(R)-1-acetoxy-1-(benzo[b]thiophen-2-yl)ethane | 1059697-84-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: (R)-1-acetoxy-1-(benzo[b]thiophen-2-yl)ethane
• 英文别名: (1R)-1-acetoxy-1-(benzo[b]thiophen-2-yl)ethane；[(1R)-1-(1-benzothiophen-2-yl)ethyl] acetate
• CAS: 1059697-84-5
• 化学式: C₁₂H₁₂O₂S
• 分子量: 220.292
• InChiKey: MECPIMYHIFOJIS-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-苯并噻吩-2-乙醇 、 乙酸-4-氯苯酯 在 dicarbonylhydro[2,5-di(trimethylsilyl)-3,4-butylene-1-hydroxy(η5-cyclopentadienyl)]iron 、 lipase from Candida antarctica 作用下， 以 甲苯 为溶剂， 反应 24.08h， 以95%的产率得到(R)-1-acetoxy-1-(benzo[b]thiophen-2-yl)ethane
  参考文献：
  名称：

  合并铁催化和生物催化—羰基铁配合物作为动态动力学拆分中的高效氢自动转移催化剂

  摘要：

  已经开发了双催化铁/脂肪酶系统，并将其应用于苄基和脂族仲醇的动态动力学拆分。对Knölker型铁配合物的详细研究表明，醇的氢自转移在温和的反应条件下进行，并允许以酶解的方式结合使用。将不同的外消旋醇以良好的收率和优异的对映选择性有效地转化为手性乙酸酯。

  DOI：

  10.1002/anie.201606197

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。
• Asymmetric Chemoenzymatic Reductive Acylation of Ketones by a Combined Iron-Catalyzed Hydrogenation-Racemization and Enzymatic Resolution Cascade
  作者：Osama El-Sepelgy、Aleksandra Brzozowska、Magnus Rueping

  DOI：10.1002/cssc.201700169

  日期：2017.4.22

  A general and practical process for the conversion of prochiral ketones into the corresponding chiral acetates has been realized. An iron carbonyl complex is reported to catalyze the hydrogenation–dehydrogenation–hydrogenation of prochiral ketones. By merging the iron‐catalyzed redox reactions with enantioselective enzymatic acylations a wide range of benzylic, aliphatic and (hetero)aromatic ketones

  已经实现了将前手性酮转化为相应的手性乙酸酯的通用且实用的方法。据报道，羰基铁络合物催化前手性酮的加氢-脱氢-氢化。通过将铁催化的氧化还原反应与对映选择性酶促酰化反应合并，可将各种苄基，脂肪族和（杂）芳族酮以及二酮还原性酰化。分离出高产率和对映选择性的相应产物。铁催化剂与分子氢一起用作氢供体，以及容易获得的乙酸乙酯作为酰基供体一起使用，使得这种级联方法在经济价值和环境信誉方面都非常令人感兴趣。
• 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.