(S)-1-(3-甲氧基苯基)乙醇 | 129940-69-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: (S)-1-(3-甲氧基苯基)乙醇
• 英文名称: S-(-)-1-(3-methoxyphenyl)ethanol
• 英文别名: (S)-1-(3-methoxyphenyl)ethan-1-ol；1-(3-methoxyphenyl)ethanol；(S)-1-(m-methoxyphenyl)ethanol；1-(3-methoxyphenyl)ethan-1-ol；(S)-1-(3-methoxyphenyl)ethanol；(1S)-1-(3-methoxyphenyl)ethanol
• CAS: 129940-69-8
• 化学式: C₉H₁₂O₂
• mdl: MFCD09863669
• 分子量: 152.193
• InChiKey: ZUBPFBWAXNCEOG-ZETCQYMHSA-N

物化性质

• 沸点：
  248℃
• 密度：
  1.053
• 闪点：
  104℃

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-1-(3-甲氧基苯基)乙醇 在 sodium perborate 、 正丁基锂 、 四甲基乙二胺 、 碘 、 sodium hydride 作用下， 反应 27.5h， 生成 (S)-bis(acetato-O)[2-(1-methoxyethyl)-6-methoxyphenyl]iodine
  参考文献：
  名称：

  New Chiral Hypervalent Iodine Compounds in Asymmetric Synthesis

  摘要：

  The synthesis of new chiral hypervalent iodine compounds 3 and their use in asymmetric oxidative functionalizations are described. The substituents in the chiral moiety and the stereoelectronic properties of the reagents 3, as well as the reaction conditions, have been optimized. Chiral hypervalent iodine compounds 3 have been investigated in the asymmetric dioxytosylation of styrene and in the alpha-oxytosylation of propiophenone as test reactions. X-ray structural analysis of some reagents shows an interaction between the chiral moiety and the iodine resulting in stereoselectivities up to 53% ee in the products.

  DOI：

  10.1021/jo980475x
• 作为产物：
  描述：

  1-(2-氨基-5-甲氧基苯基)-乙酮 在 盐酸 、 lithium aluminium tetrahydride 、 (-)-diisopinocamphenylborane chloride 、 potassium iodide 、 sodium nitrite 作用下， 以 四氢呋喃 为溶剂， 反应 24.33h， 生成 (S)-1-(3-甲氧基苯基)乙醇
  参考文献：
  名称：

  New Chiral Hypervalent Iodine Compounds in Asymmetric Synthesis

  摘要：

  The synthesis of new chiral hypervalent iodine compounds 3 and their use in asymmetric oxidative functionalizations are described. The substituents in the chiral moiety and the stereoelectronic properties of the reagents 3, as well as the reaction conditions, have been optimized. Chiral hypervalent iodine compounds 3 have been investigated in the asymmetric dioxytosylation of styrene and in the alpha-oxytosylation of propiophenone as test reactions. X-ray structural analysis of some reagents shows an interaction between the chiral moiety and the iodine resulting in stereoselectivities up to 53% ee in the products.

  DOI：

  10.1021/jo980475x

文献信息

• Iron- and Cobalt-Catalyzed Asymmetric Hydrosilylation of Ketones and Enones with Bis(oxazolinylphenyl)amine Ligands
  作者：Tomohiko Inagaki、Le Thanh Phong、Akihiro Furuta、Jun-ichi Ito、Hisao Nishiyama

  DOI：10.1002/chem.200903118

  日期：2010.3.8

  Chiral bis(oxazolinylphenyl)amines proved to be efficient auxiliary ligands for iron and cobalt catalysts with high activity for asymmetric hydrosilylation of ketones and asymmetric conjugate hydrosilylation of enones.

  手性双（恶唑啉基苯基）胺被证明是铁和钴催化剂的有效辅助配体，对酮的不对称氢化硅烷化和烯酮的不对称共轭氢化硅烷化具有高活性。
• Iridium and Rhodium Complexes Containing Enantiopure Primary Amine-Tethered <i>N</i>-Heterocyclic Carbenes: Synthesis, Characterization, Reactivity, and Catalytic Asymmetric Hydrogenation of Ketones
  作者：Kai Y. Wan、Florian Roelfes、Alan J. Lough、F. Ekkehardt Hahn、Robert H. Morris

  DOI：10.1021/acs.organomet.7b00915

  日期：2018.2.12

  a bimetallic iridium compound with (S,S)-11 as the bridging ligand. This compound contains interesting NH···Cl and NH···Ir noncovalent intramolecular interactions. Salt (S,S)-12·HPF6 reacts with silver oxide to yield [Ag2((S,S)-12)2](PF6)2 (20). Reagent 20 serves as an efficient transmetalation reagent to deliver to each rhodium in [RhCl(cod)]2 1 equiv of (S,S)-12 as a bidentate ligand to give [Rh(cod)((S

