1-(7-methoxybenzofuran-2-yl)ethanol | 260786-00-3

• 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-(7-methoxybenzofuran-2-yl)ethanol
• 英文别名: 1-(7-Methoxy-1-benzofuran-2-yl)-1-ethanol；1-(7-methoxy-1-benzofuran-2-yl)ethanol
• CAS: 260786-00-3
• 化学式: C₁₁H₁₂O₃
• mdl: MFCD02082714
• 分子量: 192.214
• InChiKey: TWTVUBWIPNITCU-UHFFFAOYSA-N

物化性质

• 沸点：
  313.3±27.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  42.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(7-methoxybenzofuran-2-yl)ethanol 在 Lipozyme TL IM 、 lipase TUB 3b 作用下， 以 乙醇 为溶剂， 反应 168.0h， 生成 (R)-1-(7-methoxybenzofuran-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：

  邻香草醛 在 氢氧化钾 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 1-(7-methoxybenzofuran-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

• Efficient Transfer Hydrogenation of Ketones using Methanol as Liquid Organic Hydrogen Carrier
  作者：Nidhi Garg、Soumen Paira、Basker Sundararaju

  DOI：10.1002/cctc.202000228

  日期：2020.7.6

  an efficient protocol for transfer hydrogenation of ketones using methanol as practical and useful liquid organic hydrogen carrier (LOHC) under Ir(III) catalysis. Various ketones, including electron‐rich/electron‐poor aromatic ketones, heteroaromatic and aliphatic ketones, have been efficiently reduced into their corresponding alcohols. Chemoselective reduction of ketones was established in the presence

  在这里，我们证明了在Ir（III）催化下，使用甲醇作为实用和有用的液态有机氢载体（LOHC）转移酮氢化的有效方案。各种酮，包括富电子/贫电子的芳族酮，杂芳族和脂族酮，已被有效地还原为相应的醇。在温和条件下，在存在各种其他可还原官能团的情况下，确定了酮的化学选择性还原。
• Reductive 3-Silylation of Benzofuran Derivatives via Coupling Reaction with Chlorotrialkylsilane
  作者：Suhua Zheng、Tianyuan Zhang、Hirofumi Maekawa

  DOI：10.1021/acs.joc.0c01995

  日期：2020.11.6

  yields under mild reaction conditions with wide substituent scope. The silyl group introduced on the five-membered ring by the reductive coupling could survive with no elimination throughout the oxidation process. The silylated heteroaromatic skeleton is useful as an intermediate in organic synthesis, and its practical utility was also demonstrated by several transformation reactions.

  镁金属对具有吸电子基团的苯并呋喃进行还原甲硅烷基化反应，随后通过DDQ进行氧化重整化反应，在温和的反应条件下，以较宽的取代范围，以中等至良好的收率选择性形成了较少报道的3-甲硅烷基化苯并呋喃。通过还原偶联在五元环上引入的甲硅烷基可以在整个氧化过程中被消除而存活下来。甲硅烷基化的杂芳族骨架可用作有机合成的中间体，并且其实用性还通过数个转化反应证明。
• 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.