1-(4-acetylphenyl)ethanol | 15519-23-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-acetylphenyl)ethanol
• 英文别名: 1-[4-(1-Hydroxyethyl)phenyl]ethan-1-one；1-[4-(1-hydroxyethyl)phenyl]ethanone
• CAS: 15519-23-0
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: NWDDTMPWTLSMBS-UHFFFAOYSA-N

物化性质

• 沸点：
  120 °C(Press: 0.5 Torr)
• 密度：
  1.080±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-acetylphenyl)ethanol 生成 乙酮,1-[4-[(1S)-1-羟基乙基]苯基]-(9CI)
  参考文献：
  名称：

  Differentiation and assignment of the proton NMR signals in the bis-MTPA ester of meso-α,α′-dimethyl-1,4-benzenedimethanol

  摘要：

  NaBH4 reduction of one ketone in 1,4-diacetylbenzene followed by Amano PS catalyzed acylation of the R enantiomer, separation of the R acetate from the S alcohol, and reduction of the remaining ketone in each with NaBD4, has provided two mixtures of monodeuterated diol diastereomers: R,R(d) plus R,S(d) and S,R(d) plus S,S(d). Conversion of the unseparated diols into their bis-(R)-MTPA (Mosher's) esters has allowed the NMR signals arising from the C-methyl groups at the R and the S ends of meso-alpha,alpha-dimethyl-1,4-benzenedimethanol bis-(R)-MTPA ester to be assigned unequivocally. Copyright (C) 1996 Published by Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00378-3
• 作为产物：
  描述：

  1-(4-乙基苯)-1-乙醇 在 吡啶 、 甲醇 、 chromium(III) oxide 、 air 、 sodium methylate 、 calcium carbonate 作用下， 生成 1-(4-acetylphenyl)ethanol
  参考文献：
  名称：

  p-Vinylacetophenone: The Disproportionation of p-Acetophenylmethylcarbinol¹

  摘要：

  DOI：

  10.1021/ja01107a520

文献信息

• Silver-Catalyzed Hydrogenation of Ketones under Mild Conditions
  作者：Shengdong Wang、Haiyun Huang、Svetlana Tsareva、Christian Bruneau、Cédric Fischmeister

  DOI：10.1002/adsc.201801523

  日期：2019.2.19

  silver‐catalyzed hydrogenation of ketones using H2 as hydrogen source is reported. Silver nanoparticles are generated from simple silver (I) salts and operate at 25 °C under 20 bar of hydrogen pressure. Various aliphatic and aromatic ketones, including natural products were reduced into the corresponding alcohols in high yields. This silver catalyst allows for the selective hydrogenation of ketones in

  据报道，使用H 2作为氢源，银催化了酮的氢化反应。银纳米粒子由简单的银（I）盐生成，并在25°C和20 bar的氢气压力下运行。各种脂肪族和芳香族酮，包括天然产物，都以高收率被还原成相应的醇。这种银催化剂可以在其他官能团存在的情况下对酮进行选择性加氢。
• Transfer Hydrogenation of Carbonyl Groups, Imines and <i>N</i> ‐Heterocycles Catalyzed by Simple, Bipyridine‐Based Mn ^I Complexes
  作者：Abhishek Dubey、S. M. Wahidur Rahaman、Robert R. Fayzullin、Julia R. Khusnutdinova

  DOI：10.1002/cctc.201900358

  日期：2019.8.21

  Utilization of hydroxy‐substituted bipyridine ligands in transition metal catalysis mimicking [Fe]‐hydrogenase has been shown to be a promising approach in developing new catalysts for hydrogenation. For example, MnI complexes with 6,6′‐dihydroxy‐2,2′‐bipyridine ligand have been previously shown to be active catalysts for CO2 hydrogenation. In this work, simple bipyridine‐based Mn catalysts were developed

