(R)-(-)-2-叠氮基-1-(4-苄氧基苯基)-1-乙醇 | 473552-22-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: (R)-(-)-2-叠氮基-1-(4-苄氧基苯基)-1-乙醇
• 英文名称: (R)-(-)-2-azido-1-(4-benzyloxyphenyl)-1-ethanol
• 英文别名: (R)-(-)-2-azido-1-(p-benzyloxyphenyl)ethanol；(1R)-2-azido-1-[4-(benzyloxy)phenyl]ethan-1-ol；(1R)-2-azido-1-(4-phenylmethoxyphenyl)ethanol
• CAS: 473552-22-6
• 化学式: C₁₅H₁₅N₃O₂
• 分子量: 269.303
• InChiKey: DXSZPBOEAIEKEX-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-(-)-2-叠氮基-1-(4-苄氧基苯基)-1-乙醇 在 palladium on activated charcoal dimethyl sulfide borane 、 氢气 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 8.0h， 生成 地诺帕明
  参考文献：
  名称：

  Chemoenzymatic synthesis of (R)- and (S)-tembamide, aegeline and denopamine by a one-pot lipase resolution protocol

  摘要：

  An efficient synthesis of optically active beta-azido alcohols from their ketoazides by a one-pot reduction and an in situ lipase resolution protocol is described. The synthetic utility of this procedure has been illustrated by its application in the practical synthesis of both enantiomers of the natural hydroxyamides, tembamide, aegeline and the cardiac drug denopamine, with high enantioselectivities. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.013
• 作为产物：
  描述：

  (R)-1-(4-benzyloxyphenyl)-2-(p-tolylsulfonyloxy)ethanol 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以91%的产率得到(R)-(-)-2-叠氮基-1-(4-苄氧基苯基)-1-乙醇
  参考文献：
  名称：

  Asymmetric transfer hydrogenation of 2-tosyloxy-1-(4-hydroxyphenyl)ethanone derivatives: synthesis of (R)-tembamide, (R)-aegeline, (R)-octopamine, and (R)-denopamine

  摘要：

  Catalytic transfer hydrogenation of 2-tosyloxy-1-(4-hydroxyphenyl)ethanone derivatives leads to efficient synthesis of (beta-adrenergic agonists, (R)-tembamide, (R)-aegeline, (R)-octopamine, and (R)-denopamine. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.10.046

文献信息

• Application of optically active 1,2-diol monotosylates for synthesis of β-azido and β-amino alcohols with very high enantiomeric purity. Synthesis of enantiopure (R)-octopamine, (R)-tembamide and (R)-aegeline
  作者：Byung Tae Cho、Sang Kyu Kang、Sung Hye Shin

  DOI：10.1016/s0957-4166(02)00322-1

  日期：2002.6
• Chemoenzymatic synthesis of (R)- and (S)-tembamide, aegeline and denopamine by a one-pot lipase resolution protocol
  作者：Ahmed Kamal、Ahmad Ali Shaik、Mahendra Sandbhor、M. Shaheer Malik

  DOI：10.1016/j.tetasy.2004.11.013

  日期：2004.12

  An efficient synthesis of optically active beta-azido alcohols from their ketoazides by a one-pot reduction and an in situ lipase resolution protocol is described. The synthetic utility of this procedure has been illustrated by its application in the practical synthesis of both enantiomers of the natural hydroxyamides, tembamide, aegeline and the cardiac drug denopamine, with high enantioselectivities. (C) 2004 Elsevier Ltd. All rights reserved.
• Asymmetric transfer hydrogenation of 2-tosyloxy-1-(4-hydroxyphenyl)ethanone derivatives: synthesis of (R)-tembamide, (R)-aegeline, (R)-octopamine, and (R)-denopamine
  作者：Do-Min Lee、Jong-Cheol Lee、Nakcheol Jeong、Kee-In Lee

  DOI：10.1016/j.tetasy.2007.10.046

  日期：2007.11

  Catalytic transfer hydrogenation of 2-tosyloxy-1-(4-hydroxyphenyl)ethanone derivatives leads to efficient synthesis of (beta-adrenergic agonists, (R)-tembamide, (R)-aegeline, (R)-octopamine, and (R)-denopamine. (c) 2007 Elsevier Ltd. All rights reserved.