(2'S,5'R)-2-[2-(5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazin-2-yl)ethyl]malonic acid diethyl ester | 940953-81-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2'S,5'R)-2-[2-(5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazin-2-yl)ethyl]malonic acid diethyl ester
• 英文别名: diethyl 2-[2-[(2S,5R)-3,6-dimethoxy-5-propan-2-yl-2,5-dihydropyrazin-2-yl]ethyl]propanedioate
• CAS: 940953-81-1
• 化学式: C₁₈H₃₀N₂O₆
• 分子量: 370.446
• InChiKey: DYMWZWOSJQODMC-UONOGXRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  95.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2'S,5'R)-2-[2-(5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazin-2-yl)ethyl]malonic acid diethyl ester 在 lithium aluminium tetrahydride 、 sodium hydride 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 2,2-bis-[2-((2S,5R)-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazin-2-yl)ethyl]malonaldehyde
  参考文献：
  名称：

  A stereoselective synthesis of a spiro-bridged bis(α-amino acid) derivative based on Ru(II)-catalysed RCM reactions

  摘要：

  Methodology for a stereoselective synthesis of a member of a novel family of spiro-bridged bis(a-amino acid) derivatives is described. The key step in the construction is a spirane annulation reaction effected by a Ru(Il)-catalysed ring-closing metathesis (RCM) reaction of an appropriately substituted tetraene. The latter became available after stereocontrolled allylations of 3,3-bis[2-((2S,5R)-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazin-2-yl)ethyl]-1,4-pentadiene, which was prepared in several reaction steps from (2R)-2,5-dihydro-2isopropyl-3,6-dimethoxypyrazine as a chiral starting material. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.008
• 作为产物：
  描述：

  (2S,5R)-2-(2'-chloroethyl)-2,5-dihydro-3,6-dimethoxy-5-isopropylpyrazine 在 sodium hydride 、 sodium iodide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 36.0h， 生成 (2'S,5'R)-2-[2-(5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazin-2-yl)ethyl]malonic acid diethyl ester
  参考文献：
  名称：

  A stereoselective synthesis of a spiro-bridged bis(α-amino acid) derivative based on Ru(II)-catalysed RCM reactions

  摘要：

  Methodology for a stereoselective synthesis of a member of a novel family of spiro-bridged bis(a-amino acid) derivatives is described. The key step in the construction is a spirane annulation reaction effected by a Ru(Il)-catalysed ring-closing metathesis (RCM) reaction of an appropriately substituted tetraene. The latter became available after stereocontrolled allylations of 3,3-bis[2-((2S,5R)-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazin-2-yl)ethyl]-1,4-pentadiene, which was prepared in several reaction steps from (2R)-2,5-dihydro-2isopropyl-3,6-dimethoxypyrazine as a chiral starting material. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.008

文献信息

• A stereoselective synthesis of a spiro-bridged bis(α-amino acid) derivative based on Ru(II)-catalysed RCM reactions
  作者：Mioara Andrei、Jon Efskind、Kjell Undheim

  DOI：10.1016/j.tet.2007.03.008

  日期：2007.5

  Methodology for a stereoselective synthesis of a member of a novel family of spiro-bridged bis(a-amino acid) derivatives is described. The key step in the construction is a spirane annulation reaction effected by a Ru(Il)-catalysed ring-closing metathesis (RCM) reaction of an appropriately substituted tetraene. The latter became available after stereocontrolled allylations of 3,3-bis[2-((2S,5R)-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazin-2-yl)ethyl]-1,4-pentadiene, which was prepared in several reaction steps from (2R)-2,5-dihydro-2isopropyl-3,6-dimethoxypyrazine as a chiral starting material. (C) 2007 Elsevier Ltd. All rights reserved.