1-(5-nitrobenzofuran-2-yl)ethanol | 36739-84-1

• 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: 1-(5-nitrobenzofuran-2-yl)ethanol
• 英文别名: 1-(5-nitro-benzofuran-2-yl)-ethanol；1-(5-Nitro-2-benzofuryl)ethanol；1-(5-Nitro-1-benzofuran-2-yl)ethanol
• CAS: 36739-84-1
• 化学式: C₁₀H₉NO₄
• 分子量: 207.186
• InChiKey: ROFXAZOEFKABSF-UHFFFAOYSA-N

物化性质

• 熔点：
  75 °C(Solv: dichloromethane (75-09-2))
• 沸点：
  362.8±27.0 °C(Predicted)
• 密度：
  1.388±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  79.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(5-nitrobenzofuran-2-yl)ethanol 在 lipase TUB 3b 、 lypozyme TL IM 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 (R)-1-(5-nitrobenzofuran-2-yl)ethanol
  参考文献：
  名称：

  Kinetic resolution of 1-(benzofuran-2-yl)ethanols by lipase-catalyzed enantiomer selective reactions

  摘要：

  Kinetic resolution of racemic 1-(benzofuran-2-yl)ethanols rac-1a-d was performed by lipase-catalyzed enantiomer selective acylation (Emuch greater than100) yielding (1R)-1-acetoxy-1-(benzofuran-2-yl)ethanes (R)-2a-d and (1S)-1-(benzofuran-2-yl)ethanois (S)-1a-d in highly enantiopure form. The degree of enantiomer selectivity for enzymatic alcoholysis/hydrolysis processes starting from racemic 1-acetoxy-1-(benzofuran-2-yl)ethane rac-2 was also tested under various conditions including supercritical CO2 medium. Racemization-free lipase-catalyzed ethanolysis of the (1R)-1-acetoxy-1-(benzofuran-2-yl)ethanes (R)-2a-d yielded almost quantitatively the enantiopure (1R)-1-(benzofuran-2-yl)ethanols (R)-1a-d. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00358-6
• 作为产物：
  描述：

  2-乙酰基-5-硝基苯并[b]呋喃 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以83%的产率得到1-(5-nitrobenzofuran-2-yl)ethanol
  参考文献：
  名称：

  Optically active 1-(benzofuran-2-yl)ethanols and ethane-1,2-diols by enantiotopic selective bioreductions

  摘要：

  Enantiotopic selective reduction of 1-(benzofuran-2-yl)ethanones 1a-d, 1-(benzofuran-2-yl)-2-hydroxyethanones 4a-c and 2-acetoxy-1-(benzofuran-2-yl)ethanones 3a-c was performed by baker's yeast for preparation of optically active (benzofuran-2-yl)carbinols [(S)-5a-d, (S)-6a-c and (R)-6a-c, enantiomeric excess from 55 to 93% ee]. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00222-2

文献信息

• Pd/C mediated synthesis of 2-substituted benzo[b]furans/nitrobenzo[b]furans in water
  作者：Manojit Pal、Venkataraman Subramanian、Koteswar Rao Yeleswarapu

  DOI：10.1016/j.tetlet.2003.09.080

  日期：2003.11

  ns in water has been accomplished via Pd/C catalyzed reaction of o-iodophenols with terminal alkynes in the presence of PPh3, CuI and prolinol. This method can tolerate a variety of functional groups present in the alkynes as well as base labile nitro group in the o-iodophenols. The protocol does not require the use of a phase transfer catalyst or water-soluble phosphine ligands and is free from the

  2-烷基/芳基取代的苯并[一种高效合成b ]呋喃/硝基苯并[ b / C]水呋喃已经经由钯而完成催化反应ö与PPH的存在末端炔烃-iodophenols 3，碘化亚铜和脯氨醇。该方法可以耐受炔烃中存在的各种官能团以及邻碘苯酚中的碱不稳定的硝基。该方案不需要使用相转移催化剂或水溶性膦配体，并且无需使用任何有机助溶剂。
• Optically active 1-(benzofuran-2-yl)ethanols and ethane-1,2-diols by enantiotopic selective bioreductions
  作者：Csaba Paizs、Monica Toşa、Cornelia Majdik、Paula Moldovan、Lajos Novák、Pál Kolonits、Adriana Marcovici、Florin-Dan Irimie、László Poppe

  DOI：10.1016/s0957-4166(03)00222-2

  日期：2003.6

  Enantiotopic selective reduction of 1-(benzofuran-2-yl)ethanones 1a-d, 1-(benzofuran-2-yl)-2-hydroxyethanones 4a-c and 2-acetoxy-1-(benzofuran-2-yl)ethanones 3a-c was performed by baker's yeast for preparation of optically active (benzofuran-2-yl)carbinols [(S)-5a-d, (S)-6a-c and (R)-6a-c, enantiomeric excess from 55 to 93% ee]. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Kinetic resolution of 1-(benzofuran-2-yl)ethanols by lipase-catalyzed enantiomer selective reactions
  作者：Csaba Paizs、Monica Toşa、Viktória Bódai、György Szakács、Ildikó Kmecz、Béla Simándi、Cornelia Majdik、Lajos Novák、Florin-Dan Irimie、László Poppe

  DOI：10.1016/s0957-4166(03)00358-6

  日期：2003.7

  Kinetic resolution of racemic 1-(benzofuran-2-yl)ethanols rac-1a-d was performed by lipase-catalyzed enantiomer selective acylation (Emuch greater than100) yielding (1R)-1-acetoxy-1-(benzofuran-2-yl)ethanes (R)-2a-d and (1S)-1-(benzofuran-2-yl)ethanois (S)-1a-d in highly enantiopure form. The degree of enantiomer selectivity for enzymatic alcoholysis/hydrolysis processes starting from racemic 1-acetoxy-1-(benzofuran-2-yl)ethane rac-2 was also tested under various conditions including supercritical CO2 medium. Racemization-free lipase-catalyzed ethanolysis of the (1R)-1-acetoxy-1-(benzofuran-2-yl)ethanes (R)-2a-d yielded almost quantitatively the enantiopure (1R)-1-(benzofuran-2-yl)ethanols (R)-1a-d. (C) 2003 Elsevier Science Ltd. All rights reserved.