methyl 6-phenylethynylnicotinate | 124300-48-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: methyl 6-phenylethynylnicotinate
• 英文别名: 6-Phenylethynyl-nicotinic acid methyl ester；methyl 6-(2-phenylethynyl)pyridine-3-carboxylate
• CAS: 124300-48-7
• 化学式: C₁₅H₁₁NO₂
• 分子量: 237.258
• InChiKey: DRFBUAIOGNADQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-氯烟酸甲酯 、 苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 三乙胺 作用下， 反应 8.0h， 以35%的产率得到methyl 6-phenylethynylnicotinate
  参考文献：
  名称：

  Positive and Negative Modulation of Group I Metabotropic Glutamate Receptors

  摘要：

  A discriminating pharmacophore model for noncompetitive metabotropic glutamate receptor antagonists of subtype 1 (mGluR1) was developed that facilitated the discovery of moderately active mGluR1 antagonists. One scaffold was selected for the design of several focused libraries where different substitution patterns were introduced. This approach facilitated the discovery of potent mGluR1 antagonists, as well as positive and negative mGluR5 modulators, because both receptor subtypes share similar binding pockets. For mGluR1 antagonists, a homology model of the mGlu1 receptor was established and a putative binding mode within the receptor's transmembrane domain was visualized.

  DOI：

  10.1021/jm0611298

文献信息

• A significant substituent effect on the regioselectivity in addition of alkynes to 3-substituted pyridines
  作者：Shinji Yamada、Aya Toshimitsu、Yasuko Takahashi

  DOI：10.1016/j.tet.2009.01.022

  日期：2009.3

  A substituent at the 3-position on a pyridine ring significantly affects the regioselectivity during the addition of alkynes to pyridinium salts. When the substituent is an electron-withdrawing group, 1,6-adducts are predominantly produced, whereas, 1,2-adducts become the major products when the substituent is an electron-donating group. The changes in the regioselectivity depending on the substituent

  吡啶环上3位的取代基会显着影响将炔烃加至吡啶鎓盐中的区域选择性。当取代基为吸电子基团时，主要产生1,6-加合物，而当取代基为给电子基团时，1,2-加合物成为主要产物。取决于取代基的区域选择性的变化可以通过产物稳定性的差异来解释。产生的二氢吡啶很容易与氯腈以定量产率芳香化为二取代的吡啶。
• Spin Frustrated Double Chain {[Fe(PZDA)H₂O)₂]·2H₂O}_n(H₂PZDA=2,3-Pyrazinedicarboxylic Acid)
  作者：Song Gao、Bao-Qing Ma、Tao Yi、Zhe-Ming Wang、Chun-Sheng Liao、Chun-Hua Yan、Guang-Xian Xu

  DOI：10.1246/cl.1999.773

  日期：1999.8

  A novel compound [Fe(PZDA)(H2O)2]·2H2O}n has been synthesized and its structure determined by X-ray diffraction analysis, which consists of a quasi-ladder-like double chain running along a axis where Fe(II) ions are linked through the carboxylic groups acting as the edges of the ladder and pyrazine rings functioning as the rungs. Variable-temperature magnetic susceptibility study indicates the presence of spin frustration in the double chain compound.

  合成了一种新化合物 [Fe(PZDA)(H2O)2]·2H2O}n，并通过 X 射线衍射分析确定了其结构。该化合物由沿 a 轴的准梯形双链构成，其中 Fe(II) 离子通过羧基相连，羧基作为梯子的边缘，而吡嗪环则作为梯子的横档。变温磁 susceptibili 研究表明，该双链化合物存在自旋挫折现象。
• NISHIWAKI, NAGATOSHI;MINAKATA, SATOSHI;KOMATSU, MITSUO;OHSHIRO, YOSHIKI, CHEM. LETT.,(1989) N, C. 773-776
  作者：NISHIWAKI, NAGATOSHI、MINAKATA, SATOSHI、KOMATSU, MITSUO、OHSHIRO, YOSHIKI

  DOI：——

  日期：——
• Positive and Negative Modulation of Group I Metabotropic Glutamate Receptors
  作者：Maksims Vanejevs、Claudia Jatzke、Steffen Renner、Sibylle Müller、Mirko Hechenberger、Tanja Bauer、Anna Klochkova、Ilya Pyatkin、Denis Kazyulkin、Elena Aksenova、Sergey Shulepin、Olga Timonina、Ariane Haasis、Aleksandrs Gutcaits、Christopher G. Parsons、Valerjans Kauss、Tanja Weil

  DOI：10.1021/jm0611298

  日期：2008.2.1

  A discriminating pharmacophore model for noncompetitive metabotropic glutamate receptor antagonists of subtype 1 (mGluR1) was developed that facilitated the discovery of moderately active mGluR1 antagonists. One scaffold was selected for the design of several focused libraries where different substitution patterns were introduced. This approach facilitated the discovery of potent mGluR1 antagonists, as well as positive and negative mGluR5 modulators, because both receptor subtypes share similar binding pockets. For mGluR1 antagonists, a homology model of the mGlu1 receptor was established and a putative binding mode within the receptor's transmembrane domain was visualized.