2-([1,1'-biphenyl]-4-yl(hydroxy)methyl)phenol | 1644559-97-6

• 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: 2-([1,1'-biphenyl]-4-yl(hydroxy)methyl)phenol
• 英文别名: 2-[Hydroxy-(4-phenylphenyl)methyl]phenol
• CAS: 1644559-97-6
• 化学式: C₁₉H₁₆O₂
• 分子量: 276.335
• InChiKey: PFNHGWOCZOZFDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-([1,1'-biphenyl]-4-yl(hydroxy)methyl)phenol 在 吡啶 、 potassium phosphate 、 四(三苯基膦)钯 、 (R)-6,6'-bis(9-phenanthryl)-1,1'-spirobiindanyl-7,7'-diyl hydrogen phosphate 、 potassium bromide 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 77.0h， 生成 (R)-2-([1,1'-biphenyl]-4-yl(butoxy)methyl)-1,1'-biphenyl
  参考文献：
  名称：

  Organocatalytic Asymmetric Nucleophilic Addition to o-Quinone Methides by Alcohols

  摘要：

  The first catalytic asymmetric intermolecular alcohol conjugate addition to o-quinone methides (o-QMs) is disclosed. Due to reversible C-O bond formation and low nucleophilicity of alcohols, catalytic asymmetric oxa-Michael additions with simple alcohol nucleophiles to establish acyclic oxygenated carbon stereocenters remain scarce. The present reaction represents a rare example of this type. With a suitable chiral acid catalyst, the in situ formation of o-QMs and subsequent conjugate addition proceeded with high efficiency and enantioselectivity. The chiral ether products are versatile precursors to other chiral molecules.

  DOI：

  10.1021/acs.orglett.5b03072
• 作为产物：
  描述：

  2-羟基二苯甲酮 、 2-BIPHENYLMAGNESIUM BROMIDE 以 四氢呋喃 为溶剂， 生成 2-([1,1'-biphenyl]-4-yl(hydroxy)methyl)phenol
  参考文献：
  名称：

  通过意外的[4 + 2]环烷基硫醚与邻羟基苄醇合成2H-Chromenes。

  摘要：

  通过意外的正式的[4 + 2]环合反应，开发了一种新型的布朗斯台德酸催化炔基硫醚与邻羟基苄醇的反应。这种不含金属的方案可在温和的反应条件下轻松，实用地合成有价值的多取代2H-色烯，收率通常良好至极佳，并且具有广泛的底物范围和出色的官能团耐受性。

  DOI：

  10.1021/acs.orglett.9b04421

文献信息

• Lewis Acid Catalyzed [4 + 2] Cycloaddition of <i>N</i>-Tosylhydrazones with <i>ortho</i>-Quinone Methides
  作者：Chun-Ying Wang、Jia-Bin Han、Long Wang、Xiang-Ying Tang

  DOI：10.1021/acs.joc.9b02040

  日期：2019.11.1

  A formal [4 + 2] cycloaddition of N-tosylhydrazones with ortho-quinone methides was developed, affording the facile synthesis of diverse 1,3-oxazine derivatives under mild conditions. In this transformation, N-tosylhydrazones are used as a 1,2-dipole synthon under base-free conditions. Moreover, the substrate scope is broad, and the products are formed with high diastereoselectivities in most of the

  开发了N-甲苯磺酰azo与邻醌甲基化物的正式[4 + 2]环加成反应，可在温和条件下轻松合成各种1,3-恶嗪衍生物。在该转化中，在无碱条件下，将N-甲苯磺酰nes用作1,2-偶极合成子。此外，底物范围广，并且在大多数情况下以高非对映选择性形成产物。
• Brønsted Acid-Catalyzed, Highly Enantioselective Addition of Enamides to In Situ<i>-</i>Generated<i>ortho</i>-Quinone Methides: A Domino Approach to Complex Acetamidotetrahydroxanthenes
  作者：Satyajit Saha、Christoph Schneider

