3-乙基-2-甲基喹啉-4-醇 | 1888-01-3

• 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: 3-乙基-2-甲基喹啉-4-醇
• 中文别名: 4-喹啉醇,3-乙基-2-甲基-
• 英文名称: 3-ethyl-2-methylquinolin-4-ol
• 英文别名: 2-Methyl-3-ethyl-4-hydroxychinolin；3-Aethyl-2-methyl-chinolin-4-ol；3-ethyl-2-methyl-1H-quinolin-4-one
• CAS: 1888-01-3
• 化学式: C₁₂H₁₃NO
• mdl: MFCD00461559
• 分子量: 187.241
• InChiKey: UUDYPKCYYIOUJD-UHFFFAOYSA-N

物化性质

• 熔点：
  275 °C(Solv: methanol (67-56-1))
• 沸点：
  327.7±37.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-乙基-2-甲基喹啉-4-醇 在 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以2.92 g的产率得到喹啉,4-氯-3-乙基-2-甲基-
  参考文献：
  名称：

  Structure−Activity Relationship of Quinoline Derivatives as Potent and Selective α_2C-Adrenoceptor Antagonists

  摘要：

  Starting from two acridine compounds identified in a high-throughput screening campaign (1 and 2, Table 1), a series of 4-aminoquinolines was synthesized and tested for their properties on the human alpha(2)-adrenoceptor subtypes (alpha(2A), alpha(2B), and alpha(2C.)). A number of compounds with good antagonist potencies against the alpha(2C)-adrenoceptor and excellent subtype selectivities over the other two subtypes were discovered. For example, (R)-{4-[4-(3,4-dimethylpiperazin-1-yl) phenylamino] quinolin- 3- yl} methanol 6j had an antagonist potency of 8.5 nM against, and a subtype selectivity of more than 200-fold for, the alpha(2C)-adrenoceptor. Investigation of the structure-activity relationship identified a number of structural features, the most critical of which was an absolute need for a substituent in the 3-position of the quinoline ring. The 3-position on the piperazine ring was also found to play an appreciable role, as substitutions in that position exerted a significant and stereospecific beneficial effect on the alpha(2C)-adrenoceptor affinity and potency. Replacing the piperazine ring proved difficult, with 1,4-diazepanes representing the only viable alternative.

  DOI：

  10.1021/jm060262x
• 作为产物：
  描述：

  2-乙基乙酰乙酸乙酯 在 对甲苯磺酸 作用下， 以 二苯醚 、 甲苯 为溶剂， 反应 1.0h， 生成 3-乙基-2-甲基喹啉-4-醇
  参考文献：
  名称：

  Structure−Activity Relationship of Quinoline Derivatives as Potent and Selective α_2C-Adrenoceptor Antagonists

  摘要：

  Starting from two acridine compounds identified in a high-throughput screening campaign (1 and 2, Table 1), a series of 4-aminoquinolines was synthesized and tested for their properties on the human alpha(2)-adrenoceptor subtypes (alpha(2A), alpha(2B), and alpha(2C.)). A number of compounds with good antagonist potencies against the alpha(2C)-adrenoceptor and excellent subtype selectivities over the other two subtypes were discovered. For example, (R)-{4-[4-(3,4-dimethylpiperazin-1-yl) phenylamino] quinolin- 3- yl} methanol 6j had an antagonist potency of 8.5 nM against, and a subtype selectivity of more than 200-fold for, the alpha(2C)-adrenoceptor. Investigation of the structure-activity relationship identified a number of structural features, the most critical of which was an absolute need for a substituent in the 3-position of the quinoline ring. The 3-position on the piperazine ring was also found to play an appreciable role, as substitutions in that position exerted a significant and stereospecific beneficial effect on the alpha(2C)-adrenoceptor affinity and potency. Replacing the piperazine ring proved difficult, with 1,4-diazepanes representing the only viable alternative.

  DOI：

  10.1021/jm060262x

文献信息

• [EN] ANTAGONISTS FOR ALPHA-2 ADRENOCEPTORS<br/>[FR] ANTAGONISTES POUR RECEPTEURS ALPHA-2 ADRENERGIQUES
  申请人：JUVANTIA PHARMA LTD OY

  公开号：WO2004067513A1

  公开（公告）日：2004-08-12

  The invention provides a compound of formula (I), wherein Q, Y, A, Ra, Rb, R1 to R4, u and t are as defined in claim 1, or a pharmaceutically acceptable salt or ester thereof, useful as an alpha-2 antagonist. The compounds of formula (I) can be used for the treatment of diseases or conditions where antagonists of alpha-2 adrenoceptors are indicated to be effective.

  该发明提供了一种具有式（I）的化合物，其中Q、Y、A、Ra、Rb、R1至R4、u和t如权利要求1中定义，或其药用可接受的盐或酯，可用作α-2拮抗剂。式（I）的化合物可用于治疗需要α-2肾上腺素受体拮抗剂有效的疾病或症状。
• Remarkably Efficient and Direct Route to Quinolines and Benzoazepines from the Condensation of Benzoxazinediones with Phosphonium Carbanion Salts
  作者：Wafaa M. Abdou、Azza A. Kamel

  DOI：10.1080/00397910701572670

  日期：2007.11

  Treatment of 2H-3,1-benzoxazine-2,4(1H)-dione (1a) with vinyltriphenyl-phosphonium bromide (2a) gives substituted benzoazepine 8a (48% yield) and indolizinone 12 (27% yield), whereas substituted quinolinone 15 and benzoazepine 8b were isolated from the reaction of N-methylisatoic anhydride (1b) and 2a. Furthermore, a series of quinoline derivatives was synthesized from the reactions of la and 1b with allyl-(2b), alkyl-(2c), (2d), and cyanomethyl-(3) triphenylphosphonium salts.
• Conrad; Limpach, Chemische Berichte, 1891, vol. 24, p. 2991
  作者：Conrad、Limpach

  DOI：——

  日期：——
• Gillis et al., Journal and Proceedings - Royal Society of New South Wales, 1939, vol. 73, p. 258,259,260
  作者：Gillis et al.

  DOI：——

  日期：——
• US6790239B1
  申请人：——

  公开号：US6790239B1

  公开（公告）日：2004-09-14