2-chloro-1-(3-methylbenzofuran-2-yl)ethanone | 24673-57-2

• 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: 2-chloro-1-(3-methylbenzofuran-2-yl)ethanone
• 英文别名: 2-Chloro-1-(3-methyl-1-benzofuran-2-yl)ethanone
• CAS: 24673-57-2
• 化学式: C₁₁H₉ClO₂
• 分子量: 208.644
• InChiKey: DIMFAXAFMGPJHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-1-(3-methylbenzofuran-2-yl)ethanone 在 甲酸 、 RhCl[(R,R)-TsDPEN](C5Me5) 、 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 反应 72.0h， 以76%的产率得到(S)-(+)-2-chloro-1-(3-methylbenzofuran-2-yl)ethanol
  参考文献：
  名称：

  Enantioselective reduction of benzofuryl halomethyl ketones: asymmetric synthesis of (R)-bufuralol

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2005.08.012
• 作为产物：
  描述：

  3-甲基苯并呋喃 、 氯乙酰氯 在 三氯化铝 作用下， 以 氯仿 为溶剂， 反应 4.0h， 以48%的产率得到2-chloro-1-(3-methylbenzofuran-2-yl)ethanone
  参考文献：
  名称：

  Enantioselective reduction of benzofuryl halomethyl ketones: asymmetric synthesis of (R)-bufuralol

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2005.08.012

文献信息

• JORDAN S.; MARKWELL R. E., J. CHEM. SOC. PERKIN TRANS., PART 1, 1978, NO 5, 419-422
  作者：JORDAN S.、 MARKWELL R. E.

  DOI：——

  日期：——
• 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.