(E)-3-(tetrahydro-2H-pyran-4-yl)acrylic acid | 1278963-15-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (E)-3-(tetrahydro-2H-pyran-4-yl)acrylic acid
• 英文别名: 3-(oxan-4-yl)prop-2-enoic acid
• CAS: 1278963-15-7
• 化学式: C₈H₁₂O₃
• mdl: MFCD18785166
• 分子量: 156.181
• InChiKey: DPGYZWXDYCAFNI-UHFFFAOYSA-N

物化性质

• 沸点：
  330.1±17.0 °C(Predicted)
• 密度：
  1.220±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.625
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(tetrahydro-2H-pyran-4-yl)acrylic acid 在 草酰氯 、 铁粉 、 sodium hydride 、 溶剂黄146 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 为溶剂， 生成 2-[2-(oxan-4-yl)ethenyl]-6-[2-(trifluoromethyl)phenyl]-1H-benzimidazole
  参考文献：
  名称：

  Discovery of vinylcycloalkyl-substituted benzimidazole TRPM8 antagonists effective in the treatment of cold allodynia

  摘要：

  Thermosensitive transient receptor potential melastatin 8 (TRPM8) antagonists are considered to be potential therapeutic agents for the treatment of cold hypersensitivity. The discovery of a new class of TRPM8 antagonists that shows in vivo efficacy in the rat chronic constriction injury (CCI)-induced model of neuropathic pain is described. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.060
• 作为产物：
  描述：

  tetrahydro-4-(methoxymethylene)-2H-pyran 在 哌啶 作用下， 以 吡啶 为溶剂， 生成 (E)-3-(tetrahydro-2H-pyran-4-yl)acrylic acid
  参考文献：
  名称：

  Discovery of vinylcycloalkyl-substituted benzimidazole TRPM8 antagonists effective in the treatment of cold allodynia

  摘要：

  Thermosensitive transient receptor potential melastatin 8 (TRPM8) antagonists are considered to be potential therapeutic agents for the treatment of cold hypersensitivity. The discovery of a new class of TRPM8 antagonists that shows in vivo efficacy in the rat chronic constriction injury (CCI)-induced model of neuropathic pain is described. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.060

文献信息

• Synthesis and antibacterial activities of some novel 17, 18-unsaturated carbonyl compounds derivated from josamycin
  作者：Zhe-Hui Zhao、Long-Long Jin、Yan-Peng Xu、Chao Liu、A-Peng Wang、Ping-Sheng Lei

  DOI：10.1080/10286020.2016.1194834

  日期：2017.4.3

  Some novel josamycin derivatives bearing an arylalkyl-type side chain were designed and synthesized. By HWE or Wittig reaction, 16-aldehyde group of josamycin analogs were converted into unsaturated carbonyl compounds. They were evaluated for their in vitro antibacterial activities against a panel of respiratory pathogens. 8b and 8e exhibited comparable activities against a panel of respiratory pathogens

  设计并合成了一些带有芳烷基型侧链的新型久沙霉素衍生物。通过HWE或Wittig反应，将交沙霉素类似物的16-醛基转化为不饱和羰基化合物。评估了他们对一组呼吸道病原体的体外抗菌活性。图8b和图8e显示了针对一组呼吸道病原体的相当的活性，特别是对于一系列去霉菌糖基久他霉素类似物中的抗性病原体。在所有目标分子中，有21种显示出最佳的抗菌活性。
• Discovery of 4-[4-({(3R)-1-butyl-3-[(R)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undec-9-yl}methyl)phenoxy]benzoic acid hydrochloride: A highly potent orally available CCR5 selective antagonist
  作者：Rena Nishizawa、Toshihiko Nishiyama、Katsuya Hisaichi、Chiaki Minamoto、Masayuki Murota、Yoshikazu Takaoka、Hisao Nakai、Hideaki Tada、Kenji Sagawa、Shiro Shibayama、Daikichi Fukushima、Kenji Maeda、Hiroaki Mitsuya

  DOI：10.1016/j.bmc.2011.05.022

  日期：2011.7

  Based on the original spirodiketopiperazine design framework, further optimization of an orally available CCR5 antagonist was undertaken. Structural hybridization of the hydroxylated analog 4 derived from one of the oxidative metabolites and the new orally available non-hydroxylated benzoic acid analog 5 resulted in another potent orally available CCR5 antagonist 6a as a clinical candidate. Full details of a structure-activity relationship (SAR) study and ADME properties are presented. (C) 2011 Elsevier Ltd. All rights reserved.