1-(3,4-dichlorophenyl)ethanol | 252963-12-5

• 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: 1-(3,4-dichlorophenyl)ethanol
• 英文别名: (R)-1-(3,4-bischlorophenyl)ethanol；(R)-1-(3,4-dichlorophenyl)ethan-1-ol；(1R)-1-(3,4-dichlorophenyl)ethanol；(R)-1-(3,4-dichlorophenyl)ethanol；1-(3,4-dichlorophenyl)ethan-1-ol；(1R)-1-(3,4-dichlorophenyl)ethan-1-ol
• CAS: 252963-12-5
• 化学式: C₈H₈Cl₂O
• mdl: MFCD09863664
• 分子量: 191.057
• InChiKey: VZTGSONNNMGQNQ-RXMQYKEDSA-N

物化性质

• 沸点：
  271.5±25.0 °C(Predicted)
• 密度：
  1.323±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(3,4-dichlorophenyl)ethanol 、 (+/-) ethyl [6-fluoro-8-(methylsulfonyl)-2,3,4,9-tetrahydro-1H-carbazol-1-yl]acetate 在 偶氮二甲酸二叔丁酯 、 三苯基膦 作用下， 生成
  参考文献：
  名称：

  Potent and highly selective DP1 antagonists with 2,3,4,9-tetrahydro-1H-carbazole as pharmacophore

  摘要：

  We discovered that the introduction of a methyl group to the benzylic position of the N-benzyl group in lead compound 1a has a dramatic effect on improving the binding selectivity of this ligand for the prostanoid receptors DP1 (receptor for prostaglandin D(2)) as compared to TP (receptor for thromboxane A(2)). Based on this discovery, we have synthesized a series of potent and highly selective DP1 antagonists. Among them, compound 1h was identified as a highly selective DP1 antagonist with excellent overall properties. It has a K(i) of 0.43 nM to DP1 in binding assay and an IC(50) of 2.5 nM in the DP1 functional assay. Its selectivity for DP1 over TP (the most potent receptor after DP1) exceeds 750-fold based on both binding and functional assays. These properties make 1h a very potent and highly selective DP1 receptor antagonist suitable for investigating the biological functions of DP1 in normal physiology and models of disease (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.018
• 作为产物：
  描述：

  3,4-二氯苯乙酮 在 {R-4-(3,5-Xyl)2P-12-Ph₂P[2.2]paracyclophane}RuCl₂(S,S)-DPEN potassium tert-butylate 、 氢气 作用下， 以 异丙醇 为溶剂， 25.0 ℃ 、1.0 MPa 条件下， 以98%的产率得到1-(3,4-dichlorophenyl)ethanol
  参考文献：
  名称：

  用于高对映选择性钌催化前手性酮氢化的新型对环烷膦

  摘要：

  描述了一种新的对环烷膦的合成。该配体在钌催化的各种芳族和杂芳族酮的不对称氢化中非常有效。

  DOI：

  10.1055/s-2007-990917

文献信息

• Control of enantioselectivity in the enzymatic reduction of halogenated acetophenone analogs by substituent positions and sizes
  作者：Afifa Ayu Koesoema、Daron M. Standley、Shusuke Ohshima、Mayumi Tamura、Tomoko Matsuda

  DOI：10.1016/j.tetlet.2020.151820

  日期：2020.4

  We utilized acetophenone reductase from Geotrichum candidum NBRC 4597 (GcAPRD), wild type and Trp288Ala mutant, to reduce halogenated acetophenone analogs to their corresponding (S)- and (R)-alcohols beneficial as pharmaceutical intermediates. Reduction by wild type resulted in excellent (S)-enantioselectivity for all of the substrates tested. Meanwhile, reduction by Trp288Ala resulted in high (R)-enantioselectivity

