(R)-1-(2,5-dimethylphenyl)ethanol | 1175672-54-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-1-(2,5-dimethylphenyl)ethanol
• 英文别名: (R)-1-(2,5-dimethylphenyl)ethan-1-ol；1-(2,5-dimethylphenyl)ethanol；(1R)-1-(2,5-dimethylphenyl)ethan-1-ol；(1R)-1-(2,5-dimethylphenyl)ethanol
• CAS: 1175672-54-4
• 化学式: C₁₀H₁₄O
• mdl: MFCD09863736
• 分子量: 150.221
• InChiKey: VHLZFCOCNJEXTQ-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,5-二甲基苯乙酮 在 甲酸 、 C₂₉H₃₄ClN₃O₂RuS₂ 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 168.0h， 以87%的产率得到(R)-1-(2,5-dimethylphenyl)ethanol
  参考文献：
  名称：

  含杂环的 Noyori-Ikariya 催化剂用于酮的不对称转移氢化

  摘要：

  描述了一系列 N-(杂环磺酰基)-官能化 Noyori-Ikariya 催化剂的合成。这些配合物是通过 C2-对称 1,2-二苯基乙烯-1,2-二胺 (DPEN) 的短序列制备的，并通过包括 X 射线晶体学在内的一系列方法进行表征。该配合物是一系列苯乙酮衍生物不对称转移氢化 (ATH) 的活性催化剂，在大多数情况下得到高 ee 的产物，对邻位取代的苯乙酮具有显着的良好效果。

  DOI：

  10.1039/d2dt02411j

文献信息

• Cobalt-catalyzed asymmetric hydrogenation of ketones: A remarkable additive effect on enantioselectivity
  作者：Tian Du、Biwen Wang、Chao Wang、Jianliang Xiao、Weijun Tang

  DOI：10.1016/j.cclet.2020.09.011

  日期：2021.3

  achiral electron-rich mono-phosphine ligand, catalyzes efficient asymmetric hydrogenation of a wide range of aryl ketones, affording chiral alcohols with high yields and moderate to excellent enantioselectivities (29 examples, up to 93% ee). Notably, the achiral mono-phosphine ligand shows a remarkable effect on the enantioselectivity of the reaction.

  手性钴夹钳配合物，与非手性富电子的单膦配体结合，可催化多种芳基酮的有效不对称氢化，提供高收率和中等至优异对映选择性的手性醇（29例，最高93％ee）。值得注意的是，非手性单膦配体对反应的对映选择性表现出显着的影响。
• ASYMMETRIC CATALYST AND PROCESS FOR PREPARING OPTICALLY ACTIVE ALCOHOLS USING THE SAME
  申请人：Watanabe Masahito

  公开号：US20100261924A1

  公开（公告）日：2010-10-14

  The present invention provides an organic metal compound, a ligand, an asymmetric catalyst, and a process for preparing optically-active alcohols using the asymmetric catalyst. The organic metal compound of the present invention is expressed by the following general formula (1): wherein in general formula (1), R 1 and R 2 are a mutually identical or mutually different, unsubstituted or substituted alkyl group, aryl group, cycloalkyl group, or R 1 and R 2 are bound to form an alicyclic ring, R 3 is a hydrogen atom or an alkyl group, R 4 is a branched alkyl group or an alkyl group that does or does not form a ring by itself, or an unsubstituted or substituted aryl group, or an unsubstituted or substituted heterocyclic group, Ar is an unsubstituted or substituted cyclopentadienyl group that is bound to M via a π bond, or an unsubstituted or substituted benzene, X is a hydride group or an anionic group, M is ruthenium, rhodium or iridium, L is a solvent molecule or a water molecule, l is 1 or 2, m is an integer from 0 to 2, n is 0 or 1, and when n is 0, X does not exist, and * represents asymmetric carbon, wherein R 4 is not a camphor group, a camphor derivative group, an isopropyl group or a phenyl group whenever R 1 and R 2 are both a phenyl group.

