4-hydroxyphenyl 3-methoxyphenyl methanone | 72090-62-1

• 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: 4-hydroxyphenyl 3-methoxyphenyl methanone
• 英文别名: 4'-Hydroxy-3-methoxybenzophenone；3-Methoxy-4'-hydroxy-benzophenon；4-Hydroxy-3'-methoxybenzophenon；(4-Hydroxyphenyl)-(3-methoxyphenyl)methanone
• CAS: 72090-62-1
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: USYZLABLTLYZKW-UHFFFAOYSA-N

物化性质

• 熔点：
  141–142°C
• 沸点：
  417.6±30.0 °C(Predicted)
• 密度：
  1.201±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-hydroxyphenyl 3-methoxyphenyl methanone 在 sodium hydride 、 氨基磺酰氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Sulfamic acid 4-(3-methoxy-benzoyl)-phenyl ester
  参考文献：
  名称：

  4,4′-Benzophenone-O,O′-disulfamate: a potent inhibitor of steroid sulfatase

  摘要：

  We investigated whether the benzophenone moiety can be used as core element of steroid sulfatase (STS) inhibitors. While 4- and 3-benzophenone-O-sulfamates inhibit STS with IC50 values between 5 and 7 muM irrespective of additional hydroxy and methoxy substituents at the second phenyl ring, benzophenone-O,O'-disulfamates show increased activity. With an IC50 value of 190nM the 4,4'-derivative is the first small monocyclic STS inhibitor coming close to the potency of the steroidal standard estrone sulfamate. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00381-5
• 作为产物：
  描述：

  4-[(叔-丁基二甲基甲硅烷)氧代]苯甲醛 在 manganese(IV) oxide 、 正丁基锂 、 氢氟酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 3.0h， 生成 4-hydroxyphenyl 3-methoxyphenyl methanone
  参考文献：
  名称：

  4,4′-Benzophenone-O,O′-disulfamate: a potent inhibitor of steroid sulfatase

  摘要：

  We investigated whether the benzophenone moiety can be used as core element of steroid sulfatase (STS) inhibitors. While 4- and 3-benzophenone-O-sulfamates inhibit STS with IC50 values between 5 and 7 muM irrespective of additional hydroxy and methoxy substituents at the second phenyl ring, benzophenone-O,O'-disulfamates show increased activity. With an IC50 value of 190nM the 4,4'-derivative is the first small monocyclic STS inhibitor coming close to the potency of the steroidal standard estrone sulfamate. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00381-5

文献信息

• Benzophenone Derivatives and Related Compounds as Potent Histamine H3-Receptor Antagonists and Potential PET/SPECT Ligands
  作者：Astrid Sasse、Xavier Ligneau、Bassem Sadek、Sigurd Elz、Heinz H. Pertz、C. Robin Ganellin、Jean-Michel Arrang、Jean-Charles Schwartz、Walter Schunack、Holger Stark

  DOI：10.1002/1521-4184(200102)334:2<45::aid-ardp45>3.0.co;2-2

  日期：2001.2

  Para‐substituted aromatic ethers with benzophenone or related structural elements and a 3‐(1H‐imidazol‐4‐yl)propyloxy moiety were prepared by Mitsunobu‐type ether synthesis or SNAr reaction. Most of the title compounds possess high antagonist potency in histamine H3‐receptor assays in vitro as well as in vivo in mouse CNS following oral administration. After defining 4‐(3‐(1H‐imidazol‐4‐yl)propyloxy)phenyl

  通过Mitsunobu型醚合成或SNAr反应制备了具有二苯甲酮或相关结构元素和3-(1H-咪唑-4-基)丙氧基部分的对位取代芳族醚。大多数标题化合物在口服给药后的小鼠 CNS 体外和体内组胺 H3 受体测定中具有高拮抗剂效力。将 4-(3-(1H-咪唑-4-基)丙氧基)苯基苯基甲酮定义为新的先导化合物后，研究了这类新化合物的构效关系。用卤素原子（例如碘、氟）取代二苯甲酮部分的间'位导致化合物在体外和体内具有高拮抗剂效力（Ki = 9.3 和 4.3 nM，ED50 = 0.7 和 0.47 mg/ kg po，分别为 18 和 12）。
• Modulators of peroxisome proliferator activated receptors
  申请人：Brooks Alisa Dawn

