4-(2-acetylphenyl)phenol | 173738-88-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(2-acetylphenyl)phenol
• 英文别名: 1-[2-(4-Hydroxyphenyl)phenyl]ethanone
• CAS: 173738-88-0
• 化学式: C₁₄H₁₂O₂
• 分子量: 212.248
• InChiKey: KFXOQAVKLXKEKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(2-acetylphenyl)phenol 在 碘苯二乙酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以79%的产率得到3′-hydroxy-3′-methyl-3′H-spiro[cyclohexane-1,1′-isobenzofuran]-2,5-dien-4-one
  参考文献：
  名称：

  通过螺环己二烯酮-氧碳鎓阳离子物种的 PIDA 促进/HFIP 控制的酚酮脱芳环化

  摘要：

  报道了苯碘（III）二乙酸盐促进/1,1,1,3,3,3-六氟异丙醇控制的酚酮脱芳环化，提供了两个结构有趣的支架文库，螺环己二烯酮缩酮及其乙酰氧基化对应物，中等至在温和的条件下获得优异的产量。对照实验揭示了反应通过螺环己二烯酮-氧代碳鎓阳离子物种进行。此外，还实现了原位生成的高价碘 (III) 催化形式，以及通过共轭添加实现产物的后期转化。

  DOI：

  10.1021/acs.joc.2c00482
• 作为产物：
  描述：

  3'-methoxy-3'-methyl-3'H-spirocyclohexa-2,5-diene-1-isobenzofuran-4-one 在 锌铜偶 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以96%的产率得到4-(2-acetylphenyl)phenol
  参考文献：
  名称：

  Intramolecular Anodic Carbon−Carbon Bond Formation from Oxidized Phenol Intermediates. Effect of Oxygenated Substituents on the Yields of Spiro Dienones in Electrochemical and Iodobenzene Diacetate Oxidations

  摘要：

  The single-cell, constant-current anodic oxidation of a series of 4-(2-alkenylaryl)phenols was studied in which the aryl substituents were 2-vinyl-4,5-dimethoxy, 6a; 2-propenyl-4,5-dimethoxy, 9a; 2-vinyl-4,5-methylenedioxy, 6b; 2-propenyl-4,5-methylenedioxy, 9b; 2-vinyl-4-methoxy, 6c; 2-propenyl-4-methoxy, 9c; 2-vinyl-5-methoxy, 6d; and 2-propenyl-5-methoxy, 9d. Two compounds having methoxyl groups on the phenolic ring were also studied: 4-(2'-propenylphenyl)-2-methoxyphenol, 9e, and 4-(2'-propenylphenyl)-3-methoxyphenol, 9f. A novel synthetic route to the methoxy compounds 6c, 9c, 6d, and 9d was developed. This involved as a key step the MAD, bis(2,6-ditert-butyl-4-methylphenoxide)methylaluminum, mediated addition of organolithium and Grignard reagents to functionalize quinol ether derivatives. Anodic oxidation of compounds 6a, 9a, 9b, 6c, 9c, and 9d gave good yields of spiro dienones arising from trapping of the phenoxonium ion by the alkenyl side chain followed by reaction of the resulting cation with methanol. The products from the electrochemical oxidation of these 4-(2'-alkenylaryl)phenols were compared with those obtained from the iodobenzene diacetate oxidations. In general, the compounds that gave good yields of spiro dienones from electrochemical oxidation gave good yields from iodobenzene diacetate oxidations. However, there were two cases in which the results of the two oxidations did not parallel each other. Whereas anodic oxidation of 9f gave a low yield of spiro dienone, the iodobenzene diacetate route gave a 74% yield of this product. In the case of 9d, the opposite effect was noted: the electrochemical route gave a higher yield than did the iodobenzene diacetate oxidation.

  DOI：

  10.1021/jo951799d

文献信息

• [EN] SUBSTITUTED PARA-BIPHENYLOXYMETHYL DIHYDRO OXAZOLOPYRIMIDINONES, PREPARATION AND USE THEREOF<br/>[FR] PARA-BIPHÉNYLOXYMÉTHYL-DIHYDRO-OXAZOLOPYRIMIDINONES SUBSTITUÉES, LEUR PRÉPARATION ET LEUR UTILISATION
  申请人：SANOFI AVENTIS

  公开号：WO2011034828A1

  公开（公告）日：2011-03-24

  The present invention relates to a series of substituted para-biphenyloxymethyl dihydro oxazolopyrimidinones of formula (I) as defined herein. This invention also relates to methods of making these compounds including novel intermediates. The compounds of this invention are modulators of metabotropic glutamate receptors (mGluR), particularly, mGluR2 receptor. Therefore, the compounds of this invention are useful as pharmaceutical agents, especially in the treatment and/or prevention of a variety of central nervous system disorders (CNS), including but not limited to acute and chronic neurodegenerative conditions, psychoses, cognition deficit disorders, convulsions, anxiety, depression, migraine, pain, sleep disorders and emesis.

