2-(4-hydroxyphenyl)-1-phenylethanone | 6420-90-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-(4-hydroxyphenyl)-1-phenylethanone
• 英文别名: (4-Hydroxybenzyl) phenyl ketone；2-(4-hydroxyphenyl)-1-phenylethan-1-one
• CAS: 6420-90-2
• 化学式: C₁₄H₁₂O₂
• 分子量: 212.248
• InChiKey: VCWCUMTYRJJXHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  2-(4-hydroxyphenyl)-1-phenylethanone 在 sodium hydroxide 作用下， 以 N-甲基乙酰胺 、 甲醇 、 正己烷 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 以82.4%的产率得到2-(4-羟基苯)丙酸
  参考文献：
  名称：

  Process for preparing phenylalkanoic acids

  摘要：

  羟基苯乙酸是通过对应的苯甲醛或烷基苯酮经过还原、氰化和水解而形成的，中间产物无需分离或纯化。

  公开号：

  US04415751A1
• 作为产物：
  描述：

  2,2-二氯苯乙酮 在 五甲基二乙烯三胺 、 copper(II) bis(trifluoromethanesulfonate) 、 碳酸氢钠 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 21.0h， 生成 2-(4-hydroxyphenyl)-1-phenylethanone
  参考文献：
  名称：

  Cu催化的烯酮的立体选择性γ-烷基化

  摘要：

  使用 α-卤代羰基化合物和二烯醇醚通过 Cu(II) 催化形成一般的区域选择性和立体选择性 γ-CC 键。这种方法构成了一种具有挑战性的 1,6-双加氧基序的新方法。一系列 γ 取代的烯酮，包括许多带有全碳四元中心的，可在温和的反应条件下通过简单的方案获得，并具有极好的官能团兼容性。观察到出色的立体诱导，提供对具有挑战性的立体化学阵列的受控访问。

  DOI：

  10.1021/jacs.6b02565

文献信息

• Palladium catalyzed addition of arylboronic acid or indole to nitriles: synthesis of aryl ketones
  作者：Tuluma Das、Amarnath Chakraborty、Amitabha Sarkar

  DOI：10.1016/j.tetlet.2014.11.009

  日期：2014.12

  Aryl ketones can be synthesized conveniently by a palladium catalyzed addition of arylboronic acid to nitriles in aqueous triflic acid. This catalytic system was extended to the addition of unprotected indoles to nitriles under a slightly modified condition to produce 3-acyl indoles in good yields.

  芳基酮可以通过在三氟甲磺酸水溶液中钯催化将芳基硼酸加成到腈中来方便地合成。该催化体系扩展到在稍加修饰的条件下向腈中加入未保护的吲哚，以高收率生产3-酰基吲哚。
• Structure-activity relationship of estrogens: receptor affinity and estrogen antagonist activity of certain (E)- and (2)-1,2,3-triaryl-2-propen-2-ones
  作者：Shubhra Mittal、Susheel Durani、Randhir S. Kapil

  DOI：10.1021/jm00382a019

  日期：1985.4

  (E)- and (Z)-1,2,3-triphenyl-2-propen-1-ones and some of their phenolic and alkoxy analogues, substituted at the para position in one or more of the aromatic rings, were synthesized and assigned geometry on the basis of their spectroscopic data. The structure-activity relationship of the triarylpropenones was studied from the point of view of their estrogen receptor affinity and estrogen agonist and antagonist activities. (E)- as well as (Z)-propenones were found to compete with estradiol for binding with the mouse uterine cytosol receptors, with phenolic analogues usually more potent than the unsubstituted as well as alkoxypropenones. The (E)-propenones, which have now emerged as a new group of estrogen receptor ligands, were found to differ from Z isomers quite markedly in their binding specificities. The uterotrophic and antiuterotrophic assays in immature mice revealed that while some of the compounds were marginally estrogenic, nearly all the isomeric propenones were antiestrogenic to a varying degree.

