(R)-1-(benzofuran-2-yl)ethanol | 119678-66-9

• 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-(benzofuran-2-yl)ethanol
• 英文别名: 1-(benzofuran-2-yl)ethan-1-ol；(1R)-1-(1-benzofuran-2-yl)ethan-1-ol；(1R)-1-(1-benzofuran-2-yl)ethanol
• CAS: 119678-66-9
• 化学式: C₁₀H₁₀O₂
• mdl: MFCD14705968
• 分子量: 162.188
• InChiKey: SCLFEKBHGKCUPA-SSDOTTSWSA-N

物化性质

• 沸点：
  220 °C(Press: 0.5 Torr)
• 密度：
  1.180±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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：

  乙酸酐 、 (R)-1-(benzofuran-2-yl)ethanol 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 0.08h， 生成 (1R)-1-acetoxy-1-(benzofuran-2-yl)ethane
  参考文献：
  名称：

  Chiral spiroaminoborate ester as a highly enantioselective and efficient catalyst for the borane reduction of furyl, thiophene, chroman, and thiochroman-containing ketones

  摘要：

  Prochiral heteroaryl ketones containing furan, thiophene, chroman, and thiochroman moieties were successfully reduced in the presence of 1-10 mol% of spiroaminoborate ester 1 with different borane sources to afford non-racemic alcohols in up to 99% ee. In addition, modest enantioselectivity, around 80% ee, was achieved in the reduction of linear alpha,beta-unsaturated heteroaryl ketones. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.11.009
• 作为产物：
  描述：

  acetic acid 2-(benzofuran-2-yl)-2-oxo-ethyl ester 在 baker's yeast 、 novozyme 435 作用下， 以 乙醇 、 水 为溶剂， 反应 27.0h， 生成 (R)-1-(benzofuran-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

• Chiral-at-metal iridium complex for efficient enantioselective transfer hydrogenation of ketones
  作者：Cheng Tian、Lei Gong、Eric Meggers

  DOI：10.1039/c6cc00972g

  日期：——

  A bis-cyclometalated iridium(III) complex with metal-centered chirality catalyzes the enantioselective transfer hydrogenation of ketones with high enantioselectivities at low catalyst loadings down to 0.002 mol%. Importantly, the rate of catalysis...

  具有金属中心手性的双环金属化铱（III）络合物在低至0.002 mol％的低催化剂负载下催化具有高对映选择性的酮的对映选择性转移氢化反应。重要的是，催化速率...
• RhIII- and IrIII-Catalyzed Asymmetric Transfer Hydrogenation of Ketones in Water
  作者：Xiaofeng Wu、Xiaohong Li、Antonio Zanotti-Gerosa、Allan Pettman、Jianke Liu、Allan James Mills、Jianliang Xiao

  DOI：10.1002/chem.200701258

  日期：2008.2.27

  formate in neat water is shown to be viable with Rh-TsDPEN and Ir-TsDPEN catalysts, derived in situ from [Cp*MCl2]2 (M=Rh, Ir) and TsDPEN. A variety of ketones were reduced, including nonfunctionalized aryl ketones, heteroaryl ketones, ketoesters, and unsaturated ketones. In comparison with Ir-TsDPEN and the related Ru II catalyst, the Rh III catalyst is most efficient in water, affording enantioselectivities

  研究表明，纯净水中甲酸酯在酮中的不对称转移氢化（ATH）在Rh-TsDPEN和Ir-TsDPEN催化剂上是可行的，该催化剂原位衍生自[Cp * MCl2] 2（M = Rh，Ir）和TsDPEN。还原了多种酮，包括未官能化的芳基酮，杂芳基酮，酮酸酯和不饱和酮。与Ir-TsDPEN和相关的Ru II催化剂相比，Rh III催化剂在水中的效率最高，即使在100-1000的底物/催化剂（S / C）比下，对映选择性高达99％ee。惰性气氛。水相还原显示出高度依赖pH值；对于Rh-和Ir-TsDPEN，TOF大于50 mol mol（-1）h（-1）的最佳pH窗口分别为5.5-10.0和6.5-8.5。在pH窗口之外，根据pH的不同，还原速度会变慢或停滞。但是，对映选择性仅在酸性条件下会腐蚀。在较高的S / C比下，Rh-TsDPEN的ATH水溶液显示出对产物以及副产物的抑制作用。产物抑制似乎至少
• A remarkably effective catalyst for the asymmetric transfer hydrogenation of aromatic ketones in water and air
  作者：Xiaofeng Wu、Daniele Vinci、Takao Ikariya、Jiangliang Xiao

