quinolin-5-yl pivalate | 1352192-11-0

• 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
• 英文名称: quinolin-5-yl pivalate
• 英文别名: Quinolin-5-yl 2,2-dimethylpropanoate；quinolin-5-yl 2,2-dimethylpropanoate
• CAS: 1352192-11-0
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: CONINVHTZFUICG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  quinolin-5-yl pivalate 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 lithium aluminium tetrahydride 、 三乙胺 、 间氯过氧苯甲酸 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 31.0h， 生成 2-(pyridine-3-ylethynyl)quinoline-5-ol
  参考文献：
  名称：

  Synthesis and biological evaluation of 2-(arylethynyl)quinoline derivatives as mGluR5 antagonists for the treatment of neuropathic pain

  摘要：

  We described here the synthesis and biological evaluation of mGluR5 antagonists containing a quinoline ring structure. Using intracellular calcium mobilization assay (FDSS assay), we identified compound 5n, showing high inhibitory activity against mGluR5. In addition, it was found that compound 5n has excellent stability profile. Finally, this compound exhibited favorable analgesic effects in spinal nerve ligation model of neuropathic pain, which is comparable to gabapentin. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.056
• 作为产物：
  描述：

  5-羟基喹啉 、 三甲基乙酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 以84%的产率得到quinolin-5-yl pivalate
  参考文献：
  名称：

  Synthesis and In vivo Evaluation of 5-Methoxy-2-(phenylethynyl)quinoline (MPEQ) and [¹¹C]MPEQ Targeting Metabotropic Glutamate Receptor 5 (mGluR5)

  摘要：

  本文描述了5-甲氧基-2-(苯乙炔)喹啉（MPEQ 3）作为潜在的mGluR5选择性放射配体的合成和体内评估。我们已确定MPEQ 3在神经病理性疼痛动物模型中表现出镇痛效果。通过FDG/PET成像评估了MPEQ 3存在下mGluR5对大鼠大脑神经活动的影响。此外，关于[$^{11}C$]MPEQ 3的PET研究证明，[$^{11}C$]MPEQ 3在大鼠大脑中的积累与mGluR5的定位相关。

  DOI：

  10.5012/bkcs.2014.35.8.2304

文献信息

• Nickel-Catalyzed α-Arylation of Ketones with Phenol Derivatives
  作者：Ryosuke Takise、Kei Muto、Junichiro Yamaguchi、Kenichiro Itami

  DOI：10.1002/anie.201403823

  日期：2014.6.23

  The nickel‐catalyzed α‐arylation of ketones with readily available phenol derivatives (esters and carbamates) provides access to useful α‐arylketones. For this transformation, 3,4‐bis(dicyclohexylphosphino)thiophene (dcypt) was identified as a new, enabling, air‐stable ligand for this transformation. The intermediate of an assumed CO oxidative addition was isolated and characterized by X‐ray crystal‐structure

  镍与容易获得的苯酚衍生物（酯和氨基甲酸酯）催化的α-芳基化反应提供了有用的α-芳基酮的获得途径。对于此转化，3,4-双（二环己基膦基）噻吩（dcypt）被确定为该转化的一种新的，稳定的，空气稳定的配体。假定C的中间 ö氧化加成物分离和表征通过X射线晶体结构分析。
• LIGAND, NICKEL COMPLEX COMPRISING THE LIGAND, AND REACTION USING THE NICKEL COMPLEX
  申请人：NATIONAL UNIVERSITY CORPORATION NAGOYA UNIVERSITY

  公开号：US20160074853A1

  公开（公告）日：2016-03-17

  An object of the present invention is to provide a method for directly performing arylation (particularly α-arylation) of carbonyl or thiocarbonyl compounds using a more inexpensive phenol derivative and nickel catalyst. Another object of the present invention is to provide a novel nickel catalyst that can be used in this method, and a novel ligand of the nickel catalyst. The novel compounds of the present invention are a compound having a diphosphine skeleton in which a five- or six-membered heterocyclic ring is substituted with two dialkylphosphines and/or dicycloalkylphosphines, or a salt thereof, and a compound having the diphosphine skeleton that is bound to nickel. Moreover, coupling reaction of a carbonyl compound and a phenol derivative can be advanced in the presence of a nickel compound having a monodentate or bidentate dialkylphosphine and/or dicycloalkylphosphine skeleton.

  本发明的一个目的是提供一种使用更便宜的酚衍生物和镍催化剂直接进行羟基化（尤其是α-羟基化）的醛或硫醛化合物的方法。本发明的另一个目的是提供一种可以用于该方法的新型镍催化剂，以及镍催化剂的新型配体。本发明的新化合物是一种含有二膦骨架的化合物，其中五元或六元杂环环被两个二烷基膦和/或二环烷基膦取代，或其盐，以及与镍结合的具有二膦骨架的化合物。此外，在存在具有一膦或二膦二烷基膦和/或二环烷基膦骨架的镍化合物的情况下，可以促进醛化合物和酚衍生物的偶联反应。
• Nickel-Catalyzed C–H/C–O Coupling of Azoles with Phenol Derivatives
  作者：Kei Muto、Junichiro Yamaguchi、Kenichiro Itami

  DOI：10.1021/ja210249h

  日期：2012.1.11

  The first nickel-catalyzed C-H bond arylation of azoles with phenol derivatives is described. The new Ni(cod)(2)/dcype catalytic system is active for the coupling of various phenol derivatives such as esters, carbamates, carbonates, sulfamates, triflates, tosylates, and mesylates. With this C-H/C-O biaryl coupling, we synthesized a series of privileged 2-arylazoles, including biologically active alkaloids. Moreover, we demonstrated the utility of the present reaction for functionalizing estrone and quinine.
• METHOD FOR PRODUCING PHENYL-SUBSTITUTED HETEROCYCLIC DERIVATIVE
  申请人：National University Corporation Nagoya University

  公开号：EP2774923B1

  公开（公告）日：2016-05-18
• US20140275549A1
  申请人：——

  公开号：US20140275549A1

  公开（公告）日：2014-09-18