  本发明涉及一系列以本文所定义的式(I)的取代对联苯氧甲基二氢噁唑吡咯嘧啶酮。本发明还涉及制备这些化合物的方法，包括新颖的中间体。本发明的化合物是代谢型谷氨酸受体（mGluR），特别是mGluR2受体的调节剂。因此，本发明的化合物在药物代理方面是有用的，特别是在治疗和/或预防各种中枢神经系统疾病（CNS），包括但不限于急性和慢性神经退行性疾病、精神病、认知缺陷症、癫痫、焦虑、抑郁、偏头痛、疼痛、睡眠障碍和呕吐等方面。
• Palladium-catalyzed para-selective arylation of phenols with aryl iodides in water
  作者：Zhiqing Wu、Feihua Luo、Si Chen、Zhengkai Li、Haifeng Xiang、Xiangge Zhou

  DOI：10.1039/c3cc44345k

  日期：——

  Highly para-selective palladium-catalyzed direct arylation of phenols with aryl iodides was demonstrated by taking advantage of the formal inverse direct arylation strategy. A series of 4-aryl phenols were synthesised by employing water as a “green” solvent under mild reaction conditions.

  利用正式的逆直接芳香化策略，展示了高对位选择性的钯催化苯酚与芳基碘化物的直接芳香化反应。采用水作为“绿色”溶剂，在温和的反应条件下合成了一系列4-芳基苯酚。
• Photocatalyst-Free Visible-Light Photoredox Dearomatization of Phenol Derivatives Containing Ketoximes: An Easy Access to Spiropyrrolines
  作者：Yongzhen Han、Yunhe Jin、Min Jiang、Haijun Yang、Hua Fu

  DOI：10.1021/acs.orglett.9b00372

  日期：2019.3.15

  A novel and simple visible-light photoredox intramolecular dearomatization of phenol derivatives containing ketoximes leading to spiropyrrolines has been developed. The protocol uses readily available 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as the base and electron-donor, visible light as the light source, and the reaction was performed well at room temperature without need of a photocatalyst. Therefore

  已经开发出新颖且简单的可见光光氧化还原分子内脱芳香化作用的含酮肟的苯酚衍生物，从而导致螺吡咯啉。该方案使用现成的1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）作为碱和电子给体，可见光作为光源，该反应在室温下进行得很好，不需要光催化剂。因此，本方法应提供合成螺吡咯啉的有用策略。
• PIFA-Mediated Dearomatizative Spirocyclization of Phenolic Biarylic Ketones via Oxidation and C–C Bond Cleavage
  作者：Gui-Hua Zhao、Bi-Qing Li、Shuang-Shuang Wang、Man Liu、Yuan Chen、Bin Wang

  DOI：10.1021/acs.joc.0c00971

  日期：2020.7.17

  The dearomatizing spirocyclization of phenolic biarylic ketones using PhI(OCOCF3)2 as oxidant is presented. The reaction affords various cyclohexadienones through C–C bond cleavage under mild conditions. Mechanistic investigations reveal that an exocyclic enol ether acts as the key intermediate in the transformation.

  提出了以PhI（OCOCF 3）2为氧化剂的酚二芳基酮的脱芳香环化。该反应在温和条件下通过C–C键裂解提供各种环己二酮。机理研究表明，环外烯醇醚是转化的关键中间体。
• Asymmetric synthesis of spirocyclic isobenzofuranones <i>via</i> a squaramide-catalysed sulfa-Michael desymmetrisation reaction
  作者：Tamanna、Deepak Sharma、Pankaj Chauhan

  DOI：10.1039/d3ob00126a

  日期：——

  Enantioselective synthesis of spirocyclohexenone isobenzofuranones has been achieved through an organocatalysed sulfa-Michael desymmetrisation reaction. A cinchona-derived squaramide effectively promotes the desymmetrisation of spirocyclic 2,5-cyclohexadienone isobenzofuranones via the controlled addition of various aryl thiols to generate two vicinal stereocenters with perfect diastereoselectivities

  通过有机催化的磺胺-迈克尔去对称反应实现了螺环己烯酮异苯并呋喃酮的对映选择性合成。金鸡纳衍生的 squaramide通过控制添加各种芳基硫醇，有效促进螺环 2,5-环己二烯酮异苯并呋喃酮的去对称化，从而产生两个具有完美非对映选择性和非常好的对映选择性的邻位立构中心。