(1R,2S)-2-o-toluamide-1-phenylpropanol | 696659-64-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2S)-2-o-toluamide-1-phenylpropanol
• 英文别名: N-[(1R,2S)-1-hydroxy-1-phenylpropan-2-yl]-2-methylbenzamide
• CAS: 696659-64-0
• 化学式: C₁₇H₁₉NO₂
• 分子量: 269.343
• InChiKey: DFOBTWBPPULYJH-BBRMVZONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2S)-2-o-toluamide-1-phenylpropanol 在 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， 反应 5.0h， 生成 [2-[[(5S)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]methyl]phenyl]-[(4S,5R)-2,2,4-trimethyl-5-phenyl-1,3-oxazolidin-3-yl]methanone
  参考文献：
  名称：

  Asymmetric synthesis of (R)-(+)- and (S)-(−)-2,3-methylenedioxy-8-oxoberbine (gusanlung D)

  摘要：

  The reaction of 6,7-methylenedioxy-3,4-dihydroisoquinoline with laterally lithiated o-toluamides in which the amine part derived from (1S,2S)-thiomicamine or (1R,2S)-2-amino-1-phenylpropanol, affording (R)-(+)- and (S)-(-)-2,3-methylenedioxy-8-oxoberbine in 77% and 64% yield, respectively, and with enantiomeric excess >99% is described. Physical and spectral data of the synthetic product differ from those reported for the natural alkaloid, gusanhang D. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.02.017
• 作为产物：
  描述：

  去甲麻黄碱 、 邻甲基苯甲酰氯 在 氢氧化钾 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.5h， 以99%的产率得到(1R,2S)-2-o-toluamide-1-phenylpropanol
  参考文献：
  名称：

  Asymmetric synthesis of (R)-(+)- and (S)-(−)-2,3-methylenedioxy-8-oxoberbine (gusanlung D)

  摘要：

  The reaction of 6,7-methylenedioxy-3,4-dihydroisoquinoline with laterally lithiated o-toluamides in which the amine part derived from (1S,2S)-thiomicamine or (1R,2S)-2-amino-1-phenylpropanol, affording (R)-(+)- and (S)-(-)-2,3-methylenedioxy-8-oxoberbine in 77% and 64% yield, respectively, and with enantiomeric excess >99% is described. Physical and spectral data of the synthetic product differ from those reported for the natural alkaloid, gusanhang D. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.02.017

文献信息

• Asymmetric synthesis of (R)-(+)- and (S)-(−)-2,3-methylenedioxy-8-oxoberbine (gusanlung D)
  作者：Maria Chrzanowska、Agnieszka Dreas、Maria D. Rozwadowska

  DOI：10.1016/j.tetasy.2004.02.017

  日期：2004.4

  The reaction of 6,7-methylenedioxy-3,4-dihydroisoquinoline with laterally lithiated o-toluamides in which the amine part derived from (1S,2S)-thiomicamine or (1R,2S)-2-amino-1-phenylpropanol, affording (R)-(+)- and (S)-(-)-2,3-methylenedioxy-8-oxoberbine in 77% and 64% yield, respectively, and with enantiomeric excess >99% is described. Physical and spectral data of the synthetic product differ from those reported for the natural alkaloid, gusanhang D. (C) 2004 Elsevier Ltd. All rights reserved.