  我们利用了来自白色念珠菌NBRC 4597（Gc APRD），野生型和Trp288Ala突变体的苯乙酮还原酶，将卤代苯乙酮类似物还原为相应的（S）-和（R）-醇，可作为药物中间体。对于所有测试的底物，通过野生型的还原均产生优异的（S）-对映选择性。同时，通过Trp288Ala的还原导致高的（R）-对映选择性，用于还原4'取代的苯乙酮和2'-三氟甲基苯乙酮。除此之外，我们还能够通过卤素取代基的位置和大小来控制Trp288Ala的对映选择性。
• Iridium Catalysts with f-Amphox Ligands: Asymmetric Hydrogenation of Simple Ketones
  作者：Weilong Wu、Shaodong Liu、Meng Duan、Xuefeng Tan、Caiyou Chen、Yun Xie、Yu Lan、Xiu-Qin Dong、Xumu Zhang

  DOI：10.1021/acs.orglett.6b01290

  日期：2016.6.17

  ferrocene aminophosphoxazoline ligands (f-amphox) have been successfully developed and used in iridium-catalytic asymmetric hydrogenation of simple ketones to afford corresponding enantiomerically enriched alcohols under mild conditions with superb activities and excellent enantioselectivities (up to 1 000 000 TON, almost all products up to >99% ee, full conversion). The resulting chiral alcohols and their

  已经成功开发了一系列模块化且富电子的三齿二茂铁氨基磷恶唑啉配体（f-amphox），并用于铱在铱催化的不对称加氢中进行简单的酮加氢，以在温和的条件下提供相应的对映异构体富集的醇，具有出色的活性和出色的对映选择性（最高1 000 000 TON，几乎所有产品的ee都> 99％，完全转换）。所得的手性醇及其衍生物是药物中的重要中间体。
• 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。
• Manganese catalyzed asymmetric transfer hydrogenation of ketones
  作者：Guang-Ya Zhang、Sun-Hong Ruan、Yan-Yun Li、Jing-Xing Gao

  DOI：10.1016/j.cclet.2020.10.023

  日期：2021.4

  The asymmetric transfer hydrogenation (ATH) of a wide range of ketones catalyzed by manganese complex as well as chiral PxNy-type ligand under mild conditions was investigated. Using 2-propanol as hydrogen source, various ketones could be enantioselectively hydrogenated by combining cheap, readily available [MnBr(CO)5] with chiral, 22-membered macrocyclic ligand (R,R,R',R')-CyP2N4 (L5) with 2 mol%

  研究了锰配合物以及手性P x N y型配体在温和条件下催化的多种酮的不对称转移氢化（ATH）。使用2-丙醇作为氢源，可以通过将廉价的，易于获得的[MnBr（CO）5 ]与手性22元大环配体（R，R，R '，R '）-CyP 2 N结合起来，对映异构地氢化各种酮4（L5）具有2 mol％的催化剂负载量，可提供具有高达95％ee的高度有价值的手性醇。
• A Ferrocene-Based NH-Free Phosphine-Oxazoline Ligand for Iridium-Catalyzed Asymmetric Hydrogenation of Ketones
  作者：Yanzhao Wang、Guoqiang Yang、Fang Xie、Wanbin Zhang

  DOI：10.1021/acs.orglett.8b02591

  日期：2018.10.5

  A new type of ferrocene-based phosphine-oxazoline ligand has been prepared over a few simple steps. An iridium complex of this ligand is air stable and exhibits excellent performance for the asymmetric hydrogenation of simple ketones (up to 98% yield, up to 99% ee, and 20 000 S/C). Exo-α,β-unsaturated cyclic ketones could be regiospecifically hydrogenated to give chiral allylic alcohols with good results

  通过几个简单的步骤即可制备出新型的二茂铁基膦-恶唑啉配体。该配体的铱络合物是空气稳定的，并且对于简单的酮的不对称氢化表现出出色的性能（最高98％的收率，最高99％的ee和20000 S / C）。Exo -α，β-不饱和环状酮可被区域特异性氢化，得到手性烯丙基醇，效果良好。这项研究表明，P，N-配体也可以有效地促进Ir催化的不对称氢化反应，而无需NH-氢键辅助。