  DOI：10.1039/b507276j

  日期：——

  complex generated in situ from [Cp*RhCl2]2 and (1R,2R)-N-(p-toluenesulfonyl)-1,2-cyclohexanediamine (TsCYDN) serves as a remarkably effective, robust catalyst for the asymmetric transfer hydrogenation of aromatic ketones by HCOONa in water in air, affording alcohols in up to 99% ee.

  由[Cp * RhCl2] 2和（1R，2R）-N-（对甲苯磺酰基）-1,2-环己二胺（TsCYDN）原位生成的Rh（III）络合物对于非对称反应非常有效且稳定在空气中的水中通过HCOONa转移芳族酮的氢化反应，提供的醇含量高达99％ee。
• An Efficient Ir(III) Catalyst for the Asymmetric Transfer Hydrogenation of Ketones in Neat Water
  作者：Jianliang Xiao、Xiaohong Li、John Blacker、Ian Houson、Xiaofeng Wu

  DOI：10.1055/s-2006-932490

  日期：——

  The chiral M-CsDPEN [M = Ru, Rh, Ir; CsDPEN = (R,R,R)- or (S,S,S)-N-camphorsulfonyl-1,2-diphenylethylenediamine] catalysts have been shown to be efficient for the asymmetric transfer hydrogenation (ATH) of aryl ketones by formate in neat water. Of particular note is the Ir-(R,R,R)-CsDPEN catalyst, which catalyzes the ATH of a wide range of ketones and delivers almost full conversions within a few hours at a S/C ratio of 1000 at 40 °C in most cases, with enantioselectivities up to 98% ee.

  手性M-CsDPEN [M = Ru, Rh, Ir; CsDPEN = (R,R,R)- 或 (S,S,S)-N-樟脑磺酰-1,2-二苯基乙二胺]催化剂已被证明是在纯水条件下用甲酸进行芳香酮不对称转移氢化的有效催化剂。特别值得关注的是Ir-(R,R,R)-CsDPEN催化剂，它在大多数情况下，在40°C下以1000的S/C比率催化广泛范围的酮的不对称转移氢化反应，在几个小时内几乎实现完全转化，并且最高可达98%的ee值的手性选择性。
• Biphasic Glycerol/2-MeTHF, Ruthenium-Catalysed Enantioselective Transfer Hydrogenation of Ketones Using Sodium Hypophosphite as Hydrogen Donor
  作者：Carole Guyon、Estelle Métay、Nicolas Duguet、Marc Lemaire

  DOI：10.1002/ejoc.201300506

  日期：2013.8

  Sodium hypophosphite has been used as an efficient hydrogen donor in the transfer hydrogenation of aliphatic and aromatic ketones in the presence of [RuCl2(p-cymene)]2 and 2,2′-bipyridine in water. The corresponding alcohols were isolated in moderate to excellent yields (39–95 %). Good chemoselectivity was observed with ester, nitrile and halide functionalities in the ketones not being reduced. An

  在 [RuCl2(p-cymene)]2 和 2,2'-联吡啶存在于水中的脂肪族和芳香族酮的转移氢化中，次磷酸钠已被用作有效的氢供体。相应的醇以中等至极好的收率 (39–95%) 分离。在未还原酮中的酯、腈和卤化物官能团的情况下观察到良好的化学选择性。已经开发了使用 [RuCl(p-cymene)(R,R)-TsDPEN}] 作为催化剂在甘油/2-MeTHF 双相溶剂混合物中的反应的对映选择性版本，并允许使用出色的化学和对映选择性（高达 97 % ee）。