[R]-1-(2,6-difluorophenyl)-1-ethanol | 126534-39-2

• 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-(2,6-difluorophenyl)-1-ethanol
• 英文别名: (1R)-1-(2,6-difluorophenyl)ethan-1-ol；(1R)-1-(2,6-difluorophenyl)ethanol
• CAS: 126534-39-2
• 化学式: C₈H₈F₂O
• mdl: MFCD09863658
• 分子量: 158.148
• InChiKey: SIYWDKQSSDBLOA-RXMQYKEDSA-N

物化性质

• 沸点：
  182.2±25.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 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：
  3

反应信息

• 作为产物：
  描述：

  2,6-二氟-alpha-甲基苄醇 在 C₂₈H₃₆ClMnN₂O₂ 、 potassium acetate 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.08h， 以95%的产率得到
  参考文献：
  名称：

  手性Mn（iii）-salen配合物与N-溴代琥珀酰亚胺作为强氧化剂催化外消旋仲醇的对映选择性氧化†

  摘要：

  我们证明了使用Mn（III）-salen配合物催化的仲醇的高效对映选择性氧化N-溴琥珀酰亚胺（NBS）作为氧化剂。新方案对于多种仲醇（包括邻位取代的苄醇）的氧化动力学拆分非常有效。

  DOI：

  10.1039/c2ob07087a

文献信息

• Highly Enantioselective Transfer Hydrogenation of Prochiral Ketones Using Ru(II)-Chitosan Catalyst in Aqueous Media
  作者：György Szőllősi、Vanessza Judit Kolcsár

  DOI：10.1002/cctc.201801602

  日期：2019.1.23

  Unprecedentedly high enantioselectivities are obtained in the transfer hydrogenation of prochiral ketones catalyzed by a Ru complex formed in situ with chitosan chiral ligand. This biocompatible, biodegradable chiral polymer obtained from the natural chitin afforded good, up to 86 % enantioselectivities, in the aqueous‐phase transfer hydrogenation of acetophenone derivatives using HCOONa as hydrogen donor. Cyclic

  在与壳聚糖手性配体原位形成的Ru络合物催化的前手性酮的转移氢化中，获得了前所未有的高对映选择性。这种从天然几丁质中获得的生物相容性，可生物降解的手性聚合物，在使用HCOONa作为氢供体的苯乙酮衍生物的水相转移氢化中，提供了高达86％的良好对映选择性。环酮的对映选择性更高，超过90％，而在杂环酮的转移氢化中，进一步增加，最高可达97％。手性催化剂前体制备易地通过扫描电子显微镜，FT-中期和-far-IR光谱法检测。原位结构通过1 H NMR光谱和使用各种壳聚糖衍生物研究了形成的催化剂。结果表明，Ru预催化剂是通过氨基将生物聚合物与金属配位而形成的。加入氢供体后，该前体转化为水不溶性钌氢化物络合物。通过以高收率和光学纯度制备二十多种手性醇，验证了所开发方法的实用价值。在单次结晶后，将催化剂用于以克为单位获得光学纯的手性醇。
• Mechanochemical, Water‐Assisted Asymmetric Transfer Hydrogenation of Ketones Using Ruthenium Catalyst
  作者：Vanessza Judit Kolcsár、György Szőllősi

  DOI：10.1002/cctc.202101501

  日期：2022.2.8

  The first highly efficient, aqueous phase mechanochemical asymmetric transfer hydrogenation of prochiral ketones is reported using in situ formed Noyori-Ikariya Ru-complex and sodium formate as hydrogen donor in ball mill.

  使用原位形成的 Noyori-  Ikariya Ru-配合物和甲酸钠作为球磨机中的氢供体，首次报道了前手性酮的高效水相机械化学不对称转移氢化。
• Origin of Enantioselectivity in the Ru(arene)(amino alcohol)-Catalyzed Transfer Hydrogenation of Ketones
  作者：Peter Brandt、Peter Roth、Pher G. Andersson

  DOI：10.1021/jo030378q

  日期：2004.7.1

  The origin of the enantioselectivity in the ruthenium-catalyzed transfer hydrogenation has been studied by means of experiment and density functional theory calculations. The results clearly show that electrostatic effects are of importance, not only in the T-shaped arene-aryl interaction in the favored transition state but also between the aryl of the substrate and the amine ligand in the disfavored TS. In addition, the electrostatic interaction between the alkyl substituent of the substrate and the catalyst is of importance to the enantioselectivity. The major cause of enantioselection is found to be of nonelectrostatic origin. This inherent property of the catalytic system is discussed in terms of dispersion forces and solvent effects. Finally, a minor but well-characterized steric effect was identified. The success of this class of catalysts in the reduction of alkyl aryl ketones is based on the fact that all factors work in the same direction.
• Relationship between the structure and enantioselectivity in the asymmetric reduction of 2′,6′-disubstituted acetophenones with DIP-ChlorideTM. An ab initio study
  作者：P.Veeraraghavan Ramachandran、Baoqing Gong、Herbert C. Brown、Joseph S. Francisco

  DOI：10.1016/j.tetlet.2004.01.146

  日期：2004.3

  Using computational and chemical studies, a relationship between the % ee achieved and the dihedral angles between the plane of the aromatic ring and the plane containing the carbonyl group has been established for asymmetric reductions with B-chlorodiisopinocampheylborane. (C) 2004 Elsevier Ltd. All rights reserved.
• Asymmetric hydroboration and Matteson homologation for the preparation of fluorinated α-phenethanols
  作者：P. Veeraraghavan Ramachandran、Michael P. Jennings

  DOI：10.1016/j.jfluchem.2007.04.014

  日期：2007.7

  The asymmetric catalytic hydroboration-oxidation of ring-fluorinated styrenes (F-PhCH=CH2) was achieved with catecholborane along with a combination of [Rh(COD)(2)]+BF4- and (R)-BINAP providing 81-96% enantioselectivities for the product alcohols for ortho-unhindered styrenes. A deleterious effect of a 2,6-disubstitution on the enantioselectivity of the product alcohol was observed. 2-Trifluoromethylstyrene also provides only 53% ee, probably due to the steric bulk of the CF3 group at the ortho-position of styrene. Asymmetric homologation of fluorophenylmetals (magnesium bromide or lithium) with pinanediol alpha-chloroethylboronate, followed by oxidation readily furnished the desired 1-(2,6-difluorophenyl)- and 1-(perfluorophenyl)ethanols in 94-95% ee. (c) 2007 Elsevier B.V. All rights reserved.