(R)-β-propyl-γ-dibenzylamino-propylalcohol hydrochloride

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-β-propyl-γ-dibenzylamino-propylalcohol hydrochloride
• 英文别名: (2R)-2-[(dibenzylamino)methyl]pentan-1-ol;hydrochloride
• 化学式: C₂₀H₂₇NO*ClH
• 分子量: 333.901
• InChiKey: QWBNVYWBJJDAIN-VEIFNGETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.52
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  23.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-β-propyl-γ-dibenzylamino-propylalcohol hydrochloride 在 palladium on activated charcoal 氢气 、 重铬酸 作用下， 以 甲醇 、 丙酮 为溶剂， 20.0 ℃ 、413.68 kPa 条件下， 反应 12.0h， 生成 (R)-2-(((tert-butoxycarbonyl)amino)methyl)pentanoic acid
  参考文献：
  名称：

  Enantioselective Organocatalytic Aminomethylation of Aldehydes:  A Role for Ionic Interactions and Efficient Access to β²-Amino Acids

  摘要：

  Organocatalytic Mannich addition of aldehydes to a formaldehyde-derived iminium species catalyzed by proline-derived chiral pyrrolidines provides beta-amino aldehydes with >/=90% ee. Mechanistic analysis of the proline-catalyzed reactions suggests that non-hydrogen-bonded ionic interactions at the Mannich reaction transition state can influence stereochemical outcome. The beta-amino aldehydes from our process bear a substituent adjacent to the carbonyl and can be efficiently converted to protected beta2-amino acids, which are important building blocks for beta-peptide foldamers that display useful biological activities.

  DOI：

  10.1021/ja061731n
• 作为产物：
  描述：

  (R)-β-propyl-γ-dibenzylamino-propylalcohol 在 盐酸 作用下， 以 1,4-二氧六环 、 乙醚 为溶剂， 以72%的产率得到(R)-β-propyl-γ-dibenzylamino-propylalcohol hydrochloride
  参考文献：
  名称：

  WO2007/112358

  摘要：

  公开号：

文献信息

• WO2007/112358
  申请人：——

  公开号：——

  公开（公告）日：——
• Enantioselective Organocatalytic Aminomethylation of Aldehydes:  A Role for Ionic Interactions and Efficient Access to β²-Amino Acids
  作者：Yonggui Chi、Samuel H. Gellman

  DOI：10.1021/ja061731n

  日期：2006.5.1

  Organocatalytic Mannich addition of aldehydes to a formaldehyde-derived iminium species catalyzed by proline-derived chiral pyrrolidines provides beta-amino aldehydes with >/=90% ee. Mechanistic analysis of the proline-catalyzed reactions suggests that non-hydrogen-bonded ionic interactions at the Mannich reaction transition state can influence stereochemical outcome. The beta-amino aldehydes from our process bear a substituent adjacent to the carbonyl and can be efficiently converted to protected beta2-amino acids, which are important building blocks for beta-peptide foldamers that display useful biological activities.