of α-alkylated serines
  作者：Shigeki Sano、Maki Takebayashi、Toshio Miwa、Takahiro Ishii、Yoshimitsu Nagao

  DOI：10.1016/s0957-4166(98)00370-x

  日期：1998.10

  Diastereoselective alkylation of ethyl (5S)-3,6-diethoxy-2,5-dihydro-5-isopropyl-2-pyrazinecarboxylate (5S)-3 with alkyl halides was investigated by using NaH and n-BuLi. These alkylated products (2R,5S)-4b-d were converted to the corresponding alpha-alkylated serines (S)-6b-d. (C) 1998 Elsevier Science Ltd. All rights reserved.
• 6-Alkyl-2,5-bisethoxy-3-ethoxycarbonyl-3,6-dihydropyrazine aus Piperazin-2,5-dionen 6-Alkyl-2,5-bisethoxy-3-ethoxycarbonyl-3,6-dihydropyrazines from Piperazine-2,5-diones
  作者：Peter Pachaly、H.-Josef Pelzer

  DOI：10.1002/ardp.19833160716

  日期：——
• Tin- or magnesium-mediated diastereoselective aldol-type reactions for the asymmetric synthesis of α-substituted serines
  作者：Shigeki Sano、Toshio Miwa、Xiao-Kai Liu、Takahiro Ishii、Tomoka Takehisa、Motoo Shiro、Yoshimitsu Nagao

  DOI：10.1016/s0957-4166(98)00371-1

  日期：1998.10

  Diastereoselective aldol-type reactions of ethyl (5S)-3,6-diethoxy-2,5-dihydro-5-isopropyl-2-pyrazine-carboxylate (5S)-3 with achiral aldehydes 8a-d was investigated by using Sn(OSO2CF3)(2)-N-ethylpiperizine and MgBr2-triethylamine. The reaction with Sn(II) between (5S)-3 and aliphatic aldehydes 8a,b proved to be quite different from that with Mg(II). On the other hand, Sn(II)- or Mg(II)-mediated aldol-type reactions of (5S)-3 with benzaldehyde Sc and 3-methyl-2-butenal 8d each afforded the same diastereomer as the major product. These aldol products were each converted to the corresponding alpha-substituted serines 6 and 7 as enantiomerically pure compounds. (C) 1998 Elsevier Science Ltd. AII rights reserved.