2,4-二甲基-8-羟基喹啉 | 115310-98-0

• 物质功能分类: 医药中间体 - 杂环化合物 - 喹啉类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 2,4-二甲基-8-羟基喹啉
• 英文名称: 2,4-dimethylquinolin-8-ol
• 英文别名: 8-hydroxy-2,4-dimethylquinoline；2,4-Dimethyl-8-hydroxyquinoline
• CAS: 115310-98-0
• 化学式: C₁₁H₁₁NO
• mdl: MFCD09743812
• 分子量: 173.214
• InChiKey: UXFZNPGAWHMSRK-UHFFFAOYSA-N

物化性质

• 熔点：
  64-66 °C
• 沸点：
  303.86°C (rough estimate)
• 密度：
  1.0898 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933499090
• 包装等级：
  III
• 危险类别：
  8
• 危险性防范说明：
  P264,P270,P280,P301+P312,P305+P351+P338,P310,P330,P501
• 危险品运输编号：
  1759
• 危险性描述：
  H302,H318
• 储存条件：
  室温

制备方法与用途

化学性质：淡黄色固体

反应信息

• 作为反应物：
  描述：

  2,4-二甲基-8-羟基喹啉 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-[(3-Bromomethyl-4-chloro-2-methoxyphenyl)sulfonyl]-L-proline methyl ester
  参考文献：
  名称：

  N-benzenesulphonyl-L-proline derivatives as bradykinin B.sub.2

  摘要：

  从由式(I)的化合物组成的化合物组中选择的化合物，其中X.sub.1和X.sub.2中的每一个（它们相同或不同）是卤素或C.sub.1-3烷氧基，R.sub.1是H、CF.sub.3或C.sub.1-3烷基，R.sub.2是氢原子或OH基团，A是(a)、(b)或(c)基团，B是单键，-CO-，-CO-CH.sub.2-，-CO-CH.sub.2-O-，-CO-CH.dbd.CH或-SO.sub.2-，m为2或3，N为0、1、2或3，R.sub.3为氢原子或甲基基团，W为CH或N，芳环上的酰胺基团C(.dbd.NR.sub.2)NH.sub.2位于2、3或4位，及其加合盐。公开了制备所述化合物的方法，以及其治疗用途，特别用于治疗涉及激肽酶的疾病。

  公开号：

  US06071917A1
• 作为产物：
  描述：

  4-(3-羟基苯基)-2-戊酮 在 盐酸 、 sodium hydride 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 23.0h， 生成 2,4-二甲基-8-羟基喹啉
  参考文献：
  名称：

  Design and Synthesis of Novel Sulfonamide-Containing Bradykinin hB₂ Receptor Antagonists. 1. Synthesis and SAR of α,α-Dimethylglycine Sulfonamides

  摘要：

  We recently published the extensive in vivo pharmacological characterization of MEN 16132 (J. Pharmacol. Exp. Ther. 2005, 616- 623; Eur. J. Pharmacol. 2005, 528, 7), a member of the sulfonamide-containing human B-2 receptor (hB(2)R) antagonists. Here we report, in detail, how this family of compounds was designed, synthesized, and optimized to provide a group of products with subnanomolar affinity for the hB2R and high in vivo potency after topical administration to the respiratory tract. The series was designed on the basis of indications from the X-ray structures of the key structural motifs A and B present in known antagonists and is characterized by the presence of an alpha,alpha-dialkyl amino acid. The first lead ( 17) of the series was submitted to extensive chemical work to elucidate the structural requirements to increase hB(2) receptor affinity and antagonist potency in bioassays expressing the human B2 receptor ( hB2R). The following structural features were selected: a 2,4-dimethylquinoline moiety and a piperazine linker acylated with a basic amino acid. The representative lead compound 68 inhibited the specific binding of [H-3] BK to hB(2)R with a pKi of 9.4 and antagonized the BK-induced inositolphosphate (IP) accumulation in recombinant cell systems expressing the hB(2)R with a pA(2) of 9.1. Moreover, compound 68 when administered (300 nmol/kg) intratracheally in the anesthetized guinea pig, was able to significantly inhibit BK-induced bronchoconstriction for up to 120 min after its administration, while having a lower and shorter lasting effect on hypotension.

  DOI：

  10.1021/jm060137l
• 作为试剂：
  描述：

  4-(3-bromomethyl-2,4-dichloro-benzenesulfonylamino)-tetrahydro-pyran-4-carboxylic acid methyl ester 、 2,4-二甲基-8-羟基喹啉 在 2,4-二甲基-8-羟基喹啉 作用下， 生成 4-[2,4-dichloro-3-(2,4-dimethyl-quinolin-8-yloxymethyl)-benzenesulfonylamino]-tetrahydropyran-4-carboxylic acid methyl ester
  参考文献：
  名称：

  J. Med. Chem. 2007, 50, 550-565

  摘要：

  DOI：

文献信息

• Pyridopyrimidones, quinolines and fused N-heterocycles as bradykinin
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US05994368A1

  公开（公告）日：1999-11-30

  This invention relates to a compound of the formula: ##STR1## wherein Z is a group of the formula: ##STR2## in which X.sup.1 is N or C--R.sup.1, X.sup.2 is N or C--R.sup.9, X.sup.3 is N or C--R.sup.2, R.sup.1 is lower alkyl, R.sup.2 is hydrogen, lower alkyl, etc., R.sup.9 is hydrogen or lower alkyl, R.sup.3 is halogen, etc., R.sup.4 is halogen, etc., R.sup.5 is a group of the formula: ##STR3## A is lower alkylene, and Y is O, etc., and pharmaceutically acceptable salts thereof, to processes for preparation thereof, to a pharmaceutical composition comprising the same, and to methods to using the same therapeutically in the prevention and/or the treatment of bradykinin or its analogues mediated diseases in human being or animals.

