3-(3-hydroxyphenyl)propionitrile | 23941-88-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-(3-hydroxyphenyl)propionitrile
• 英文别名: 3-(3-hydroxyphenyl)propiononitrile；3-(3-hydroxyphenyl)propanenitrile；β--propionitril
• CAS: 23941-88-0
• 化学式: C₉H₉NO
• 分子量: 147.177
• InChiKey: WKUNJVDLRFNPBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(3-hydroxyphenyl)propionitrile 在 sodium azide 、 偶氮二甲酸二异丙酯 、 氯化铵 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 5-(3-(2,6-dimethylbenzyloxy)phenethyl)-1H-tetrazole
  参考文献：
  名称：

  TETRAZOLE COMPOUNDS FOR REDUCING URIC ACID

  摘要：

  公开号：

  EP2282736B1
• 作为产物：
  描述：

  间甲氧基苯乙基溴 在 三溴化硼 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 3-(3-hydroxyphenyl)propionitrile
  参考文献：
  名称：

  TETRAZOLE COMPOUNDS FOR REDUCING URIC ACID

  摘要：

  公开号：

  EP2282736B1

文献信息

• Design, synthesis and biological evaluation of 8-(2-amino-1-hydroxyethyl)-6-hydroxy-1,4-benzoxazine-3(4H)-one derivatives as potent β2-adrenoceptor agonists
  作者：Ce Yi、Gang Xing、Siqi Wang、Xiaoran Li、Yichuang Liu、Jinyan Li、Bin Lin、Anthony Yiu-Ho Woo、Yuyang Zhang、Li Pan、Maosheng Cheng

  DOI：10.1016/j.bmc.2019.115178

  日期：2020.1

  β2-adrenoceptor agonists with an 8-(2-amino-1-hydroxyethyl)-6-hydroxy-1,4-benzoxazine-3(4H)-one moiety is presented. The stimulatory effects of the compounds on human β2-adrenoceptor and β1-adrenoceptor were characterized by a cell-based assay. Their smooth muscle relaxant activities were tested on isolated guinea pig trachea. Most of the compounds were found to be potent and selective agonists of the β2-adrenoceptor

  提出了一系列具有2-（1-氨基-1-羟乙基）-6-羟基-1,4-苯并恶嗪-3（4H）-一个部分的β2-肾上腺素受体激动剂。通过基于细胞的测定来表征化合物对人β2-肾上腺素能受体和β1-肾上腺素能受体的刺激作用。在分离的豚鼠气管上测试了它们的平滑肌松弛活性。发现大多数化合物是β2-肾上腺素能受体的有效和选择性激动剂。其中一种化合物（R）-18c具有很强的β2-肾上腺素受体激动作用，EC50值为24 pM。它产生了与奥洛他特罗相同的充分而有效的气道平滑肌松弛作用。在体外豚鼠气管支气管扩张模型中，它的起效时间为3.5分钟，作用时间超过12小时。
• Synthesis of 8-Hydroxyquinolines by the Cyclization of<i>m</i>-Hydroxyphenethyl Ketone<i>O</i>-2,4-Dinitrophenyloximes
  作者：Katsuya Uchiyama、Yujiro Hayashi、Koichi Narasaka

  DOI：10.1055/s-1997-6146

  日期：1997.6

  8-Hydroxyquinolines are synthesized from O-2,4-dinitrophenyloximes of m-hydroxyphenethyl ketones by the treatment with sodium hydride, and then with 2,3-dichloro-4,5-dicyano-p-benzoquinone (DDQ).

