2-(1-hydroxy-3-methyl-butyl)phenol | 193687-89-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(1-hydroxy-3-methyl-butyl)phenol
• 英文别名: 2-(1-Hydroxy-3-methylbutyl)phenol
• CAS: 193687-89-7
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: JSBLHONOUDJALW-UHFFFAOYSA-N

物化性质

• 沸点：
  280.7±7.0 °C(Predicted)
• 密度：
  1.067±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 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-hydroxy-3-methyl-butyl)phenol 在 manganese(IV) oxide 、 四氯化钛 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 生成 2-Morpholin-4-yl-3-propan-2-ylchromen-4-one
  参考文献：
  名称：

  Targeting the gatekeeper residue in phosphoinositide 3-kinases

  摘要：

  A single residue in the ATP binding pocket of protein kinases-termed the gatekeeper-has been shown to control sensitivity to a wide range of small molecule inhibitors (Chem. Biol. 2004, 11, 691; Chem. Biol. 1999, 6, 671). Kinases that possess a small side chain at this position (Thr, Ala, or Gly) are readily targeted by structurally diverse classes of inhibitors, whereas kinases that possess a larger residue at this position are broadly resistant. Recently, lipid kinases of the phosphoinositide 3-kinase (PI3-K) family have become the focus of intense research interest as potential drug targets (Chem. Biol. 2003, 10, 207; Curr. Opin. Pharmacol. 2003, 3, 426). In this study, we identify the residue that corresponds structurally to the gatekeeper in PI3-Ks, and explore its importance in controlling enzyme activity and small molecule sensitivity. Isoleucine 848 of p110 alpha was mutated to alanine and glycine, but the mutated kinase was found to have severely impaired enzymatic activity. A structural bioinformatic comparison of this kinase with its yeast orthologs identified second site mutations that rescued the enzymatic activity of the 1848A kinase. To probe the dimensions of the gatekeeper pocket, a focused panel of analogs of the PI3-K inhibitor LY294002 was synthesized and its activity against gatekeeper mutated and wild-type p110 alpha was assessed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.021
• 作为产物：
  描述：

  邻甲基苄醇 、 ISOBUTYLMAGNESIUM BROMIDE 以 四氢呋喃 为溶剂， 生成 2-(1-hydroxy-3-methyl-butyl)phenol
  参考文献：
  名称：

  Synthesis of 2,3-Disubstituted Benzofurans fromortho-Acylphenols

  摘要：

  2,3 二甲基苯并呋喃衍生物由邻位苯酚分两步合成。用正-Bu3SnH/AIBN 和 5% HCl-EtOH 处理由邻位苯酚制备的 δ-芳氧基丙烯酸酯，得到 2,3-二取代苯并呋喃。

  DOI：

  10.1055/s-2004-834951

文献信息

• Phosphoric Acid Catalyzed Formation of Hydrogen-Bonded <i>o</i>-Quinone Methides. Enantioselective Cycloaddition with β-Dicarbonyl Compounds toward Benzannulated Oxygen Heterocycles
  作者：Fabian Göricke、Stefan Haseloff、Michael Laue、Maximilian Schneider、Thomas Brumme、Christoph Schneider

  DOI：10.1021/acs.joc.0c01375

  日期：2020.9.18

  A full account of the Brønsted acid catalyzed, enantioselective synthesis of 4H-chromenes and 1H-xanthen-1-ones from o-hydroxybenzyl alcohols and β-dicarbonyl compounds is provided. The central step of our strategy is the BINOL–phosphoric acid catalyzed, enantioselective cycloaddition of β-diketones, β-keto nitriles, and β-keto esters to in situ generated, hydrogen-bonded o-quinone methides. Upon acid-promoted

  提供了由邻羟基苄醇和β-二羰基化合物催化的布朗斯台德酸催化的4 H-色烯和1 H-黄嘌呤-1-酮的对映选择性的完整描述。我们策略的中心步骤是将BINOL-磷酸催化的β-二酮，β-酮腈和β-酮酯的对映选择性环加成反应，使其原位生成氢键合的邻苯二甲酰甲基甲烷。经酸促进的脱水后，通常以优异的收率和对映选择性获得所需产物。进行了详细的机理研究，包括在线NMR和ESI-MS测量，以鉴定相关的合成中间体。由起始醇和反应物可逆形成二聚体观察到邻-苯醌甲基化物处于非循环平衡状态，从而提供了一个储存器，可从该储器中再生邻-苯醌甲基化物并将其再次引入催化循环中。利用反应进程动力学分析确定反应速率的动力学曲线和反应速率常数，该反应速率速率常数揭示了邻醌甲基化物的形成。结合哈米特图，这些研究记录了由取代基提供的电子效应引起的邻醌甲基化物稳定与所述方法的反应速率之间的关系。此外，DFT计算还揭示了一个协调一致但高度异步的[4
• Enantioselective Cyclopropanation/[1,5]-Hydrogen Shift to Access Rauhut–Currier Product
  作者：Seung Tae Kim、Rameshwar Prasad Pandit、Jaesook Yun、Do Hyun Ryu