  咪唑鎓盐[（S，S）-t BuNC 3 H 3 NCHPhCHPhNH 2 ] PF 6，（S，S）-11· HPF 6是对映纯的“ Kaibene”配体t Bu-Kaibene （（S，S）-11在N-杂环卡宾（NHC）环-氮原子上具有叔丁基。通过将手性环状氨基磺酸酯与1-叔丁基咪唑回流，可以高产率和高纯度地制备它。同样（（S，S）-12·在咪唑鎓环氮原子上具有异氰酸酯基的HPF 6以相同的方式制备，并用作Mes-Kaibene，（S，S）-12的来源。这些双齿Kaibene配体具有NHC和被手性接头隔开的伯胺。盐（S，S）-11· HPF 6或（S，S）-12· HPF 6与碱和AgI或CuI反应生成总共四个M（Kaibene） 2I化合物（M = Ag或Cu）。在22°C下，胺官能化的咪唑鎓阳离子经过氧化加成到[IrCl（cod）] 2（cod = 1,5-环辛二烯）中的铱（I），生
• Iron(II) Complexes for the Efficient Catalytic Asymmetric Transfer Hydrogenation of Ketones
  作者：Nils Meyer、Alan J. Lough、Robert H. Morris

  DOI：10.1002/chem.200802458

  日期：2009.5.25

  Ferrous efficiency: New achiral and chiral iron complexes containing P‐N‐N‐P diiminodiphosphine ligands display high activity—and in the case of the catalyst shown, high enantioselectivity—in the catalytic transfer hydrogenation of ketones. This is an important step in the journey to replace precious and toxic platinum metal catalysts with cheap and environmentally friendly iron compounds.

  亚铁效率：含有P-N-N-P二亚氨基二膦配体的新型非手性和手性铁络合物在酮的催化转移加氢中显示出高活性（在所示的催化剂中，具有高对映选择性）。这是用廉价且环保的铁化合物替代珍贵和有毒的铂金属催化剂的重要一步。
• Synthesis of rhodium(I) and iridium(I) complexes of chiral N-heterocyclic carbenes and their application to asymmetric transfer hydrogenation
  作者：Gavin Dyson、Jean-Cédric Frison、Adrian C. Whitwood、Richard E. Douthwaite

  DOI：10.1039/b909290k

  日期：——

  and iridium complexes of chiral NHC–phenolimine and NHC–amine ligands have been prepared and studied for asymmetric transfer hydrogenation. X-ray and NMR spectroscopy show that for NHC–phenolimine complexes abstraction of chloride results in a change in ligand coordination from NHC only to chelating NHC–imine. Complexes of NHC–amines are inactive for transfer hydrogenation, whereas complexes of NHC–phenolimines

  铑 和 铱 手性NHC的配合物酚亚胺 和NHC-胺配体已经制备并研究了不对称转移 氢化。X射线和核磁共振波谱 证明对于NHC –酚亚胺 复杂的抽象 氯化物 导致配体配位从NHC变为螯合NHC –亚胺。NHC-胺的配合物对转移没有活性氢化，而NHC-苯酚亚胺的配合物在室温下对一定范围的含芳基酮具有活性。对映选择性对NHC非常敏感ñ-取代基导致主要对映体的转换。
• Rhodium-Catalyzed Asymmetric Hydrosilylation of Ketones Employing a New Ligand Embodying the Bis(oxazolinyl)pyridine Moiety
  作者：J. Jayashankaran、Atanu Ghoshal、Asit Sarkar、Govindaswamy Manickam、R. Kumaran

  DOI：10.1055/s-0029-1219949

  日期：2010.6

  approach to new ligands embodying bis(oxazolinyl)pyridine has been developed, employing palladium-catalyzed Suzuki coupling and base-mediated cyclization as pivotal steps. A rhodium catalyst derived from the ligand 4-(4-ethylphenyl)-2,6-bis(4-isopropyl-4,5-dihydrooxazol-2-yl)pyridine gave excellent enantioselectivity in the asymmetric hydrosilylation of ketones. In addition the electronic effect of remote

  已经开发了一种包含双（恶唑啉基）吡啶的新配体的通用方法，采用钯催化的 Suzuki 偶联和碱介导的环化作为关键步骤。衍生自配体 4-(4-乙基苯基)-2,6-双(4-异丙基-4,5-二氢恶唑-2-基)吡啶的铑催化剂在酮的不对称氢化硅烷化中具有优异的对映选择性。此外还研究了远程取代基对铑催化剂催化活性的电子效应。