(S)-(+)-2-chloro-1-(7-ethylbenzofuran-2-yl)ethanol | 537693-72-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (S)-(+)-2-chloro-1-(7-ethylbenzofuran-2-yl)ethanol
• 英文别名: (1S)-2-chloro-1-(7-ethyl-1-benzofuran-2-yl)ethanol
• CAS: 537693-72-4
• 化学式: C₁₂H₁₃ClO₂
• 分子量: 224.687
• InChiKey: JDWLZCFMLFLSNE-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  叔丁胺 、 (S)-(+)-2-chloro-1-(7-ethylbenzofuran-2-yl)ethanol 在 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以56%的产率得到(+)-Bufuralol
  参考文献：
  名称：

  Synthesis of optically active methadones, LAAM and bufuralol by lipase-catalysed acylations

  摘要：

  (R)- and (S)-Methadones and levo-alpha-acetylmethadol (LAAM) have been synthesised starting from lipase-catalysed acylation of dimethylaminopropan-2-ol. An approach to the synthesis of (R)-bufuralol is also presented. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00019-3
• 作为产物：
  描述：

  (R)-1-acetoxy-2-chloro-1-(7-ethylbenzofuran-2-yl)ethane 在 sodium hydroxide 、 Lipase PS 作用下， 以 phosphate buffer 为溶剂， 反应 48.0h， 以53%的产率得到(S)-(+)-2-chloro-1-(7-ethylbenzofuran-2-yl)ethanol
  参考文献：
  名称：

  Synthesis of optically active methadones, LAAM and bufuralol by lipase-catalysed acylations

  摘要：

  (R)- and (S)-Methadones and levo-alpha-acetylmethadol (LAAM) have been synthesised starting from lipase-catalysed acylation of dimethylaminopropan-2-ol. An approach to the synthesis of (R)-bufuralol is also presented. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00019-3

文献信息

• Enantioselective reduction of benzofuryl halomethyl ketones: asymmetric synthesis of (R)-bufuralol
  作者：Marek Zaidlewicz、Agnieszka Tafelska-Kaczmarek、Andrzej Prewysz-Kwinto

  DOI：10.1016/j.tetasy.2005.08.012

  日期：2005.10

  Enantioselective reduction of representative 2-(bromoacetyl)- and 2-(chloroacetyl)benzofurans with (-)-B-chloro-diisopinocampheylborane and by transfer hydrogenation with formic acid/triethylamine in the presence of RhCl[R,R-TsD-PEN](C5Me5) is described. Transfer hydrogenation of the chloro ketones produced the corresponding chlorohydrins of >= 95% ee. (R)-Bufuralol of 96% ce was prepared from the corresponding chloro ketone by transfer hydrogenation-substitution. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis of optically active methadones, LAAM and bufuralol by lipase-catalysed acylations
  作者：Jonathan D. Hull、Feodor Scheinmann、Nicholas J. Turner

  DOI：10.1016/s0957-4166(03)00019-3

  日期：2003.3

  (R)- and (S)-Methadones and levo-alpha-acetylmethadol (LAAM) have been synthesised starting from lipase-catalysed acylation of dimethylaminopropan-2-ol. An approach to the synthesis of (R)-bufuralol is also presented. (C) 2003 Elsevier Science Ltd. All rights reserved.