2-isopropyl-5-methoxyphenol | 71745-50-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-isopropyl-5-methoxyphenol
• 英文别名: 5-methoxy-2-propan-2-ylphenol
• CAS: 71745-50-1
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: ODRKDXWJFUCADH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  2-isopropyl-5-methoxyphenol 在 palladium diacetate 、 sodium acetate 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基乙酰胺 为溶剂， 反应 24.0h， 生成 4-isopropyl-1-methoxy-6H-benzo[b]naphtho[1,2-d]pyran-6-one
  参考文献：
  名称：

  Atropisomerization Barriers of Configurationally Unstable Biaryl Compounds, Useful Substrates for Atroposelective Conversions to Axially Chiral Biaryls

  摘要：

  Configurationally unstable biaryl lactones of type (M)-1 reversible arrow (P)-1 and ring-opened 2-acyl-2'-hydroxy biaryl compounds of type (M)-4 reversible arrow (P)-4 are versatile precursors for the atroposelective preparation of axially chiral biaryls. The activation barriers of their atropisomerization process, which constitutes a fundamental precondition for the dynamic kinetic resolution, were determined by dynamic NMR spectroscopy for rapid processes and by HPLC-monitored racemization of enantiomerically enriched material for smaller interconversion rates. For the lactones, the free activation energies Delta G(298)(double dagger) increase with the steric demand of the substituent R ortho to the biaryl axis in the series H < OMe (t(1/2) approximate to ms) < Me (t(1/2) approximate to s) < Et < i-Pr (t(1/2) approximate to min) < t-Bu (t(1/2) approximate to d). The formally ring-opened 2-acyl-2'-hydroxy biaryls, which interconvert via the lactol isomers 5 as the cyclic (and thus configurationally less stable) intermediates, have a significantly slower atropisomerization rate as a result of the high loss in activation entropy Delta S-double dagger as a consequence of the required intermediate ring closure 4 --> 5.

  DOI：

  10.1021/jo9913356
• 作为产物：
  描述：

  丹皮酚 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 苄基三丁基溴化铵 作用下， 以 甲醇 、 二氯甲烷 、 水 、 苯 为溶剂， 20.0 ℃ 、400.01 kPa 条件下， 反应 30.0h， 生成 2-isopropyl-5-methoxyphenol
  参考文献：
  名称：

  Atropisomerization Barriers of Configurationally Unstable Biaryl Compounds, Useful Substrates for Atroposelective Conversions to Axially Chiral Biaryls

  摘要：

  Configurationally unstable biaryl lactones of type (M)-1 reversible arrow (P)-1 and ring-opened 2-acyl-2'-hydroxy biaryl compounds of type (M)-4 reversible arrow (P)-4 are versatile precursors for the atroposelective preparation of axially chiral biaryls. The activation barriers of their atropisomerization process, which constitutes a fundamental precondition for the dynamic kinetic resolution, were determined by dynamic NMR spectroscopy for rapid processes and by HPLC-monitored racemization of enantiomerically enriched material for smaller interconversion rates. For the lactones, the free activation energies Delta G(298)(double dagger) increase with the steric demand of the substituent R ortho to the biaryl axis in the series H < OMe (t(1/2) approximate to ms) < Me (t(1/2) approximate to s) < Et < i-Pr (t(1/2) approximate to min) < t-Bu (t(1/2) approximate to d). The formally ring-opened 2-acyl-2'-hydroxy biaryls, which interconvert via the lactol isomers 5 as the cyclic (and thus configurationally less stable) intermediates, have a significantly slower atropisomerization rate as a result of the high loss in activation entropy Delta S-double dagger as a consequence of the required intermediate ring closure 4 --> 5.

