(R)-(-)-2-amino-1-(p-benzyloxyphenyl)ethanol | 473552-26-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-(-)-2-amino-1-(p-benzyloxyphenyl)ethanol
• 英文别名: (1R)-2-Amino-1-[4-(benzyloxy)phenyl]ethan-1-ol；(1R)-2-amino-1-(4-phenylmethoxyphenyl)ethanol
• CAS: 473552-26-0
• 化学式: C₁₅H₁₇NO₂
• 分子量: 243.305
• InChiKey: YZOUUVUNKGUDSK-HNNXBMFYSA-N

物化性质

• 沸点：
  434.5±40.0 °C(Predicted)
• 密度：
  1.164±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(-)-2-amino-1-(p-benzyloxyphenyl)ethanol 在 palladium on activated charcoal dimethyl sulfide borane 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 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 palladium on activated charcoal sodium azide 、 氢气 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 15.0h， 生成 (R)-(-)-2-amino-1-(p-benzyloxyphenyl)ethanol
  参考文献：
  名称：

  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

  摘要：

  DOI：

  10.1016/s0957-4166(02)00322-1

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.