2-(2-methoxy-phenyl)-1-phenylethanol | 30314-63-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-(2-methoxy-phenyl)-1-phenylethanol
• 英文别名: 2-(2-methoxyphenyl)-1-phenylethanol；2-(o-Methoxyphenyl)-1-phenyl-ethanol；1-Phenyl-2-o-anisylethanol
• CAS: 30314-63-7
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: SGDZOSZXAQKDQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2909499000

反应信息

• 作为产物：
  描述：

  2-甲氧基溴苄 在 lithium chloro-isopropyl-magnesium chloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.5h， 生成 2-(2-methoxy-phenyl)-1-phenylethanol
  参考文献：
  名称：

  通过硫-镁交换功能化的苄基镁试剂。

  摘要：

  DOI：

  10.1002/anie.200501882

文献信息

• Chiral 2-(2-hydroxyaryl)alcohols (HAROLs) with a 1,4-diol scaffold as a new family of ligands and organocatalysts
  作者：Ömer Dilek、Mustafa A. Tezeren、Tahir Tilki、Erkan Ertürk

  DOI：10.1016/j.tet.2017.11.054

  日期：2018.1

  Efficient and modular syntheses of chiral 2-(2-hydroxyaryl)alcohols (HAROLs), novel 1,4-diols carrying one phenolic and one alcohol hydroxyl group, have been developed which led to generation of a small library of structurally diverse HAROLs in enantiomerically pure form. Of the different HAROLs examined, a HAROL based on the indan backbone exhibited the highest activity and enantioselectivity in the

  高效和模块化的手性2-（2-羟基芳基）醇（HAROLs）的合成，带有一个酚和一个醇羟基的新型1,4-二醇已被开发出来，这导致在对映异构体中生成结构多样的HAROLS小文库纯形式。在考察的不同HAROL中，基于茚满骨架的HAROL在Ti（O i Pr）4（y高达97％， 88％ee）并在三田膦的促进下在Morita-Baylis-Hillman反应中作为氢键供体有机催化剂发挥作用。
• 1,2-Diarylethanols by Alternative Regioselective Reductive Ring-Opening of 2,3-Diaryloxiranes
  作者：Nadia Di Blasio、Maria Teresa Lopardo、Paolo Lupattelli

  DOI：10.1002/ejoc.200800992

  日期：2009.2

  Non-symmetrical trans-2,3-diaryloxiranes have been regioselectively opened by catalytic hydrogenation over Pd/C, NaBH4/Pd and [Cp2TiCl]/H2O. Although in the catalytic hydrogenation reactions the epoxides were mainly opened at the β-carbon with respect to the substituted aryl ring in all cases, with the [Cp2TiCl]/H2O system the regioselectivity was affected by the electronic properties of the aryl residues

  非对称反式-2,3-二芳基环氧乙烷通过在 Pd/C、NaBH4/Pd 和 [Cp2TiCl]/H2O 上的催化氢化而被区域选择性地打开。尽管在催化加氢反应中，环氧化物主要在取代芳环的 β-碳处开环，但在 [Cp2TiCl]/ 体系中，区域选择性受芳基残基电子性质的影响，环氧化物在带有最多电子释放或最少吸电子基团的碳上打开。使用 NaBH4/Pd 系统，根据取代基获得不同的区域异构体。从对映体富集的环氧化物开始，在形成的醇中没有观察到光学纯度的损失。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• β‐Arylation of Racemic Secondary Benzylic Alcohols to Access Enantioenriched β‐Arylated Alcohols
  作者：Wang Miao、Jinyu Zhang、Yanyan Yang、Weijun Tang、Dong Xue、Jianliang Xiao、Huaming Sun、Chao Wang

  DOI：10.1002/anie.202306015

  日期：2023.7.24

  catalyst, the first example of β-arylation of secondary alcohols with aryl bromides has been developed via borrowing hydrogen catalysis enabled by an MPV type hydrogen transfer process. In addition, the enantioconvergent version of the reaction has also been realized under the catalysis of Pd and Ru, allowing for the transformation of racemic secondary alcohols into enantioenriched chiral alcohols with good

  使用单一 Pd 催化剂，通过 MPV 型氢转移过程实现的借氢催化，开发了仲醇与芳基溴的 β-芳基化的第一个例子。此外，在Pd和Ru的催化下也实现了该反应的对映异构体，使得外消旋仲醇转化为具有良好对映选择性的对映异构体丰富的手性醇。
• Photoredox-Driven Three-Component Coupling of Aryl Halides, Olefins, and O₂
  作者：Mark C. Maust、Simon B. Blakey

  DOI：10.1021/acscatal.3c05988

  日期：2024.2.16

  hydroxyarylation reaction that utilizes aryl halides, olefins, and O2 as the reaction components. Crucial to this advance was an oxidative, rather than a reductive, approach to aryl radical generation, which enables reaction tolerance to O2. This methodology displays a broad functional group tolerance with a variety of functionalized aryl halides and a broad array of olefins. Development of this methodology enables

  现代有机合成需要以温和有效的方式将丰富的原料化学品结合在一起的方法。为了帮助实现这一目标，我们开发了一种多组分自由基羟基芳基化反应，该反应利用芳基卤、烯烃和O 2作为反应组分。这一进展的关键是芳基自由基生成的氧化而非还原方法，这使得反应能够耐受 O 2 。该方法显示出对各种官能化芳基卤化物和多种烯烃的广泛官能团耐受性。该方法的开发使得能够从简单的市售起始材料快速获得生物相关的羟基芳基产品。
• Regioselective ring-opening of epoxides with ortho-lithioanisoles catalyzed by BF3·OEt2
  作者：Erkan Ertürk、Mustafa A. Tezeren、Taner Atalar、Tahir Tilki

  DOI：10.1016/j.tet.2012.05.116

  日期：2012.8

  It is presented that a number of o-2-hydroxyalkylanisoles could be efficiently synthesized through the regioselective ring-opening reaction of epoxides with o-lithioanisoles in the presence of BF3 center dot OEt2 Lewis-acid catalyst. Sterically demanding o-lithioanisoles had to be generated by exploiting the combination of (BuLi)-Bu-n and a catalytic amount of TMEDA (0.20 equiv) in Et2O as the lithiator whereas 'normal' anisole could be lithiated at ortho-position by treatment with (BuLi)-Bu-n in THE as usual. Surprisingly, the availability of THE and a catalytic amount of TMEDA (0.20 equiv) in the reaction mixture was found to enhance the reaction yields dramatically. A complex aggregate formation by the co-operative ligation of THF and TMEDA to ortho-lithioanisole(s) was proposed to rationalize the high reactivity achieved in the ring-opening reaction of epoxides. (C) 2012 Elsevier Ltd. All rights reserved.