  DOI：10.1021/acs.orglett.0c03937

  日期：2021.1.1

  A Michael addition initiated cyclopropanation/[1,5]-hydrogen shift has been developed for the enantioselective synthesis of Rauhut–Currier products. The reaction of α-alkyl diazoesters and in situ generated o-quinone methides proceeds in the presence of chiral oxazaborolidinium ion, providing Z-stereocontrolled Rauhut–Currier products in high yields (up to 96%) with excellent Z/E selectivities (>20:1)

  已经开发了迈克尔加成引发的环丙烷化/ [1,5]-氢转移，用于Rauhut-Currier产品的对映选择性合成。α-烷基重氮酸酯与原位生成的邻醌甲基化物的反应在手性恶唑硼烷二鎓离子的存在下进行，可提供高收率（高达96％）的Z-立体控制Rauhut-Currier产品，并具有出色的Z / E选择性（> 20） ：1）和对映选择性（最高> 99％ee）。通过将产物转化为具有两个相邻的手性立体中心的3，4-二氢香豆素来说明合成用途。
• Catalytic Asymmetric Inverse-Electron-Demand Oxa-Diels-Alder Reaction of In Situ Generated<i>ortho</i>-Quinone Methides with 3-Methyl-2-Vinylindoles
  作者：Jia-Jia Zhao、Si-Bing Sun、Sai-Huan He、Qiong Wu、Feng Shi

  DOI：10.1002/anie.201500215

  日期：2015.4.27

  The first catalytic asymmetric inverse‐electron‐demand (IED) oxa‐Diels–Alder reaction of ortho‐quinone methides, generated in situ from ortho‐hydroxybenzyl alcohols, has been established. By selecting 3‐methyl‐2‐vinylindoles as a class of competent dienophiles, this approach provides an efficient strategy to construct an enantioenriched chroman framework with three adjacent stereogenic centers in high

  建立了第一个由邻羟基苯甲醇原位生成的邻醌甲基化物的催化不对称逆电子需求（IED）oxa-Diels-Alder反应。通过选择3-甲基-2-乙烯基吲哚作为一类合格的亲二烯体，该方法提供了一种有效的策略，以高产率和优异的立体选择性（高达99％的产率，> 95：5）构建具有三个相邻的立体异构中心的对映体富集的苯并二氢吡喃骨架。博士，99.5：0.5 er）。利用邻羟基苄醇作为二烯的前体，以及3-甲基-2-乙烯基吲哚作为亲二烯体，以及底物的氢键活化方式，满足了催化不对称IED oxa-Diels-Alder反应的挑战。
• 광학활성화된 라우훗-쿠리어 화합물과 그 제조방법
  申请人：Research ＆ Business Foundation SUNGKYUNKWAN UNIVERSITY 성균관대학교산학협력단(220050013604) BRN ▼101-82-12009

  公开号：KR20220138529A

  公开（公告）日：2022-10-13

  본 발명의 일실시예는 시스(cis) 구조의 광학활성화된 라우훗-쿠리어 화합물과 그 제조방법을 제공한다. 본 발명의 일실시예에 의하면, 시스 구조의 광학활성화된 라우훗-쿠리어 화합물을 제조 가능하며, 시스 구조의 광학활성화된 라우훗-쿠리어 화합물을 통하여 쿠마린의 제조도 가능하다.

  本发明的实施例提供了光学活性的顺式-库仑化合物及其制备方法。根据本发明的实施例，可以制备出光学活性的顺式-库仑化合物，也可以通过光学活性的顺式-库仑化合物制备库马林。
• Chromenes and Chromanones. Part IV.The Birch Reduction of 2,2-Dimethyl-4-chromanone and Its 7-Substituted Analogues
  作者：Czeslaw Wawrzenczyk、Miroslaw Aniol

  DOI：10.3987/com-97-7741

  日期：——