  本发明提供一种有机金属化合物、配体、不对称催化剂以及利用该不对称催化剂制备光学活性醇的方法。本发明的有机金属化合物由以下通用式（1）表示： 在通用式（1）中，R1和R2是相互相同或相互不同的未取代或取代的烷基基团、芳基团、环烷基团，或R1和R2结合形成脂环，R3是氢原子或烷基基团，R4是支链烷基基团或自身形成环或不形成环的烷基基团，或未取代或取代的芳基团，或未取代或取代的杂环基团，Ar是通过π键与M结合的未取代或取代的环戊二烯基团，或未取代或取代的苯，X是氢化物基团或阴离子基团，M是钌、铑或铱，L是溶剂分子或水分子，l为1或2，m为0到2的整数，n为0或1，当n为0时，X不存在，*代表不对称碳，其中当R1和R2均为苯基团时，R4不是藿香基团、藿香衍生基团、异丙基团或苯基团。
• Catalytic Asymmetric Transfer Hydrogenation of Ketones Using [Ru(p-cymene)Cl2]2 with Chiral Amino Alcohol Ligands
  作者：Sudhindra H. Deshpande、Ashutosh A. Kelkar、Rajesh G. Gonnade、Savita K. Shingote、Raghunath V. Chaudhari

  DOI：10.1007/s10562-010-0408-y

  日期：2010.9

  Catalytic asymmetric transfer hydrogenation of aromatic alkyl ketones has been investigated using [Ru(p-cymene)Cl2]2 and new derivatives of β-amino alcohols synthesized from (S)-(−)-lactic acid and mandelic acid as ligands. Chiral secondary alcohols were obtained with good to excellent conversion (60–90%) and moderate to good enantioselectivities (40–86%).Graphical AbstractAsymmetric transfer hydrogenation

  已经使用 [Ru(p-cymene)Cl2]2 和由 (S)-(-)-乳酸和扁桃酸合成的 β-氨基醇的新衍生物作为配体研究了芳族烷基酮的催化不对称转移氢化。获得了具有良好至优异转化率 (60–90%) 和中等至良好对映选择性 (40–86%) 的手性仲醇。图文摘要使用 [Ru(p-cymene)Cl2]2 和 β 研究了酮的不对称转移氢化-氨基醇由(S)-(-)-乳酸和扁桃酸作为配体合成。获得了具有良好至优异转化率（60-90%）和中等至良好对映选择性（40-86%）的手性仲醇。
• Ruthenium(II) complexes bearing (NNN) ligand: catalytic evaluation of different solvent-mediated coordination modes
  作者：Sara Pellegrino、Giorgio Facchetti、Raffella Gandolfi、Marco Fusè、Emanuela Erba、Isabella Rimoldi

  DOI：10.1139/cjc-2017-0487

  日期：2018.1

  A new (NNN) tridentate ligand was prepared, and its ability to coordinate ruthenium(II) was evaluated. The presence of different functional groups on the ligand allows bi- or tri-coordinated complexes to be obtained depending on complexation conditions. The catalytic activity of both bidentate and tridentate complexes was studied in asymmetric transfer hydrogenation of different aryl ketones, showing a comparable behavior of the two complexes in terms of efficiency and stereoselectivity.

  一种新的（NNN）三牙配体已经制备，并评估了其与钌（II）的配位能力。配体上不同官能团的存在允许根据络合条件获得双或三配位的配合物。研究了双牙和三牙配合物在不同芳基酮的不对称转移氢化反应中的催化活性，显示两种配合物在效率和立体选择性方面表现出可比较的行为。
• Ir(III) complexes of diamine ligands for asymmetric ketone hydrogenation
  作者：José E.D. Martins、Martin Wills

  DOI：10.1016/j.tet.2009.05.012

  日期：2009.7

  The use of a combination of IrCl3 with a series of ligands derived from the C2-symmetric diamine di-phenylethanediamine (DPEN) forms a catalyst capable of the asymmetric hydrogenation of ketones in up to 85% ee. (C) 2009 Elsevier Ltd. All rights reserved.