2-(1-羟基-2-苯基乙基)苯酚 | 40473-60-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 2-(1-羟基-2-苯基乙基)苯酚
• 英文名称: 2-(1-hydroxy-2-phenylethyl)phenol
• CAS: 40473-60-7
• 化学式: C₁₄H₁₄O₂
• 分子量: 214.264
• InChiKey: OQOCSCWMMZVDHS-UHFFFAOYSA-N

物化性质

• 熔点：
  79-81 °C
• 沸点：
  368.4±12.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2907299090

反应信息

• 作为反应物：
  描述：

  2-(1-羟基-2-苯基乙基)苯酚 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以42%的产率得到1-(2-羟基苯基)-2-苯基乙酮
  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：

  溴甲苯 、 水杨醛 在 碘 、 magnesium 作用下， 以 乙醚 为溶剂， 反应 1.75h， 生成 2-(1-羟基-2-苯基乙基)苯酚
  参考文献：
  名称：

  原位形成邻醌甲基苯甲酸酯的有机催化膦酰基化

  摘要：

  已经开发出基于N-杂环磷二酰胺酸（NHPAs）的新型布朗斯台德酸催化剂。NHPA催化剂促进了三烷基亚磷酸酯的磷-迈克尔加成反应，以原位生成的邻-醌甲基化物（o- QMs），以1.5摩尔％的催化剂以中等至优异的收率构建二芳基膦酸酯。非对映选择性合成P -手性膦酸酯的酯与二烷基使用的phenylphosphonites实现。

  DOI：

  10.1021/acs.orglett.7b03019

文献信息

• Substituted (.omega.-aminoalkoxy)stilbene derivatives as a new class of anticonvulsants
  作者：Ryoji Kikumoto、Akihiro Tobe、Harukazu Fukami、Kunihiro Ninomiya、Mitsuo Egawa

  DOI：10.1021/jm00371a015

  日期：1984.5

  (omega- aminoalkoxy )stilbene derivatives has been synthesized and screened for anticonvulsant activity. The effect of structural modification of these molecules on the activities has been systematically examined. Potent anticonvulsant activity was displayed by 2-[4-(4-methyl-1 piperazinyl)butoxy]stilbene (20) and some 2-[4-(3-alkoxy-1-piperidino)butoxy]stilbene derivatives (21, 37, 38, and 40), as determined

  已合成了一系列取代的（ω-氨基烷氧基）二苯乙烯衍生物，并筛选了其抗惊厥活性。已经系统地检查了这些分子的结构修饰对活性的影响。2- [4-（4-甲基-1哌嗪基）丁氧基] sti烯（20）和某些2- [4-（3-烷氧基-1-哌啶基）丁氧基] sti烯衍生物（21，37， 38和40），通过最大电击惊厥（MES）和戊四氮诱发的小鼠惊厥试验确定。在大鼠的进一步药理试验中，化合物21的抗MES活性比二苯乙内酰脲和卡马西平更强，其治疗指数优于两种抗癫痫药。
• Silver catalyzed zinc Barbier reaction of benzylic halides in water
  作者：Lothar W. Bieber、Elisabeth C. Storch、Ivani Malvestiti、Margarete F. da Silva

  DOI：10.1016/s0040-4039(98)02199-6

  日期：1998.12

  Benzylic chlorides react in aqueous dibasic potassium phosphate under silver catalysis with aromatic aldehydes in the presence of zinc dust to give 1,2-diaryl alcohols in moderate to good yields. Dimerization to bibenzyls and reduction of the halide are important side reactions. A wide range of substituted aromatic and heteroaromatic aldehydes and of substituted benzylic chlorides can be used. Aliphatic

  在锌粉存在下，在银催化下，苄基氯化物在磷酸二氢钾水溶液中与芳族醛发生反应，以中等至良好的收率得到1,2-二芳基醇。二聚为联苄基和卤化物的还原是重要的副反应。可以使用多种取代的芳族和杂芳族醛以及取代的苄基氯。脂肪醛和酮是不反应的。讨论了金属表面两个SET的机理。
• A Simple Synthesis of Densely Substituted Benzofurans by Domino Reaction of 2-Hydroxybenzyl Alcohols with 2-Substituted Furans
  作者：Anton S. Makarov、Anna E. Kekhvaeva、Petrakis N. Chalikidi、Vladimir T. Abaev、Igor V. Trushkov、Maxim G. Uchuskin

  DOI：10.1055/s-0039-1690000

  日期：2019.10

  Brönsted acid-catalyzed cascade synthesis of densely substituted benzofurans from easily available salicyl alcohols and biomass-derived furans has been developed. The disclosed sequence includes the intermediate formation of 2-(2-hydroxybenzyl)furans that quickly rearrange into functionalized benzofurans. The established protocol was applied for the total synthesis of sugikurojinol B. The Brönsted

  抽象的 已经开发了布朗斯台德酸催化的级联反应，该反应由易于获得的水杨醇和生物质衍生的呋喃进行稠合取代的苯并呋喃的级联反应。公开的序列包括2-（2-羟基苄基）呋喃的中间体形成，其快速重排为官能化的苯并呋喃。已建立的方案适用于sugikurojinol B的全合成。 已经开发了布朗斯台德酸催化的级联反应，该反应由易于获得的水杨醇和生物质衍生的呋喃进行稠合取代的苯并呋喃的级联反应。公开的序列包括2-（2-羟基苄基）呋喃的中间体形成，其快速重排为官能化的苯并呋喃。已建立的方案适用于sugikurojinol B的全合成。
• Cadmium-Mediated Carbonyl Benzylation in Tap Water
  作者：Cunliu Zhou、Zhiyong Wang

  DOI：10.1055/s-2005-865293

  日期：——

  Zn/CdCl 2 has been developed as a mediator in the benzylation of various aldehydes in tap water affording the corresponding alcohols in moderate to good yields. The addition of a catalytic amount of InCl 3 increases the yield of benzylation product significantly. It can selectively mediate the benzylation of aldehydes in the presence of ketones. A mechanism involving the formation of a cation it-complex

  Zn/CdCl 2 已被开发用作自来水中各种醛的苄基化的介体，以中等至良好的产率提供相应的醇。添加催化量的InCl 3 显着增加了苄化产物的产率。在酮的存在下，它可以选择性地介导醛的苄基化。基于实验事实提出了一种涉及形成阳离子it-络合物的机理。
• Enantioselective Friedel–Crafts Alkylation of Furans with <i>o</i>-Quinone Methide Using a Chiral Oxazaborolidinium Ion Catalyst
  作者：Yoon Sung Cho、Seung Tae Kim、Do Hyun Ryu

  DOI：10.1021/acs.orglett.2c00404

  日期：2022.3.4

  A chiral Lewis acid-catalyzed enantioselective Friedel–Crafts furan alkylation with in situ-generated o-quinone methides has been developed. In the presence of a chiral oxazaborolidinium ion catalyst, the reaction proceeded in high yield (up to 99%) with excellent enantioselectivity (up to >99% ee).

  已经开发了一种手性路易斯酸催化的对映选择性傅克呋喃烷基化与原位生成的邻醌甲基化物。在手性 oxazaborolidinium 离子催化剂存在下，反应以高产率（高达 99%）和优异的对映选择性（高达 >99% ee）进行。