  8-羟基喹啉是通过将m-羟基苯乙酮的O-2,4-二硝基苯肟与氢化钠处理，然后再与2,3-二氯-4,5-二氰基对苯醌（DDQ）反应合成的。
• Regioselective Synthesis of Quinolin-8-ols and 1,2,3,4-Tetrahydroquinolin-8-ols by the Cyclization of 2-(3-Hydroxyphenyl)ethyl Ketone<i>O</i>-2,4-Dinitrophenyloximes
  作者：Katsuya Uchiyama、Ayako Ono、Yujiro Hayashi、Koichi Narasaka

  DOI：10.1246/bcsj.71.2945

  日期：1998.12

  Cyclization of 2-(3-hydroxyphenyl)ethyl ketone O-2,4-dinitrophenyloximes proceeds on the oxime nitrogen atom by the treatment with NaH and then with 2,3-dichloro-5,6-dicyano-p-benzoquinone and acetic acid to yield quinolin-8-ols regioselectively. The reaction in the presence of Na[BH3(CN)] affords 1,2,3,4-tetrahydroquinolin-8-ols. The present cyclization proceeds via alkylideneaminyl radical intermediates

  2-(3-羟基苯基)乙基酮 O-2,4-二硝基苯基肟的环化反应在肟氮原子上进行，先用 NaH 处理，然后用 2,3-二氯-5,6-二氰基-对苯醌和乙酸处理区域选择性地产生喹啉-8-醇。在 Na[BH3(CN)] 存在下反应得到 1,2,3,4-四氢喹啉-8-醇。本环化通过亚烷基亚胺基自由基中间体进行，该中间体由 3-羟基苯基和 2,4-二硝基苯基部分之间的单电子转移产生。
• Novel dihydrochalcone sweetener compositions
  申请人：The Procter & Gamble Company

  公开号：US03932678A1

  公开（公告）日：1976-01-13

  A novel artificial sweetener compound, 3-(m-hydroxyphenyl)phloropropiophenone and a process for preparing same, as well as other 3-arylphloropropiophenones, from aryl aldehydes and phloroglucinol.

  一种新型的人工甜味剂化合物，3-(m-羟基苯基)苯丙酮，以及其制备方法，还包括从芳香醛和邻苯三酚制备其他3-芳基苯丙酮。
• Tetrazole compounds for reducing uric acid
  申请人：O'Neil James Dennen

  公开号：US08410154B2

  公开（公告）日：2013-04-02

  Uric acid in mammalian subjects is reduced and excretion of uric acid is increased by administering a compound of Formula I. The uric acid-lowering effects of the compounds of this invention are used to treat or prevent a variety of conditions including gout, hyperuricemia, elevated levels of uric acid that do not meet the levels customarily justifying a diagnosis of hyperuricemia, renal dysfunction, kidney stones, cardiovascular disease, risk for developing cardiovascular disease, tumor-lysis syndrome, cognitive impairment, early-onset essential hypertension, and Plasmodium falciparum-induced inflammation. In Formula 1, x is 1 or 2: y is O, 1, 2 or 3; and R1 is selected from the group consisting of hydrogen, alkyl having 1 or 2 carbon atoms, hydroxy, alkoxy having 1 or 2 carbon atoms, fluoro, chloro, bromo, and amino. A is phenyl unsubstituted or substituted by one, two or three groups selected from the group consisting of halo, alkyl having 1 or 2 carbon atoms, perfluoromethyL alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy; or cycloalkyl having from 3 to 6 ring atoms wherein the cycloalky! is unsubstituted or one one two ring carbons are independently mono-substituted by methyl or ethyl; or a 5 or 6 membered heleraromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon.

  通过给予化合物I，哺乳动物主体中的尿酸降低并且尿酸的排泄增加。该发明的化合物的降尿酸效果用于治疗或预防各种疾病，包括痛风、高尿酸血症、尿酸水平升高但不符合通常诊断为高尿酸血症的水平、肾功能障碍、肾结石、心血管疾病、发生心血管疾病的风险、肿瘤溶解综合症、认知障碍、早发性原发性高血压和疟原虫引起的炎症。在公式1中，x为1或2：y为O，1，2或3；R1选自羟基、1或2个碳原子的烷基、1或2个碳原子的烷氧基、氟、氯、溴和氨基的群组；A是苯基，未取代或被一个、两个或三个来自卤族、1或2个碳原子的烷基、1或2个碳原子的全氟甲基烷氧基和全氟甲氧基的群组或有3到6个环原子的环烷基，其中环烷基未取代或一个或两个环碳原子单独被甲基或乙基单取代；或有1或2个来自N、S和O的环杂原子的5或6元杂环芳烃环，并且杂芳环通过一个环碳原子与化合物的其余部分共价结合。