(2S,8S)-2,8-di-acetylamino-2,8-diallyl-5,5-divinylnonanedioic acid dimethyl ester | 940953-90-2

• 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: (2S,8S)-2,8-di-acetylamino-2,8-diallyl-5,5-divinylnonanedioic acid dimethyl ester
• 英文别名: dimethyl (2S,8S)-2,8-diacetamido-5,5-bis(ethenyl)-2,8-bis(prop-2-enyl)nonanedioate
• CAS: 940953-90-2
• 化学式: C₂₅H₃₈N₂O₆
• 分子量: 462.587
• InChiKey: WZEIWSIRVHADRV-JWQCQUIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  33
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,8S)-2,8-di-acetylamino-2,8-diallyl-5,5-divinylnonanedioic acid dimethyl ester 在 Grubbs catalyst first generation 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 3,10-diacetylaminospiro[6.6]trideca-5,12-diene-3,10-dicarboxylic acid dimethyl ester 、 3,10-diacetylaminospiro[6.6]trideca-5,12-diene-3,10-dicarboxylic 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 4-二甲氨基吡啶 、 正丁基锂 、 戴斯-马丁氧化剂 、 sodium amide 、 三氟乙酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 126.0h， 生成 (2S,8S)-2,8-di-acetylamino-2,8-diallyl-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

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.