(6-氯吡啶-3-基)-邻甲苯-甲酮 | 872088-10-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (6-氯吡啶-3-基)-邻甲苯-甲酮
• 英文名称: 2-methylphenyl-2-chloropyrid-5-ylketone
• 英文别名: 2-Chloro-5-(2-methylbenzoyl)pyridine；(6-chloropyridin-3-yl)-(2-methylphenyl)methanone
• CAS: 872088-10-3
• 化学式: C₁₃H₁₀ClNO
• 分子量: 231.681
• InChiKey: PCMVURXUYXTDRG-UHFFFAOYSA-N

物化性质

• 沸点：
  347.4±32.0 °C(Predicted)
• 密度：
  1.225±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (6-氯吡啶-3-基)-邻甲苯-甲酮 在 sodium tetrahydroborate 、 1-氯乙基氯甲酸酯 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 42.7h， 生成 3-(2-methylphenyl-2-chloropyrid-5-ylmethoxy)azetidine
  参考文献：
  名称：

  Fatty acid amide hydrolase inhibitors. 3: Tetra-substituted azetidine ureas with in vivo activity

  摘要：

  We describe here our attempts to optimise the human fatty acid amide hydrolase (FAAH) inhibition and physicochemical properties of our previously reported tetrasubstituted azetidine urea FAAH inhibitor, VER-156084. We describe the SAR of a series of analogues and conclude with the demonstration of in vivo dose-dependant FAAH inhibition in an anandamide-loading study in rats. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.032
• 作为产物：
  描述：

  6-氯吡啶-3-羰酰氯 在 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 19.25h， 生成 (6-氯吡啶-3-基)-邻甲苯-甲酮
  参考文献：
  名称：

  Fatty acid amide hydrolase inhibitors. 3: Tetra-substituted azetidine ureas with in vivo activity

  摘要：

  We describe here our attempts to optimise the human fatty acid amide hydrolase (FAAH) inhibition and physicochemical properties of our previously reported tetrasubstituted azetidine urea FAAH inhibitor, VER-156084. We describe the SAR of a series of analogues and conclude with the demonstration of in vivo dose-dependant FAAH inhibition in an anandamide-loading study in rats. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.032

文献信息

• Addition of Grignard Reagents to Aryl Acid Chlorides:  An Efficient Synthesis of Aryl Ketones
  作者：Xiao-jun Wang、Li Zhang、Xiufeng Sun、Yibo Xu、Dhileepkumar Krishnamurthy、Chris H. Senanayake

  DOI：10.1021/ol052150q

  日期：2005.12.1

  addition of Grignard reagents to acid chlorides in the presence of bis[2-(N,N-dimethylamino)ethyl] ether proceeds selectively to provide aryl ketones in high yields. A possible tridentate interaction between Grignard reagents and bis[2-(N,N-dimethylamino)ethyl] ether moderates the reactivity of Grignard reagents, preventing the newly formed ketones from nucleophilic addition by Grignard reagents.

  [化学反应：见正文]。在双[2-（N，N-二甲基氨基）乙基]醚存在下，将格氏试剂直接添加到酰氯中选择性地进行，以高收率提供芳基酮。格氏试剂与双[2-（N，N-二甲基氨基）乙基]醚之间可能的三齿相互作用会减缓格氏试剂的反应性，从而防止新形成的酮被格氏试剂亲核加成。
• Aminoimidazo[1,2-a]pyridines as a new structural class of cyclin-dependent kinase inhibitors. Part 1: Design, synthesis, and biological evaluation
  作者：Carlos Jaramillo、J. Eugenio de Diego、Chafiq Hamdouchi、Elizabeth Collins、Heather Keyser、Concha Sánchez-Martı́nez、Miriam del Prado、Bryan Norman、Harold B. Brooks、Scott A. Watkins、Charles D. Spencer、Jack Alan Dempsey、Bryan D. Anderson、Robert M. Campbell、Tellie Leggett、Bharvin Patel、Richard M. Schultz、Juan Espinosa、Michal Vieth、Faming Zhang、David E. Timm

  DOI：10.1016/j.bmcl.2004.09.053

  日期：2004.12

  We have identified a novel structural class of protein serine/threonine kinase inhibitors comprised of an aminoimidazo[1,2-a]pyridine nucleus. Compounds from this family are shown to potently inhibit cyclin-dependent kinases by competing with ATP for binding to a catalytic subunit of the protein. Structure-based design approach was used to direct this chemical scaffold toward generating potent and

  我们已经确定了由氨基咪唑并[1,2-a]吡啶核组成的蛋白质丝氨酸/苏氨酸激酶抑制剂的新型结构类别。已显示该家族化合物通过与ATP竞争结合蛋白的催化亚基而有效抑制细胞周期蛋白依赖性激酶。基于结构的设计方法用于指导该化学支架产生有效的和选择性的CDK2抑制剂。这类新型的ATP定位的蛋白激酶抑制剂氨基咪唑并[1,2-a]吡啶类化合物的发现，为寻求有效治疗癌症和其他涉及蛋白激酶信号传导途径的疾病的药物化学工具提供了基础。
• Fatty acid amide hydrolase inhibitors. 3: Tetra-substituted azetidine ureas with in vivo activity
  作者：Stephen D. Roughley、Helen Browne、Alba T. Macias、Karen Benwell、Teresa Brooks、Jalanie D’Alessandro、Zoe Daniels、Sarah Dugdale、Geraint Francis、Ben Gibbons、Terance Hart、Timothy Haymes、Guy Kennett、Sean Lightowler、Natalia Matassova、Howard Mansell、Angela Merrett、Anil Misra、Anthony Padfield、Rachel Parsons、Robert Pratt、Alan Robertson、Heather Simmonite、Kiri Tan、Steven B. Walls、Melanie Wong

  DOI：10.1016/j.bmcl.2011.12.032

  日期：2012.1

  We describe here our attempts to optimise the human fatty acid amide hydrolase (FAAH) inhibition and physicochemical properties of our previously reported tetrasubstituted azetidine urea FAAH inhibitor, VER-156084. We describe the SAR of a series of analogues and conclude with the demonstration of in vivo dose-dependant FAAH inhibition in an anandamide-loading study in rats. (C) 2011 Elsevier Ltd. All rights reserved.