  这项发明涉及以下化合物的公式：##STR1## 其中 Z 是以下公式的一个基团：##STR2## 其中 X^1 是 N 或 C--R^1，X^2 是 N 或 C--R^9，X^3 是 N 或 C--R^2，R^1 是较低的烷基，R^2 是氢，较低的烷基等，R^9 是氢或较低的烷基，R^3 是卤素等，R^4 是卤素等，R^5 是以下公式的一个基团：##STR3## A 是较低的烷基，Y 是 O 等，以及其药学上可接受的盐，制备方法，包含相同化合物的药物组合物，以及在人类或动物中在预防和/或治疗激肽酶或其类似物介导的疾病中治疗使用相同的方法。
• Theoretical and experimental studies on the fluorescence properties of aluminum(III), cadmium(II), zinc(II), and copper(II) complexes of substituted 8-hydroxyquinoline
  作者：Zhang Yuanyuan、Cheng Hongrui、Sun Qingrong、Chen Hongli、Yang Weiqing、Ma Menglin

  DOI：10.1177/1747519820973601

  日期：2021.5

  Fifty-five 8-hydroxyquinoline (8-HQ) derivatives are synthesized and the corresponding aluminum(III), cadmium(II), copper(II), and zinc(II) metal complexes are prepared and their fluorescent activi...

  合成了55种8-羟基喹啉（8-HQ）衍生物并制备了相应的铝（III）、镉（II）、铜（II）和锌（II）金属配合物及其荧光活性...
• Study on Relationship Between Fluorescence Properties and Structure of Substituted 8-Hydroxyquinoline Zinc Complexes
  作者：He Jianbo、Zhou Tingting、Cao Yongjing、Zhang Yuanyuan、Yang Weiqing、Ma Menglin

  DOI：10.1007/s10895-018-2275-7

  日期：2018.9

  at the same time, blue-shifted of fluorescence emission wavelength was observed when the C-5 position of 8-hydroxyquinoline was substituted by electron-withdrawing group. When the C-4 position of 8-hydroxyquinolie was substituted by methyl or the C-5 position was substituted by sulfonic acid group, the corresponding zinc complexes had higher fluorescence intensity than 8-hydroxyquinolie zinc.

  由8-羟基喹啉金属络合物生产的有机发光二极管（OLED）在现代电致发光器件中起着至关重要的作用。本文采用不同的方法合成了一系列的8-羟基喹啉衍生物，并制备了相应的锌金属配合物。测量了配合物的紫外和荧光性质，旨在了解喹啉环上的取代基对配合物的荧光性质的影响。当8-羟基喹啉的C-5被卤素取代时，荧光发射波长发生了红移，同时，当8-羟基喹啉的C-5位置为2时，观察到荧光发射波长发生了蓝移。被吸电子基团取代。
• Preparation and Characterization of Tow kinds of cis-(RuCl(qn)2NO) (Hqn=4-Methyl-, 2,4-dimetyl-, 2-ethly-, or 5-chloro-8-quinolinol), and the Photoinduced Preparation of the trans-(RuCl(qn)2NO) from the cis-Complex.
  作者：Hidenori Ikezawa、Eiichi Miki、Kunihiko Mizumachi、Tatujiro Ishimori、Takashi Nagai、Mikio Tanaka

  DOI：10.1246/bcsj.66.89

  日期：——

  A mixture of hydrous trichloronitrosylruthenium(III) and 8-qulinolinol derivative (4-methyl-, 2,4-dimethyl-, 2-ethyl-, or 5-chloro-8-quinolinol) (mole ratio 1 : 4—5) was refluxed in ethyl alcohol in the dark to prepare two kinds of cis-type complexes, [RuCl(qn)2NO] (Hqn = 8–quinolinol derivative), cis-1 and cis-2, as major products. Using 2,4-dimethyl- or 2-ethyl-8-quinolinol, the trans complex was prepared in low yield with the cis-type complexes. The trans complex could be photochemically generated from the cis-1 complex in dichloromethane in good yield. The introduction of an alkyl group with an electrondonating nature to the 2-position in the quinolinol ring could induce the formation of the trans complex. The complexes were characterized by NMR, IR UV-vis, and field desorption mass spectrometries. From the cis-1-trans photoisomerization reaction in the presence of 15NO (15N atom % = 99), a bond rupture between Ru and NO was found to be involved in the reaction.

  将水合三氯硝基铑(III)与8-喹啉醇衍生物（4-甲基、2,4-二甲基、2-乙基或5-氯-8-喹啉醇）以1:4-5的摩尔比在黑暗中用乙醇重流反应，制备了两种顺式配合物[RuCl(qn)2NO]（Hqn = 8-喹啉醇衍生物），主要产品为顺式-1和顺式-2。使用2,4-二甲基或2-乙基-8-喹啉醇，可以在低产率下与顺式配合物一起制备反式配合物。反式配合物可以通过光化学反应从顺式-1配合物中在二氯甲烷中以较高产率生成。向喹啉醇环的2位引入具有供电子性质的烷基团可以诱导反式配合物的形成。这些配合物通过核磁共振（NMR）、红外光谱（IR）、紫外-可见光谱（UV-vis）和场解吸质谱（field desorption mass spectrometries）进行了表征。通过含有15NO（15N原子百分比=99）的顺式-1与反式光异构化反应发现，反应中涉及铑与NO之间的键断裂。
• 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。