(S)-(-)-1-(benzofuran-3-yl)ethanol | 343614-13-1

• 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: (S)-(-)-1-(benzofuran-3-yl)ethanol
• 英文别名: (S)-1-(benzofuran-3-yl)ethanol；(1S)-1-(1-benzofuran-3-yl)ethanol
• CAS: 343614-13-1
• 化学式: C₁₀H₁₀O₂
• 分子量: 162.188
• InChiKey: NMCNKLINDNOOQJ-ZETCQYMHSA-N

物化性质

• 沸点：
  182.2±7.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Predicted)

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

• 作为反应物：
  描述：

  N-羟基邻苯二甲酰亚胺 、 (S)-(-)-1-(benzofuran-3-yl)ethanol 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Chemoenzymatic synthesis of (R)- and (S)-1-heteroarylethanols

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2008.08.023
• 作为产物：
  描述：

  3-vinylbenzofuran 在 (+)-1,2-双((2S,5S)-2,5-二苯基膦)乙烷 、 苯硅烷 、 copper diacetate 、 potassium fluoride 、 potassium hydrogencarbonate 、 双氧水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 32.67h， 以74%的产率得到(S)-(-)-1-(benzofuran-3-yl)ethanol
  参考文献：
  名称：

  Asymmetric Copper Hydride-Catalyzed Markovnikov Hydrosilylation of Vinylarenes and Vinyl Heterocycles

  摘要：

  We report a highly enantioselective CuH-catalyzed Markovnikov hydrosilylation of vinylarenes and vinyl heterocycles. This method has a broad scope and enables both the synthesis of isolable silanes and the conversion of crude products to chiral alcohols. Density functional theory calculations support a mechanism proceeding by hydrocupration followed by sigma-bond metathesis with a hydrosilane.

  DOI：

  10.1021/jacs.6b13029

文献信息

• Tailored sol–gel immobilized lipase preparates for the enzymatic kinetic resolution of heteroaromatic alcohols in batch and continuous flow systems
  作者：Mădălina Elena Moisă、Cristina Georgiana Spelmezan、Cristina Paul、Judith Hajnal Bartha-Vári、László Csaba Bencze、Florin Dan Irimie、Csaba Paizs、Fráncisc Péter、Monica Ioana Toşa

  DOI：10.1039/c7ra10157k

  日期：——

  using various binary or ternary precursor mixtures for the EKR of various chiral heteroaromatic secondary alcohols with benzofuran, benzo[b]thiophen, phenothiazine and 2-phenylthiazol moieties. The operational stability in batch process was studied for five selected systems by performing reuse experiments, using the conversion, enantiomeric excesses and enantiomeric ratio as parameters, demonstrating

  通过微调溶胶-凝胶基质的结构，使用各种二元或三元前体混合物对各种手性杂芳族仲醇的EKR进行制备，可以制备出具有良好的热稳定性和操作稳定性的，来自南极假丝酵母B和荧光假单胞菌的固定化固定化脂肪酶。苯并呋喃，苯并[ b]噻吩，吩噻嗪和2-苯基噻唑部分。通过执行重用实验，使用转化率，对映体过量和对映体比率作为参数，对五个选定系统的批处理过程中的操作稳定性进行了研究，证明了溶胶-凝胶脂肪酶制备物性能对生物催化剂和底物结构的依赖性。以生产率为标准，以连续流模式研究了具有最佳性能的生物催化剂的苯并呋喃底物的分离度。在这两种情况下，连续流操作（r flow）下的比反应速率均高于分批模式（r batch）下的反应速率，从而保持了其在进一步工艺开发中的有用性。
• 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.
• 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.