  在模拟[Fe]-氢化酶的过渡金属催化中使用羟基取代的联吡啶配体已被证明是开发新型氢化催化剂的一种有前途的方法。例如，先前已证明具有6,6'-二羟基-2,2'-联吡啶配体的Mn I络合物是CO 2加氢的活性催化剂。在这项工作中，开发了简单的基于联吡啶的Mn催化剂，用作酮，醛和亚胺转移加氢的活性催化剂。Mn首次催化N的转移加氢报告了杂环。对于联吡啶中带有两个OH基的配合物，在具有各种取代的配体的配合物中观察到最高的催化活性。氘标记实验提示一价氢途径。
• Acceptorless Dehydrogenation of Alcohols Catalyzed by Cu^I<i>N</i>-Heterocycle Thiolate Complexes
  作者：Da-Wei Tan、Hong-Xi Li、Meng-Juan Zhang、Jian-Lin Yao、Jian-Ping Lang

  DOI：10.1002/cctc.201601459

  日期：2017.3.20

  CuI N‐heterocycle thiolate clusters efficiently catalyze the acceptorless dehydrogenation of alcohols at 70 °C. A variety of secondary/primary benzylic, allylic, and aliphatic alcohols are dehydrogenated to the corresponding ketones and aldehydes in high yields of isolated product upon release of H2. This simple catalytic system is involved in the synthesis of imines through the one‐pot reaction of

  Cu I N杂环硫醇盐簇在70°C时有效催化醇的无受体脱氢。释放H 2时，可以以高收率的分离产物将各种仲/伯苄基，烯丙基和脂族醇脱氢成相应的酮和醛。这个简单的催化系统通过醇和胺的一锅法反应参与亚胺的合成。
• Acceptorless dehydrogenation of amines and alcohols using simple ruthenium chloride
  作者：Muthukumar Kannan、Parul Barteja、Preeti Devi、Senthilkumar Muthaiah

  DOI：10.1016/j.jcat.2020.03.025

  日期：2020.6

  developed for the dehydrogenation of alcohols and amines using simple RuCl3·nH2O and N-benzylhexamethylenetetramine. The in situ catalyst system efficiently oxidized the primary and secondary amines and secondary alcohols into nitrile, imine and ketone products, respectively in moderate to excellent yields. The developed catalyst system was also found to be efficient for the dehydrogenation of N-heterocyles

  一个高效，经济和环境友好的催化剂体系已被开发用于使用简单的RuCl醇和胺的脱氢3 ·nH的2 O和Ñ - benzylhexamethylenetetramine。的原位催化剂体系有效地氧化的伯和仲胺和仲醇成腈，亚胺和酮的产品，分别在中度至良好的产率。还发现开发的催化剂体系对于N-杂环的脱氢是有效的。详细的机理研究显示的第一个例子Ñ -苄基六亚甲基四胺（HMTA-Bz）同时充当碱，还原剂和氢化物源，以生成[Ru（II）（H）2 ]物种作为活性催化剂。机理研究还表明，醇和胺的氧化均涉及脱氢途径，其中氢是唯一的副产物。开发的催化剂系统还提供了从液态有机氢载体（LOHC）释放氢的可能平台。
• The Stereoselective Oxidation of <i>para</i> ‐Substituted Benzenes by a Cytochrome P450 Biocatalyst
  作者：Rebecca R. Chao、Ian C.‐K. Lau、Tom Coleman、Luke R. Churchman、Stella A. Child、Joel H. Z. Lee、John B. Bruning、James J. De Voss、Stephen G. Bell

  DOI：10.1002/chem.202102757

  日期：2021.10.21

  The efficient and sustainable hydroxylation, epoxidation and sulfoxidation of a wide range of benzene derivatives using an engineered variant of a bacterial cytochrome P450 enzyme is reported. These reactions were catalyzed with high activity, regioselectivity and total turnover number (up to 20,000) and in certain instances these reactions were achieved with high enanatioselectivity (up to 98 % ee

  报道了使用细菌细胞色素 P450 酶的工程变体对各种苯衍生物进行有效和可持续的羟基化、环氧化和磺化氧化。这些反应以高活性、区域选择性和总转换数（高达 20,000）催化，在某些情况下，这些反应以高对映选择性（高达 98% ee .）实现。