(2-hydroxy-5-methylphenyl)(p-tolyl)methanone | 26880-95-5

• 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-hydroxy-5-methylphenyl)(p-tolyl)methanone
• 英文别名: (4-methylphenyl)(2-hydroxy-5-methylphenyl)methanone；Methanone, (2-hydroxy-5-methylphenyl)(4-methylphenyl)-；(2-hydroxy-5-methylphenyl)-(4-methylphenyl)methanone
• CAS: 26880-95-5
• 化学式: C₁₅H₁₄O₂
• 分子量: 226.275
• InChiKey: BMISHCBZAGNESL-UHFFFAOYSA-N

物化性质

• 熔点：
  89.5–90°C
• 沸点：
  371.1±30.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  (2-hydroxy-5-methylphenyl)(p-tolyl)methanone 在 氢氧化钾 、 potassium carbonate 、 一水合肼 作用下， 以 甲醇 、 乙醇 、 丙酮 为溶剂， 反应 17.0h， 生成 [5-methyl-2-[(2-thioxo-3H-1,3,4-oxadiazol-5-yl)methoxy]phenyl]-(p-tolyl)methanone
  参考文献：
  名称：

  Synthesis and antimicrobial study of novel heterocyclic compounds from hydroxybenzophenones

  摘要：

  The triazolothiadiazine analogues 6a-e were obtained via a multistep synthesis sequences beginning with the hydroxybenzophenones la-e. Hydroxybenzophenones on reaction with ethyl chloroacetate affords ethyl (2-aroylarytoxy)acetates 2a-e which on treatment with hydrazine hydrate yields 2-(2-aroylaryloxy)acetohydrazides 3a-e. Intramolecular cyclization of 3a-e with carbon disulfide affords 5-(2-aroylaryloxy)methyl-1,3,4-oxadiazole-2-(3H)thiones 4a-e, which on treatment with hydrazine hydrate yields 4-amino-5-(2-aroyl aryloxy)methyl-1,2,4-triazole-3-(2H)thiones 5a-e. Condensation of 5a-e with alpha-halocarbonyl compound results in 3-(2-aroylaryloxy)methyl-6-phenyl-1,2,4-triazolo[3,4-b][1,3,4] thiadiazine 6a-e analogues. The compounds 4a-e, 5a-e and 6a-e were tested against variety of fungal and bacterial strains in comparison to fluconazole and chloramphenicol, respectively. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.04.005
• 作为产物：
  描述：

  苯甲酸-4-甲基苯酯 在 盐酸 、 三氯化铝 、 溴 作用下， 反应 10.0h， 生成 (2-hydroxy-5-methylphenyl)(p-tolyl)methanone
  参考文献：
  名称：

  Montfort, Bernard; Laude, Bernard; Vebrel, Joel, Bulletin de la Societe Chimique de France, 1987, # 5, p. 848 - 854

  摘要：

  DOI：

文献信息

• Synthesis and tumor inhibitory activity of novel coumarin analogs targeting angiogenesis and apoptosis
  作者：B.R. Vijay Avin、Prabhu Thirusangu、V. Lakshmi Ranganatha、Aiyesha Firdouse、B.T. Prabhakar、Shaukath Ara Khanum

  DOI：10.1016/j.ejmech.2014.01.050

  日期：2014.3

  A sequence of coumarin analogs 5a–j was obtained by multi step synthesis from hydroxy benzophenones (1a–j). The in vitro antiproliferative effect of the title compounds was tested against Ehrlich ascites carcinoma (EAC) and Daltons lymphoma ascites (DLA) cell lines. Among the series, compound 5c with bromo group in the benzophenone moiety was endowed with excellent antiproliferative potency with significant

  通过多步合成从羟基二苯甲酮（1a – j）获得了香豆素类似物5a – j的序列。在体外的标题化合物的抗增殖作用是对艾氏腹水癌（EAC）和道尔顿淋巴瘤腹水（DLA）细胞系进行测试。在该系列中，在二苯甲酮部分中具有溴基的化合物5c具有出色的抗增殖潜能，IC 50值很高。此外，化合物5c对鼠EAC和实体DL肿瘤模型系统的体内抗肿瘤作用通过延长的存活期得到证实。复方的抑瘤机制5c是由于抗血管生成和促进细胞凋亡。这些结果表明化合物5c的可能应用，其可以在不久的将来被开发为有效的抗癌药。
• Operationally Simple and Selective One-Pot Synthesis of Hydroxyphenones: A Facile Access to SNARF Dyes
  作者：Rainer Mahrwald、Celin Richter、Nikolaus Ernsting

  DOI：10.1055/s-0035-1561370

  日期：——

  observed during a Friedel–Crafts acylation/demethylation cascade. In contrast to this cascade, oxygen-containing acylating reagents do not undergo the demethylation step. By the methodology elaborated here, an access is provided to important intermediates for the total synthesis of seminaphthorhodafluor (SNARF) dyes. High selectivity is observed during a Friedel–Crafts acylation/demethylation cascade