  公开号：US20050020684A1

  公开（公告）日：2005-01-27

  Disclosed is a compound represented by Structural Formula (I): Ar is a substituted or unsubstituted aromatic group. Q is a covalent bond, —CH 2 — or —CH 2 CH 2 —; W is a substituted or unsubstituted alkylene or a substituted or unsubstituted heteroalkylene linking group from two to ten atoms in length, preferably from two to seven atoms in length. Phenyl Ring A is optionally substituted with up to four substituents in addition to R 1 and W, R 2 is (CH 2 ) n —CH(OR 2 )—(CH 2 ) n E, —(CH)═C(OR 2 )—(CH 2 ) n E, —(CH 2 ) n —CH(Y)—(CH 2 ) m E or (CH)═C(Y)(CH 2 ) m E; wherein E is COOR 3 , C 1 -C 3 alkylnitrile, carboxamide, sulfonamide, acylsulfonamide or tetrazole and wherein sulfonamide, acylsulfonamide and tetrazole are optionally substituted with one or more substituents independently selected from: C 1 -C 6 alkyl, haloalkyl and aryl-C o - 4 -alkyl; R 2 is H, an aliphatic group, a substituted aliphatic group, haloalkyl, an aromatic group, a substituted aromatic group, —COR 4 , —COOR 4 , —CONR 5 R 6 , —C(S)R 4 , —C(S)OR 4 or C(S)NR 5 R 6 , R 3 is H, an aliphatic group, a substituted aliphatic group, an aromatic group or a substituted aromatic group. Y is O—, CH 2 —, CH 2 CH 2 — or CH═CH— and is bonded to a carbon atom in Phenyl Ring A that is ortho to R 1 . R 4 -R 6 are independently H, an aliphatic group, a substituted aliphatic group, an aromatic group or a substituted aromatic group. n and m are independently 0, 1 or 2.

  本发明公开了一种由结构式（I）表示的化合物：其中Ar是取代或未取代的芳香基团。Q是共价键，-CH2-或-CH2CH2-; W是取代或未取代的烷基或取代或未取代的异烷基连接基，长度为两到十个原子，优选长度为两到七个原子。苯环A可选地与R1和W以外的最多四个取代基取代，R2是（CH2）n-CH（OR2）-（CH2）nE，-（CH）=C（OR2）-（CH2）nE，-（CH2）n-CH（Y）-（CH2）mE或（CH）=C（Y）（CH2）mE;其中E是COOR3，C1-C3烷基腈，羧酰胺，磺酰胺，酰基磺酰胺或四唑，磺酰胺，酰基磺酰胺和四唑可选地与一个或多个取代基取代，独立地选自：C1-C6烷基，卤代烷基和芳基-Co-4-烷基; R2是H，脂肪基，取代脂肪基，卤代烷基，芳基，取代芳基，-COR4，-COOR4，-CONR5R6，-C（S）R4，-C（S）OR4或C（S）NR5R6，R3是H，脂肪基，取代脂肪基，芳基或取代芳基。Y是O-，CH2-，CH2CH2-或CH═CH-，并与Phenyl环A中与R1相邻的碳原子键合。R4-R6独立地是H，脂肪基，取代脂肪基，芳基或取代芳基。n和m独立地为0、1或2。
• Photocatalytic oxidative coupling of terminal alkynes with p-benzoquinone to diaryl ketones by the Cu(I)-PS-POM assembling system through synergistic effect
  作者：Ting Zhang、Jiachen Jiao、Kaixin Guo、Lei Zhang、Chuanbao Zhang、Qiuxia Han

  DOI：10.1016/j.jcat.2023.115287

  日期：2024.1

  3,5-triazine (TPT) and binuclear Cu(I) units. CuW–TPT exhibits excellent light absorption ability and unique conductivity due to the coordination bond, strong π∙∙∙π interactions and H-bonding among Cu(I) ions, TPT moieties and [WO] in the defined spatial. The abundant exposed Cu(I) catalytic centres are conductive to activate phenylacetylene in situ formation Cu(I)-phenylacetylide, which then undergoes

  光催化C-C键形成是合成重要药物中间体二芳基酮的有效方法。在此，通过将氧化催化剂[WO]组装到由光敏剂（PS）4,6-三（4-吡啶基）-1构建的光活性MOF中，合成了一种新的基于多金属氧酸盐的金属有机框架（POMOF）CuW-TPT。 ,3,5-三嗪 (TPT) 和双核 Cu(I) 单元。由于Cu(I)离子、TPT部分和[WO]在特定空间内的配位键、强π∙∙∙π相互作用和H键，CuW-TPT表现出优异的光吸收能力和独特的电导率。丰富的暴露的Cu(I)催化中心有利于激活苯乙炔原位形成Cu(I)-苯乙酰化物，然后经过还原单电子转移(SET)过程得到Paterno的关键中间体Cu(II)-苯乙化物-Buchi (2+2) 与苯醌环加成形成不稳定的 Cu(II)-氧杂环丁烷环。它是从简单的起始原料（例如末端炔烃与对苯醌）合成带有羟基的二芳基酮的直接路线。
• Regioselectivity in the Alkaline Thiolate Deprotection of Aryl Methyl Ethers
  作者：Jeffrey A. Dodge、Mark G. Stocksdale、Kennan J. Fahey、C. David Jones

  DOI：10.1021/jo00108a046

  日期：1995.2
• MODULATORS OF PEROXISOME PROLIFERATOR ACTIVATED RECEPTORS
  申请人：ELI LILLY AND COMPANY

  公开号：EP1392637A2

  公开（公告）日：2004-03-03