  (E)-和(Z)-1,2,3-三苯甲丙二烯酮及其酚类和醚类的类物在芳香环的para位被取代的情况下被合成了，这些化合物的立体结构是基于它们的光谱数据进行判断的。从雌激素受体亲和力以及雌激素亲和力的协同作用和拮抗作用的层面，探讨了丙三环酮的结构活性关系。无论是(E)-还是(Z)-的丙烯酮都与小鼠子宫细胞受体发生了竞争性的结合，酚类的类物通常比未取代的结构和醚类的丙烯酮有更强的亲和力。可以与雌激素结合的丙烯酮的身影作为新的雌激素受体配体逐渐浮现，但它们与(Z)-同分异构体在结合特异性方面有很大的不同。生胎性以及抑生胎性在幼鼠中的测试显示，虽然有些化合物具有微弱的雌激素性质，但几乎所有的同分异构体丙烯酮都具有一定程度的抑生胎性。
• Estrogen receptor modulators
  申请人：——

  公开号：US20030225132A1

  公开（公告）日：2003-12-04

  The present invention relates to compounds and derivatives thereof, their synthesis, and their use as estrogen receptor modulators. The compounds of the instant invention are ligands for estrogen receptors and as such may be useful for treatment or prevention of a variety of conditions related to estrogen functioning including: bone loss, bone fractures, osteoporosis, cartilage degeneration, endometriosis, uterine fibroid disease, hot flashes, increased levels of LDL cholesterol, cardiovascular disease, impairment of cognitive functioning, cerebral degenerative disorders, restenosis, gynecomastia, vascular smooth muscle cell proliferation, obesity, incontinence, and cancer, in particular of the breast, uterus and prostate.

  本发明涉及化合物及其衍生物，它们的合成以及它们作为雌激素受体调节剂的用途。本发明的化合物是雌激素受体的配体，因此可能对治疗或预防与雌激素功能相关的多种疾病条件有用，包括：骨质疏松、骨折、骨质疏松症、软骨退化、子宫内膜异位症、子宫肌瘤病、潮热、低密度脂蛋白胆固醇水平升高、心血管疾病、认知功能障碍、脑退行性疾病、再狭窄、男性乳房增大、血管平滑肌细胞增殖、肥胖、尿失禁和癌症，尤其是乳腺、子宫和前列腺癌。
• The tin(II) enolate addition reactions to α, β-unsaturated ketones and quinones
  作者：Teruaki Mukaiyama、Nobuharu Iwasawa、Takeshi Yura、R.S.J. Clark

  DOI：10.1016/s0040-4020(01)87679-1

  日期：1987.1

  The reaction of tin(II) enolates with various α ,β-unsaturated carbonyl compounds is examined. When TMSCl is added as an activator of the α,β-unsaturated ketones, the Michael addition reaction proceeds smoothly to give the corresponding 1,4-adduct in good yield. When 1,4-benzoquinone and its mono-imino derivative are employed as acceptors in conjunction with dichloromethylsilane- DMAP activator, a

  研究了锡（II）烯醇化物与各种α，β-不饱和羰基化合物的反应。当加入TMSCl作为α，β-不饱和酮的活化剂时，迈克尔加成反应顺利进行，以良好的产率得到相应的1，4-加合物。当将1，4-苯醌及其单亚氨基衍生物与二氯甲基硅烷-DMAP活化剂一起用作受体时，发生新的加成-还原反应以提供α-芳基羰基化合物。
• A Convenient Preparation of α-(<i>p</i>-Hydroxy- or<i>p</i>-Aminophenyl) Carbonyl Compounds. Addition–Reduction Reaction of Tin(II) Enolate with p-Benzoquinone and Its Mono-<i>N</i>-tosylimino Derivative
  作者：Teruaki Mukaiyama、Richard S. J. Clark、Nobuharu Iwasawa

  DOI：10.1246/cl.1987.479

  日期：1987.3.5

  Tin(II) enolates react with p-benzoquinone and its mono-N-tosylimino derivative to give 1,2-adducts in good yield. These can be reduced in situ to α-(p-hydroxy- or p-aminophenyl) carbonyl derivatives by addition of dichloromethylsilane and dimethylaminopyridine.

  锡 (II) 烯醇化物与对苯醌及其单-N-甲苯磺酰亚氨基衍生物反应，以良好的产率得到 1,2-加合物。通过加入二氯甲基硅烷和二甲氨基吡啶，这些可以原位还原为 α-（对羟基或对氨基苯基）羰基衍生物。