  DOI：

  10.1021/jo9913356

文献信息

• JANUS KINASE INHIBITOR COMPOUNDS AND METHODS
  申请人：GOODACRE SIMON CHARLES

  公开号：US20100317643A1

  公开（公告）日：2010-12-16

  The invention provides compounds of Formula I, stereoisomers or pharmaceutically acceptable salts thereof, wherein A, B, D, R 1 , R 2 , R 4 and R 5 are defined herein, a pharmaceutical composition that includes a compound of Formula I and methods of use thereof

  这项发明提供了公式I的化合物，其立体异构体或药学上可接受的盐，其中A、B、D、R1、R2、R4和R5在此处被定义，包括公式I化合物的药物组合物以及其使用方法
• Dehydrative C–H Alkylation and Alkenylation of Phenols with Alcohols: Expedient Synthesis for Substituted Phenols and Benzofurans
  作者：Dong-Hwan Lee、Ki-Hyeok Kwon、Chae S. Yi

  DOI：10.1021/ja302710v

  日期：2012.5.2

  well-defined cationic Ru-H complex catalyzes the dehydrative C-H alkylation reaction of phenols with alcohols to form ortho-substituted phenol products. Benzofuran derivatives are efficiently synthesized from the dehydrative C-H alkenylation and annulation reaction of phenols with 1,2-diols. The catalytic C-H coupling method employs cheaply available phenols and alcohols, exhibits a broad substrate scope, tolerates

  明确定义的阳离子 Ru-H 络合物催化苯酚与醇的脱水 CH 烷基化反应，形成邻位取代的苯酚产物。苯并呋喃衍生物是由苯酚与 1,2-二醇的脱水 CH 烯基化和环化反应有效合成的。催化 CH 偶联方法使用廉价的酚类和醇类，表现出广泛的底物范围，耐受羰基和胺官能团，并释放水作为唯一的副产物。
• Enantioselective Desymmetrization of Bisphenol Derivatives via Ir-Catalyzed Allylic Dearomatization
  作者：Ye Wang、Wen-Yun Zhang、Jia-Hao Xie、Zong-Lun Yu、Jia-Hao Tan、Chao Zheng、Xue-Long Hou、Shu-Li You

  DOI：10.1021/jacs.0c09638

  日期：2020.11.11

  99% ee). The high efficiency of this reaction is exemplified by the short reaction time (30 min), low catalyst loading (down to 0.2 mol %), and ability to perform the reaction on a gram-scale. The total syntheses of (+)-tatanan B and (+)-tatanan C were also realized using this Ir-catalyzed allylic dearomatization reaction as a key step.

  天然产物中经常发现具有多个立体中心的螺环己二烯酮，但合成目标仍然具有挑战性。在此，我们报告了通过 Ir 催化的烯丙基脱芳构化反应对双酚衍生物进行对映选择性去对称化，以良好的产率（高达 90%）和出色的对映选择性（高达 99% ee）提供具有多达三个连续立体中心的螺环己二烯酮衍生物。该反应的高效率体现在反应时间短（30 分钟）、催化剂负载量低（低至 0.2 mol%）以及以克规模进行反应的能力。(+)-tatanan B 和 (+)-tatanan C 的全合成也是使用这种 Ir 催化的烯丙基脱芳构化反应作为关键步骤来实现的。
• Efficient Deprotection of Phenol Methoxymethyl Ethers Using a Solid Acid Catalyst with Wells-Dawson Structure
  作者：G. Romanelli、J. Autino、G. Baronetti、H. Thomas

  DOI：10.3390/61201006

  日期：——

  Deprotection of various phenols from their respective methoxymethyl ethers using an heteropolyacid catalyst was studied. The catalyst was the Wells-Dawson heteropolyacid, used both in bulk or supported on silica. Yields were high to quantitative after less than one hour reaction time and the catalyst was easily recoverable and reusable.

  研究了使用杂多酸催化剂将各种酚从它们各自的甲氧基甲基醚上脱保护。催化剂是 Wells-Dawson 杂多酸，以本体形式使用或负载在二氧化硅上。在不到一小时的反应时间后，收率就很高，而且催化剂很容易回收和重复使用。
• [EN] RSV POLYMERASE INHIBITORS<br/>[FR] INHIBITEURS POLYMERASE RSV
  申请人：BOEHRINGER INGELHEIM CA LTD

  公开号：WO2005042530A1

  公开（公告）日：2005-05-12

  Compounds or enantiomers of formula (I) or a salt thereof: wherein R1, R2, R3, R4 and R5 are as defined herein, are useful for the manufacture of a medicament for the treatment or prevention of respiratory syncytial virus infection in a mammal.

  化合物或式(I)的对映体或盐：其中R1、R2、R3、R4和R5如本文所定义，可用于制造用于治疗或预防哺乳动物呼吸道合胞病毒感染的药物。