N-(2-甲氧基-4-甲基苯基)-3-苯基丙烯酰胺 | 349146-21-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 中文名称: N-(2-甲氧基-4-甲基苯基)-3-苯基丙烯酰胺
• 英文名称: N-(2-methoxy-4-methylphenyl)-3-phenylprop-2-enamide
• CAS: 349146-21-0
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: VGFOMRNGOACZHH-UHFFFAOYSA-N

物化性质

• 沸点：
  476.4±45.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-甲氧基-4-甲基苯基)-3-苯基丙烯酰胺 在 盐酸 、 aluminum (III) chloride 、 bis(triphenylylphosphine)palladium(II) dichloride 、 氢溴酸 、 二甲基二环氧乙烷 、 potassium carbonate 作用下， 以 四氢呋喃 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 氯苯 、 异丙醇 、 丙酮 为溶剂， 反应 80.0h， 生成 5-[2-(5,6-diethyl-indan-2-ylamino)-1-hydroxy-ethyl]-8-hydroxy-6-methyl-1H-quinolin-2-one
  参考文献：
  名称：

  An investigation into the structure–activity relationships associated with the systematic modification of the β2-adrenoceptor agonist indacaterol

  摘要：

  The synthesis of a series of indacaterol analogues in which each of the three structural regions of indacaterol are modified in a systematic manner is described. Evaluation of the affinity of these analogues for the beta(2)-adrenoceptor identified the 3,4-dihydroquinolinone and 5-n-butylindanyl analogues to demonstrate the most similar profiles to indacaterol. An alpha-methyl aminoindane analogue was discovered to be 25-fold more potent than indacaterol, and functional studies revealed an atypical beta(2)-adrenoceptor activation profile for this compound consistent with that of a slowly dissociating 'super agonist'. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.096
• 作为产物：
  描述：

  2-甲氧基-4-甲基苯胺 、 肉桂酰氯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以92%的产率得到N-(2-甲氧基-4-甲基苯基)-3-苯基丙烯酰胺
  参考文献：
  名称：

  An investigation into the structure–activity relationships associated with the systematic modification of the β2-adrenoceptor agonist indacaterol

  摘要：

  The synthesis of a series of indacaterol analogues in which each of the three structural regions of indacaterol are modified in a systematic manner is described. Evaluation of the affinity of these analogues for the beta(2)-adrenoceptor identified the 3,4-dihydroquinolinone and 5-n-butylindanyl analogues to demonstrate the most similar profiles to indacaterol. An alpha-methyl aminoindane analogue was discovered to be 25-fold more potent than indacaterol, and functional studies revealed an atypical beta(2)-adrenoceptor activation profile for this compound consistent with that of a slowly dissociating 'super agonist'. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.096

文献信息

• An investigation into the structure–activity relationships associated with the systematic modification of the β2-adrenoceptor agonist indacaterol
  作者：David Beattie、David Beer、Michelle E. Bradley、Ian Bruce、Steven J. Charlton、Bernard M. Cuenoud、Robin A. Fairhurst、David Farr、John R. Fozard、Diana Janus、Elizabeth M. Rosethorne、David A. Sandham、David A. Sykes、Alexandre Trifilieff、Katharine L. Turner、Elke Wissler

  DOI：10.1016/j.bmcl.2012.07.096

  日期：2012.10

  The synthesis of a series of indacaterol analogues in which each of the three structural regions of indacaterol are modified in a systematic manner is described. Evaluation of the affinity of these analogues for the beta(2)-adrenoceptor identified the 3,4-dihydroquinolinone and 5-n-butylindanyl analogues to demonstrate the most similar profiles to indacaterol. An alpha-methyl aminoindane analogue was discovered to be 25-fold more potent than indacaterol, and functional studies revealed an atypical beta(2)-adrenoceptor activation profile for this compound consistent with that of a slowly dissociating 'super agonist'. (C) 2012 Elsevier Ltd. All rights reserved.