(1S,1'R)-2'-Hydroxy-1'-(phenylethyl)-1-(1-naphthyl)-pentylamine | 138234-67-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1S,1'R)-2'-Hydroxy-1'-(phenylethyl)-1-(1-naphthyl)-pentylamine
• CAS: 138234-67-0
• 化学式: C₂₃H₂₇NO
• 分子量: 333.473
• InChiKey: VKGPAPSIWASERF-GOTSBHOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.39
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  32.26
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  D-苯甘氨醇 在 magnesium sulfate 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 2.0h， 生成 (1S,1'R)-2'-Hydroxy-1'-(phenylethyl)-1-(1-naphthyl)-pentylamine
  参考文献：
  名称：

  1,2- vs. 1,4-addition of nucleophilic organometallics to nonracemic 2-(1-naphthyl)- and 2-cinnamyl-1,3-oxazolidines

  摘要：

  We herein report our results where the addition of organomagnesium reagents to 2-(1-naphthyl)- and 2-cinnamyl-1,3-oxazolidines occurred consistently in a 1,4-conjugate manner, while lithium, cerium, and copper organometallic reagents added in a 1,2-fashion. The 1,4-conjugate addition pathway was primarily exploited by using (4R)-2-(1-naphthyl)-4-phenyl-1,3-oxazolidine (4) as a substrate to obtain, after NaBH4 reduction of the intermediate aldehyde, trans-disubstituted 1,2-dihydronaphthalenes with enantiomeric excesses of 93-94%. The amino alcohol products resulting from 1,2-addition were oxidatively cleaved to afford enantiomeric enriched (R)-alpha-(1-naphthyl)alkylamines 6a and 6b in > 99% ee.

  DOI：

  10.1021/jo00030a035