  DOI：10.1002/chem.201406044

  日期：2015.2.2

  The highly enantioselective conjugate addition of enamides and enecarbamates to in situ‐generated ortho‐quinone methides, upon subsequent N,O‐acetalization, gives rise to acetamido‐substituted tetrahydroxanthenes with generally excellent enantio‐ and diastereoselectivities. A chiral BINOL‐based phosphoric acid catalyst controls the enantioselectivity of the carbon–carbon bond‐forming event. The products

  在随后的N，O-乙缩醛化反应中，将烯酰胺和烯氨基甲酸酯高度对映体选择性共轭加成到原位生成的邻苯二甲rise基甲烷中，生成对乙酰氨基取代的四氢氧杂蒽，它们通常具有出色的对映体和非对映体选择性。基于手性BINOL的磷酸催化剂控制碳-碳键形成事件的对映选择性。产物很容易转化为其他基于x吨的杂环。
• Enantioselective Addition of Thiols to ortho-Quinone Methides Catalyzed by Chiral Phosphoric Acids
  作者：Jianwei Sun、Zengwei Lai

  DOI：10.1055/s-0035-1560546

  日期：——

  The first Bronsted acid catalyzed enantioselective addition of thiols to the in situ generated ortho-quinone methides (o-QMs) is described. Complementary to the chiral amine catalyzed approach, the present reaction employs a chiral phosphoric acid as the catalyst. The readily available o-hydroxybenzyl alcohols serve as the atom-economical precursors of o-QMs to react with tritylthiol with moderate

  描述了第一个布朗斯台德酸催化的硫醇对映选择性加成到原位生成的邻醌甲基化物 (o-QMs)。作为手性胺催化方法的补充，本反应使用手性磷酸作为催化剂。容易获得的邻羟基苄醇作为邻 QMs 的原子经济前体，在温和条件下与三苯甲基硫醇以中等至良好的效率和对映选择性反应。
• Cooperative Catalysis for the Highly Diastereo‐ and Enantioselective [4+3]‐Cycloannulation of <i>ortho</i> ‐Quinone Methides and Carbonyl Ylides
  作者：Arun Suneja、Henning Jakob Loui、Christoph Schneider

  DOI：10.1002/anie.201913603

  日期：2020.3.27

  We describe herein a highly diastereo- and enantioselective [4+3]-cycloannulation of ortho-quinone methides and carbonyl ylides to furnish functionalized oxa-bridged dibenzooxacines with excellent yields and stereoselectivity in a single synthetic step. The combination of rhodium and chiral phosphoric acid catalysis working in concert to generate both transient intermediates in situ provides direct

  我们在此描述了邻醌甲基化物和羰基叶立德的高度非对映和对映选择性[4+3]-环化，以在单一合成步骤中提供具有优异产率和立体选择性的官能化氧杂桥联二苯并恶辛。铑和手性磷酸催化的组合协同作用，原位产生两种瞬时中间体，提供了直接获得具有两个四级和一个三级立体中心的复杂双环产物的途径。该产品可以进一步功能化为有价值且对映体高度丰富的构建模块。
• Phosphoric Acid Catalyzed [4 + 1]-Cycloannulation Reaction of <i>ortho</i>-Quinone Methides and Diazoketones: Catalytic, Enantioselective Access toward <i>cis</i>-2,3-Dihydrobenzofurans
  作者：Arun Suneja、Christoph Schneider

  DOI：10.1021/acs.orglett.8b03311

  日期：2018.12.7

  A highly straightforward route to enantiomerically highly enriched cis-2,3-dihydrobenzofurans has been achieved via addition of α-diazocarbonyl compounds to in situ generated o-QMs catalyzed by a chiral Brønsted acid. This catalytic strategy provides a direct access to 2,3-dihydrobenzofurans in high yields and with up to 91:9 dr and 99:1 er at ambient temperature. Moreover, a unique phenonium-type

  通过将α-重氮羰基化合物加到由手性布朗斯台德酸催化的原位生成的o- QMs中，已经获得了一种对映异构体高度浓缩的顺式-2,3-二氢苯并呋喃的非常直接的途径。这种催化策略可直接获得高收率的2,3二氢苯并呋喃，在环境温度下可达91：9 dr和99：1 er。此外，独特的型重排可解释具有反向2,3取代模式的产物形成。