3,3-bis-[2-((2S,5R)-2-allyl-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazin-2-yl)ethyl]-1,4-pentadiene | 940953-88-8

• 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: 3,3-bis-[2-((2S,5R)-2-allyl-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazin-2-yl)ethyl]-1,4-pentadiene
• 英文别名: (2R,5S)-5-[3-[2-[(2R,5S)-3,6-dimethoxy-2-propan-2-yl-5-prop-2-enyl-2H-pyrazin-5-yl]ethyl]-3-ethenylpent-4-enyl]-3,6-dimethoxy-2-propan-2-yl-5-prop-2-enyl-2H-pyrazine
• CAS: 940953-88-8
• 化学式: C₃₃H₅₂N₄O₄
• 分子量: 568.8
• InChiKey: WJFIALDXISNZCW-GRAPSOOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  41
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  86.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,3-bis-[2-((2S,5R)-2-allyl-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazin-2-yl)ethyl]-1,4-pentadiene 在 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 120.0h， 以48%的产率得到(2S,8S)-2,8-diallyl-2,8-diamino-5,5-divinylnonanedioic acid dimethyl 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
• 作为产物：
  描述：

  2,2-bis-[2-((2S,5R)-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazin-2-yl)ethyl]propane-1,3-diol 在 正丁基锂 、 戴斯-马丁氧化剂 、 sodium amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 3,3-bis-[2-((2S,5R)-2-allyl-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazin-2-yl)ethyl]-1,4-pentadiene
  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.