(all-R)-1,2-bis(methyloctahydro-cyclopenta[b]pyrrol-1-yl-2-carboxylate)ethane | 260429-11-6

• 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: (all-R)-1,2-bis(methyloctahydro-cyclopenta[b]pyrrol-1-yl-2-carboxylate)ethane
• 英文别名: methyl (2R,3aR,6aR)-1-[2-[(2R,3aR,6aR)-2-methoxycarbonyl-3,3a,4,5,6,6a-hexahydro-2H-cyclopenta[b]pyrrol-1-yl]ethyl]-3,3a,4,5,6,6a-hexahydro-2H-cyclopenta[b]pyrrole-2-carboxylate
• CAS: 260429-11-6
• 化学式: C₂₀H₃₂N₂O₄
• 分子量: 364.485
• InChiKey: GHPQNBZQAHKWCN-TYENPDHQSA-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：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙基溴化镁 、 (all-R)-1,2-bis(methyloctahydro-cyclopenta[b]pyrrol-1-yl-2-carboxylate)ethane 以 四氢呋喃 为溶剂， 反应 40.0h， 以42%的产率得到(all-R)-1,2-bis[2-(pentan-3-ol-3-yl)octahydro-cyclopenta[b]pyrrol-1-yl]ethane
  参考文献：
  名称：

  Synthesis and application of C2-symmetrical bis-β-amino alcohols based on the octahydro-cyclopenta[b]pyrrole system in the catalytic enantioselective addition of diethylzinc to benzaldehyde

  摘要：

  Asymmetric catalytic ethylation of benzaldehyde utilizing a series of new, tetradental bis-beta-amino alcohols based on the octahydro-cyclopenta[b]pyrrole system - derived from an industrial waste material - is presented. Attention is focused on steric aspects of the catalyst(-precursor) structure. Furthermore, the catalytic efficiency of the ethylene-bridged, C-2-symmetrical bis-beta-amino alcohols is compared to related 'monomeric' structures. Potent chiral ligands, which are highly effective even at concentrations of below 2 mol%, have been developed reaching excellent enantioselectivities up to 100% ee, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00475-9
• 作为产物：
  描述：

  甲醇 、 (2R,3aR,6aR)-1-[2-[(2R,3aR,6aR)-2-carboxy-3,3a,4,5,6,6a-hexahydro-2H-cyclopenta[b]pyrrol-1-yl]ethyl]-3,3a,4,5,6,6a-hexahydro-2H-cyclopenta[b]pyrrole-2-carboxylic acid 在 氯化亚砜 作用下， 反应 50.0h， 以78%的产率得到(all-R)-1,2-bis(methyloctahydro-cyclopenta[b]pyrrol-1-yl-2-carboxylate)ethane
  参考文献：
  名称：

  Synthesis and application of C2-symmetrical bis-β-amino alcohols based on the octahydro-cyclopenta[b]pyrrole system in the catalytic enantioselective addition of diethylzinc to benzaldehyde

  摘要：

  Asymmetric catalytic ethylation of benzaldehyde utilizing a series of new, tetradental bis-beta-amino alcohols based on the octahydro-cyclopenta[b]pyrrole system - derived from an industrial waste material - is presented. Attention is focused on steric aspects of the catalyst(-precursor) structure. Furthermore, the catalytic efficiency of the ethylene-bridged, C-2-symmetrical bis-beta-amino alcohols is compared to related 'monomeric' structures. Potent chiral ligands, which are highly effective even at concentrations of below 2 mol%, have been developed reaching excellent enantioselectivities up to 100% ee, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00475-9