(2R,1'R)-1-[N-benzyl-N-(2'-methoxy-1'-phenylethyl)amino]pentan-2-ol | 1134564-27-4

• 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: (2R,1'R)-1-[N-benzyl-N-(2'-methoxy-1'-phenylethyl)amino]pentan-2-ol
• 英文别名: (2R)-1-[benzyl-[(1R)-2-methoxy-1-phenylethyl]amino]pentan-2-ol
• CAS: 1134564-27-4
• 化学式: C₂₁H₂₉NO₂
• 分子量: 327.467
• InChiKey: SQCWBBOPUNSGHJ-RTWAWAEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2R,1'R)-N-benzyl-N-(2'-methoxy-1'-phenylethyl)-2-bromopentylamine 在 硫酸 作用下， 以 水 为溶剂， 反应 4.0h， 以57%的产率得到(2R,1'R)-1-[N-benzyl-N-(2'-methoxy-1'-phenylethyl)amino]pentan-2-ol
  参考文献：
  名称：

  Regio- and Stereoselective Ring-Opening Reaction of Chiral Aziridines: A Facile Synthesis of Chiral β-Amino Alcohols

  摘要：

  The reaction of chiral 2-alkylsubstituted aziridines (1a-d) with acetic acid afforded beta-amino alcohols with an (S)-chiral center at the beta position (with respect to oxygen). In contrast, a reaction of the same chiral aziridines with acetyl chloride followed by treatment with water gave beta-amino alcohols that have an (S)-chiral center at the alpha position. In addition, the reaction of the same chiral aziridines with benzyl bromide followed by treatment with 2% sulfuric acid gave the beta-amino alcohols with an (R)-chiral center at the alpha position. Thus, we could control the regioselectivity and stereoselectivity of the ring-opening reaction of chiral aziridines (1a-d).

  DOI：

  10.3987/com-08-11537

文献信息

• Regio- and Stereoselective Ring-Opening Reaction of Chiral Aziridines: A Facile Synthesis of Chiral β-Amino Alcohols
  作者：Kimio Higashiyama、Masataka Matsumura、Hiroshi Kojima、Takayasu Yamauchi

  DOI：10.3987/com-08-11537

  日期：——

  The reaction of chiral 2-alkylsubstituted aziridines (1a-d) with acetic acid afforded beta-amino alcohols with an (S)-chiral center at the beta position (with respect to oxygen). In contrast, a reaction of the same chiral aziridines with acetyl chloride followed by treatment with water gave beta-amino alcohols that have an (S)-chiral center at the alpha position. In addition, the reaction of the same chiral aziridines with benzyl bromide followed by treatment with 2% sulfuric acid gave the beta-amino alcohols with an (R)-chiral center at the alpha position. Thus, we could control the regioselectivity and stereoselectivity of the ring-opening reaction of chiral aziridines (1a-d).