  摘要 在Friedel-Crafts酰化/去甲基化级联反应中观察到高选择性。与该级联反应相反，含氧的酰化剂不进行脱甲基步骤。通过此处阐述的方法，可以为重要的中间体提供全萘四氟（SNARF）染料的全合成。 在Friedel-Crafts酰化/去甲基化级联反应中观察到高选择性。与该级联反应相反，含氧的酰化剂不进行脱甲基步骤。通过此处阐述的方法，可以为重要的中间体提供全萘四氟（SNARF）染料的全合成。
• Design, synthesis and molecular docking of benzophenone conjugated with oxadiazole sulphur bridge pyrazole pharmacophores as anti inflammatory and analgesic agents
  作者：Zabiulla、A.R. Gulnaz、Yasser Hussein Eissa Mohammed、Shaukath Ara Khanum

  DOI：10.1016/j.bioorg.2019.103220

  日期：2019.11

  active lipid compounds having diverse hormone like effects are important mediators of the body’s response to pain and inflammation, and are formed from essential fatty acids found in cell membranes. This reaction is catalyzed by cyclooxygenase, a membrane associated enzyme occurring in two isoforms, COX-1 and COX-2. Nonsteroidal anti-inflammatory drugs (NSAIDs) act by inhibiting the activity of COX.

  前列腺素（PG）是一组具有多种激素样作用的生理活性脂质化合物，是人体对疼痛和炎症反应的重要介体，由细胞膜中的必需脂肪酸形成。该反应由环氧合酶催化，环氧合酶是一种与膜相关的酶，以两种同工型COX-1和COX-2发生。非甾体类抗炎药（NSAIDs）通过抑制COX的活性发挥作用。鉴于此，设计，合成，表征并随后评价了与恶二唑硫桥吡唑部分8a-1缀合的一系列新型二苯甲酮的抗炎和镇痛特性。新型类似物8a-1的研究对潜在的抗炎活性显示出高水平的COX-1和COX-2抑制活性。在该系列中，化合物8i在二苯甲酮的苯甲酰基环的对位具有吸电子氟基团，其特征在于对COX-1和COX-2的抑制均具有最高的IC 50值，这与标准药物相当。此外，已经对有效化合物进行了分子对接研究。
• Eco-friendly organocatalyst- and reagent-controlled selective construction of diverse and multifunctionalized 2-hydroxybenzophenone frameworks for potent UV-A/B filters by cascade benzannulation
  作者：Muhammad Saeed Akhtar、Raju S. Thombal、Ramuel John Inductivo Tamargo、Won-Guen Yang、Sung Hong Kim、Yong Rok Lee

  DOI：10.1039/d0gc01011a

  日期：——

  2-hydroxy-3′-formylbenzophenones and [4 + 2] cycloaddition for 2-hydroxybenzophenones. With this methodology, an unprecedented double benzannulation allows one-pot construction of diverse 7-(2′-hydroxybenzoyl)-2-naphthaldehydes via [3 + 3 + 4] cycloaddition. This protocol features a broad substrate scope, high functional-group tolerance, and operational simplicity in an environmentally benign green solvent

  在绿色下，由有机催化剂和试剂控制的高选择性合成各种功能化的新型2-羟基二苯甲酮骨架，例如2-羟基-3'-甲酰基二苯甲酮，7-（2'-羟基苯甲酰基）-2-萘醛和2-羟基二苯甲酮描述了开发有效的UV-A / B滤光片的条件。有机催化的苯环化反应分别通过[3 + 3]环加成反应进行2-羟基-3'-甲酰基二苯甲酮的合成，以及[4 + 2]环加成反应进行2-羟基二苯甲酮的合成。用这种方法，一个前所未有的双苯并环化允许一锅煮结构多样7-（2'-羟基苯甲酰基）-2-萘甲醛通过[3 + 3 + 4]环加成。该协议具有广泛的底物范围，高官能团耐受性和在环境友好的绿色溶剂中的操作简便性。合成的化合物已成功用于进一步转化，并已被很好地表征为有效的UV-A / B过滤剂。
• A facile synthesis of dihydrobenzofuranols by photocyclization of (2-alkoxy-5-methyl-phenyl)(aryl) methanone and ethyl 2-aroyl-4-methylphenyloxyacetates
  作者：S. Shashikanth、B. S. Sudha、S. A. Khanum

  DOI：10.1002/hc.20111

  日期：——

  acetonitrile underwent photocyclization to substituted dihydrobenzofuranols 3a–i with 3a–c in very less yield being racemate and 3d–i in good yield being mixture of cis-trans isomers showing high stereoselectivity in benzene and decreased stereoselectivity in acetonitrile. © 2005 Wiley Periodicals, Inc. Heteroatom Chem 16:212–217, 2005; Published online in Wiley InterScience (www.interscience.wiley.com). DOI

  2-烷氧基取代的二苯甲酮 2a-f 和 2-芳酰基-4-甲基苯氧基乙酸乙酯 2g-i 在苯和乙腈中的辐照经过光环化反应生成取代的二氢苯并呋喃醇 3a-i，其中 3a-c 的产率非常低，外消旋物和 3d-i 在顺反异构体混合物的产率良好，在苯中显示出高立体选择性，在乙腈中显示出立体选择性降低。© 2005 Wiley Periodicals, Inc. 杂原子化学 16:212–217, 2005; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20111