(R)-1-(benzo[b]furan-3-yl)ethanol | 1059698-12-2

• 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: (R)-1-(benzo[b]furan-3-yl)ethanol
• 英文别名: (R)-1-(benzofuran-3-yl)ethanol；(R)-1-(benzofuran-2-yl)ethan-1-ol；(1R)-1-(1-benzofuran-3-yl)ethan-1-ol；(1R)-1-(1-benzofuran-3-yl)ethanol
• CAS: 1059698-12-2
• 化学式: C₁₀H₁₀O₂
• 分子量: 162.188
• InChiKey: NMCNKLINDNOOQJ-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 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：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(1-苯并呋喃-3-基)乙醇 在 sodium hydride 、 pyridinium hydrobromide perbromide 、 (-)-diisopinocamphenylborane chloride 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 40.5h， 生成 (R)-1-(benzo[b]furan-3-yl)ethanol
  参考文献：
  名称：

  Enantioselective Synthesis of 2- and 3-Benzofuryl b-Amino Alcohols

  摘要：

  Enantioselective reduction of 2- and 3-bromoacetylbenzofurans with (-)-B-chlorodiisopinocampheylborane produced the corresponding bromohydrins which were transformed into (S)-(benzofuran-2-yl)oxirane of 70% ee and (S)-(benzofuran-3-yl)oxirane of 71% ee, respectively. The epoxides treated with primary alkylamines gave the corresponding (S)-1-(benzofuran-2- and -3-yl)-2-(alkylamino)ethanols.

  DOI：

  10.3987/com-00-9143

文献信息

• Baker’s yeast-mediated synthesis of (R)- and (S)-heteroaryl-ethane-1,2-diols
  作者：Paula Veronica Podea、Csaba Paizs、Monica Ioana Toşa、Florin Dan Irimie

  DOI：10.1016/j.tetasy.2008.07.030

  日期：2008.8

  Baker’s yeast-mediated enantioselective bioreduction of 1-(heteroaryl)-2-hydroxyethanones and 2-acetoxy-1-(hetero-aryl)ethanones was used for the enantioselective synthesis of both (R)- and (S)-benzofuranyl-, benzo[b]thiophenyl- and benzo[d]thiazolyl-ethane-1,2-diols.

  贝克的酵母介导的1-（杂芳基）-2-羟基乙酮和2-乙酰氧基-1-（杂芳基）乙酮的对映选择性生物还原被用于（R）-和（S）-苯并呋喃基-苯并的对映选择性合成。[ b ]硫代苯基-和苯并[ d ]噻唑基乙烷-1,2-二醇。
• Lipase-catalyzed kinetic resolution of racemic 1-heteroarylethanols—experimental and QM/MM study
  作者：Monica Toşa、Sarolta Pilbák、Paula Moldovan、Csaba Paizs、Gábor Szatzker、György Szakács、Lajos Novák、Florin-Dan Irimie、László Poppe

  DOI：10.1016/j.tetasy.2008.07.004

  日期：2008.8

  The kinetic resolution of racemic 1-(benzothiazol-2-yl)ethanol rac-2a, 1-(benzo[b]thiophen-2-yl)ethanol rac-2b, 1 -(benzo[b]furan-3-yl)ethanol rac-2c and 1-(benzo[b]thiophen-3-yl)ethanol rac-2d was studied by enantiomer selective acylation catalyzed by a selection of commercially available and in house produced lipases. Alcoholysis of the Corresponding racemic acetates rac-3a-d catalyzed by Candida antarctica lipase B (CaLB) was also investigated. Two racemic 1-heteroarylethanols rac-2a,b were prepared by addition of the corresponding lithiated heteroarylic compounds la,b to acetaldehyde, whereas two others, rac-2c,d were synthesized by the addition of MeMgl onto the corresponding heteroaryl-carbaldehydes 1c,d. The high enantiomer selectivities of CaLB in the acylation of racemic 1-heteroarylethanols rac-2a-d allowed the determination of the enantiomeric preference of these enzymatic acetylation reactions by QM/MM [pm3/uff or hf(3-21+g**)/uff] calculations. For acetylation of each of the racemic alcohols rac-2a-d, four possible tetrahedral intermediate states were Compared and analyzed. (C) 2008 Elsevier Ltd. All rights reserved.
• Chemoenzymatic synthesis of (R)- and (S)-1-heteroarylethanols
  作者：Monica Ioana Toşa、Paula Veronica Podea、Csaba Paizs、Florin Dan Irimie

  DOI：10.1016/j.tetasy.2008.08.023

  日期：2008.9

  A chemoenzymatic methodology for the synthesis of highly enantiomerically enriched (S)- and (R)-1-heteroarylethanols by enantioselective bioreduction with baker's yeast of the Corresponding 1-heteroarylethanones followed by three racemization free chemical steps including a Mitsunobu reaction was developed. (C) 2008 Elsevier Ltd. All rights reserved.
• Enantioselective Synthesis of 2- and 3-Benzofuryl b-Amino Alcohols
  作者：Marek Zaidlewicz、Aldona Chechlowska、Andrzej Prewysz-Kwinto、Andrzej Wojtczak

  DOI：10.3987/com-00-9143

  日期：——

  Enantioselective reduction of 2- and 3-bromoacetylbenzofurans with (-)-B-chlorodiisopinocampheylborane produced the corresponding bromohydrins which were transformed into (S)-(benzofuran-2-yl)oxirane of 70% ee and (S)-(benzofuran-3-yl)oxirane of 71% ee, respectively. The epoxides treated with primary alkylamines gave the corresponding (S)-1-(benzofuran-2- and -3-yl)-2-(alkylamino)ethanols.