butyl(2-thienylmethyl)ether | 90611-42-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: butyl(2-thienylmethyl)ether
• 英文别名: 2-(Butoxymethyl)thiophene
• CAS: 90611-42-0
• 化学式: C₉H₁₄OS
• 分子量: 170.276
• InChiKey: OXGFYOOUMPYSNV-UHFFFAOYSA-N

物化性质

• 沸点：
  214.9±15.0 °C(Predicted)
• 密度：
  1.015±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  37.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  butyl(2-thienylmethyl)ether 在 正丁基锂 、 potassium tert-butylate 、 氧气 、 2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.67h， 生成 3-(5-(2-butoxymethyl)thiophen-2-yl)-2-(pyrimidin-2-yl)-1,2,3,4-tetrahydro-9H-pyrrolo[3,4-b]quinolin-9-one
  参考文献：
  名称：

  Design and synthesis of furyl/thineyl pyrroloquinolones based on natural alkaloid perlolyrine, lead to the discovery of potent and selective PDE5 inhibitors

  摘要：

  Based on perlolyrine (1), a natural alkaloid with weak PDE5 potency from the traditional Chinese aphrodisiac plant Tribulus terrestris L., a series alpha-substituted tetrahydro-beta-carboline (TH beta C) derivatives were synthesized via T(+)BF4(-)-mediated oxidative C-H functionalization of N-aryl TH beta Cs with diverse potassium trifluoroborates. Following Winterfeldt oxidation afforded the corresponding furyl/thienyl pyrroloquinolones, of which 5-ethylthiophene/ethylfuran derivatives 20a-b were identified as the most potent and selective PDE5 inhibitors. Among the enantiomers, (S)-20a and (S)-20b (IC50 = 0.52 and 0.39 nM) were found to be more effective than their (R)-antipode, display favorable pharmacokinetic profiles, exert in vitro vasorelaxant effects on the isolated thoracic aorta, and exhibit in vivo efficacy in the anesthetized rabbit erectile model. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.02.039
• 作为产物：
  描述：

  2-(二丁氧基甲基)噻吩 在 三氟化硼乙醚 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.25h， 以53%的产率得到butyl(2-thienylmethyl)ether
  参考文献：
  名称：

  Raja, S.; Xavier, N.; Arulraj, S. J., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1989, vol. 28, # 1-11, p. 687 - 689

  摘要：

  DOI：

文献信息

• Raja, S.; Xavier, N.; Arulraj, S. J., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 916 - 919
  作者：Raja, S.、Xavier, N.、Arulraj, S. J.

  DOI：——

  日期：——
• RAJA, S.;XAVIER, N.;ARULRAJ, S. J., INDIAN J. CHEM. B, 28,(1989) N, C. 687-689
  作者：RAJA, S.、XAVIER, N.、ARULRAJ, S. J.

  DOI：——

  日期：——
• Design and synthesis of furyl/thineyl pyrroloquinolones based on natural alkaloid perlolyrine, lead to the discovery of potent and selective PDE5 inhibitors
  作者：Hongbo Zheng、Lin Li、Bin Sun、Yun Gao、Wei Song、Xiaoyu Zhao、Yanhui Gao、Zhiyu Xie、Nianzhao Zhang、Jianbo Ji、Huiqing Yuan、Hongxiang Lou

  DOI：10.1016/j.ejmech.2018.02.039

  日期：2018.4

  Based on perlolyrine (1), a natural alkaloid with weak PDE5 potency from the traditional Chinese aphrodisiac plant Tribulus terrestris L., a series alpha-substituted tetrahydro-beta-carboline (TH beta C) derivatives were synthesized via T(+)BF4(-)-mediated oxidative C-H functionalization of N-aryl TH beta Cs with diverse potassium trifluoroborates. Following Winterfeldt oxidation afforded the corresponding furyl/thienyl pyrroloquinolones, of which 5-ethylthiophene/ethylfuran derivatives 20a-b were identified as the most potent and selective PDE5 inhibitors. Among the enantiomers, (S)-20a and (S)-20b (IC50 = 0.52 and 0.39 nM) were found to be more effective than their (R)-antipode, display favorable pharmacokinetic profiles, exert in vitro vasorelaxant effects on the isolated thoracic aorta, and exhibit in vivo efficacy in the anesthetized rabbit erectile model. (C) 2018 Elsevier Masson SAS. All rights reserved.
• Raja, S.; Xavier, N.; Arulraj, S. J., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1989, vol. 28, # 1-11, p. 687 - 689
  作者：Raja, S.、Xavier, N.、Arulraj, S. J.

  DOI：——

  日期：——