3-[(1R)-2-azido-1-hydroxyethyl]phenol | 925430-42-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-[(1R)-2-azido-1-hydroxyethyl]phenol
• CAS: 925430-42-8
• 化学式: C₈H₉N₃O₂
• 分子量: 179.178
• InChiKey: DIDQWHGIEULWJA-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  54.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[(1R)-2-azido-1-hydroxyethyl]phenol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 15.0h， 生成 (R)-norphenylephrine
  参考文献：
  名称：

  Asymmetric Hydrogenation of α-Chloro Aromatic Ketones Catalyzed by η⁶-Arene/TsDPEN−Ruthenium(II) Complexes

  摘要：

  Asymmetric hydrogenation of various alpha-chloro aromatic ketones with Ru(OTf)(TsDPEN)(eta(6)-arene) (TsDPEN = N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine) produces the chiral chlorohydrins in up to 98% ee. This reaction can be conducted even on a 206-g scale. The hydrogenation of an alpha-chloro ketone with a phenol moiety has been utilized for the synthesis of (R)-norphenylephrine without protection-deprotection operations.

  DOI：

  10.1021/ol062661s
• 作为产物：
  描述：

  2-chloro-1-(3-hydroxy phenyl)ethan-1-one 在 Ru(OTf)[(S,S)-TsDPEN](η⁶-mesitylene) sodium azide 、 氢气 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 30.0~100.0 ℃ 、1.01 MPa 条件下， 反应 23.0h， 生成 3-[(1R)-2-azido-1-hydroxyethyl]phenol
  参考文献：
  名称：

  Asymmetric Hydrogenation of α-Chloro Aromatic Ketones Catalyzed by η⁶-Arene/TsDPEN−Ruthenium(II) Complexes

  摘要：

  Asymmetric hydrogenation of various alpha-chloro aromatic ketones with Ru(OTf)(TsDPEN)(eta(6)-arene) (TsDPEN = N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine) produces the chiral chlorohydrins in up to 98% ee. This reaction can be conducted even on a 206-g scale. The hydrogenation of an alpha-chloro ketone with a phenol moiety has been utilized for the synthesis of (R)-norphenylephrine without protection-deprotection operations.

  DOI：

  10.1021/ol062661s

文献信息

• Asymmetric Hydrogenation of α-Chloro Aromatic Ketones Catalyzed by η⁶-Arene/TsDPEN−Ruthenium(II) Complexes
  作者：Takeshi Ohkuma、Kunihiko Tsutsumi、Noriyuki Utsumi、Noriyoshi Arai、Ryoji Noyori、Kunihiko Murata

  DOI：10.1021/ol062661s

  日期：2007.1.1

  Asymmetric hydrogenation of various alpha-chloro aromatic ketones with Ru(OTf)(TsDPEN)(eta(6)-arene) (TsDPEN = N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine) produces the chiral chlorohydrins in up to 98% ee. This reaction can be conducted even on a 206-g scale. The hydrogenation of an alpha-chloro ketone with a phenol moiety has been utilized for the synthesis of (R)-norphenylephrine without protection-deprotection operations.