2-bromo-1-(5-(2-chlorophenyl)furan-2-yl)ethanone | 1225301-69-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-bromo-1-(5-(2-chlorophenyl)furan-2-yl)ethanone
• 英文别名: 2-Bromo-1-[5-(2-chlorophenyl)furan-2-yl]ethanone
• CAS: 1225301-69-8
• 化学式: C₁₂H₈BrClO₂
• 分子量: 299.551
• InChiKey: OUZNUPHDWDLOBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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-bromo-1-(5-(2-chlorophenyl)furan-2-yl)ethanone 在 吡啶 、 Burkholderia cepacia lipase 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 18-冠醚-6 、 水 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 反应 16.5h， 生成 1-(5-(2-chlorophenyl)furan-2-yl)-2-hydroxyethyl acetate
  参考文献：
  名称：

  Sequential use of regio- and stereoselective lipases for the efficient kinetic resolution of racemic 1-(5-phenylfuran-2-yl)ethane-1,2-diols

  摘要：

  Possible routes for the enzymatic transformation of various substituted 1-(5-phenylfuran-2-yl)ethane-1,2-diols and their mono- and diacetylated counterparts were studied. Combining the regioselectivity of LPS mediated acylation of the starting racemic diols, the stereoselectivity of LAK shown in the enantiomer selective transformation of the previously formed racemic primary acetates and the LPS mediated mild hydrolysis-alcoholysis of the resolution products, an efficient preparative scale procedure for the synthesis of various highly enantiomerically enriched (R)- and (S)-phenylfuran-2-yl-ethane-1,2-diols has been developed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.03.006
• 作为产物：
  描述：

  1-[5-(2-氯苯基)-2-呋喃基]乙酮 在 溶剂黄146 、 pyridinium hydrobromide perbromide 作用下， 以 二氯甲烷 为溶剂， 反应 2.08h， 以62%的产率得到2-bromo-1-(5-(2-chlorophenyl)furan-2-yl)ethanone
  参考文献：
  名称：

  Substituent effects on the stereochemical outcome of the baker’s yeast-mediated biotransformation of α-hydroxy- and α-acetoxymethyl-5-phenylfuran-2-yl-ethanones

  摘要：

  In this Letter the baker's yeast-mediated biotransformation of variously substituted alpha-hydroxy- and alpha-acetoxymethyl-5-phenylfuran-2-yl-ethanones is described. The stereochemical outcome of the reactions was strongly influenced by the nature of the substituents on the phenyl ring. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.02.004