1-(5-(4-bromophenyl)furan-2-yl)ethanone | 36710-32-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(5-(4-bromophenyl)furan-2-yl)ethanone
• 英文别名: 1-[5-(4-bromo-phenyl)-furan-2-yl]-ethanone；5-(p-Bromphenyl)-2-acetyl-furan；1-[5-(4-Bromophenyl)furan-2-yl]ethan-1-one；1-[5-(4-bromophenyl)furan-2-yl]ethanone
• CAS: 36710-32-4
• 化学式: C₁₂H₉BrO₂
• mdl: MFCD02708561
• 分子量: 265.106
• InChiKey: YUKLQPFNXLGHQA-UHFFFAOYSA-N

物化性质

• 熔点：
  91 °C(Solv: hexane (110-54-3))
• 沸点：
  380.5±32.0 °C(Predicted)
• 密度：
  1.431±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 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：

  1-(5-(4-bromophenyl)furan-2-yl)ethanone 在 sodium tetrahydroborate 、 pyridinium hydrobromide perbromide 、 18-冠醚-6 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 生成 1-(5-(4-bromophenyl)furan-2-yl)ethane-1,2-diol
  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：

  2-乙酰基呋喃 、 (4-bromophenyl)diazonium chloride 在 copper dichloride 作用下， 以 水 为溶剂， 反应 24.0h， 以39%的产率得到1-(5-(4-bromophenyl)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

文献信息

• Stereoselective bioreduction of 1-(5-phenylfuran-2-yl)-ethanones mediated by baker's yeast
  作者：Maria Trif、Noémi Hajnalka Kalló、Mara Ana Naghi、László Csaba Bencze

  DOI：10.3109/10242422.2011.638374

  日期：2012.3

  Abstract Baker's yeast mediated reduction of various phenylfuran-2-yl-ethanones has been studied. The influence of the reaction conditions, the type and position of the substituents, as well the presence of various additives on the enantiomeric composition of the products and the reaction yield are discussed. The absolute configuration of the reaction products was established using a retrosynthetic

  摘要 已经研究了贝克酵母介导的各种苯基呋喃-2-基-乙酮的还原。讨论了反应条件、取代基的类型和位置以及各种添加剂的存在对产物对映体组成和反应产率的影响。使用逆合成程序建立反应产物的绝对构型。
• Sequential use of regio- and stereoselective lipases for the efficient kinetic resolution of racemic 1-(5-phenylfuran-2-yl)ethane-1,2-diols
  作者：László Csaba Bencze、Csaba Paizs、Monica Ioana Toşa、Florin Dan Irimie

  DOI：10.1016/j.tetasy.2011.03.006

  日期：2011.3

  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.
• Substituent effects on the stereochemical outcome of the baker’s yeast-mediated biotransformation of α-hydroxy- and α-acetoxymethyl-5-phenylfuran-2-yl-ethanones
  作者：László Csaba Bencze、Csaba Paizs、Monica Ioana Toşa、Florin Dan Irimie

  DOI：10.1016/j.tetasy.2010.02.004

  日期：2010.3

  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.