(1R,1'R)-2'-Hydroxy-1'-(phenylethyl)-1-(1-naphthyl)-propylamine | 138234-65-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1R,1'R)-2'-Hydroxy-1'-(phenylethyl)-1-(1-naphthyl)-propylamine
• 英文别名: (2R)-2-[[(1R)-1-naphthalen-1-ylpropyl]amino]-2-phenylethanol
• CAS: 138234-65-8
• 化学式: C₂₁H₂₃NO
• 分子量: 305.42
• InChiKey: MMIJFOALHDEHSH-RTWAWAEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,1'R)-2'-Hydroxy-1'-(phenylethyl)-1-(1-naphthyl)-propylamine 在 lead(IV) acetate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.07h， 以57%的产率得到(R)-α-(1-Naphthyl)propylamine
  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
• 作为产物：
  描述：

  EtCeCl2 、 (4R)-2-(1-萘基)-4-苯基-1,3-恶唑烷 以 四氢呋喃 为溶剂， 以75%的产率得到(1R,1'R)-2'-Hydroxy-1'-(phenylethyl)-1-(1-naphthyl)-propylamine
  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

文献信息

• 1,2- vs. 1,4-addition of nucleophilic organometallics to nonracemic 2-(1-naphthyl)- and 2-cinnamyl-1,3-oxazolidines
  作者：Lendon N. Pridgen、Mohamed K. Mokhallalati、Ming Jung Wu

  DOI：10.1021/jo00030a035

  日期：1992.2

  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.