2-(m-tolyl)isonicotinonitrile | 158503-49-2

• 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: 2-(m-tolyl)isonicotinonitrile
• 英文别名: 2-(3-Methylphenyl)isonicotinonitrile；2-(3-methylphenyl)pyridine-4-carbonitrile
• CAS: 158503-49-2
• 化学式: C₁₃H₁₀N₂
• 分子量: 194.236
• InChiKey: DDRNSNAXFAZFHO-UHFFFAOYSA-N

物化性质

• 沸点：
  330.9±30.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  36.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(m-tolyl)isonicotinonitrile 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以92%的产率得到2-(间甲苯)异烟酸
  参考文献：
  名称：

  Synthesis and Biological Activities of New HMG-CoA Synthase Inhibitors: 2-Oxetanones with a Side Chain Containing Biphenyl, Terphenyl or Phenylpyridine

  摘要：

  A series of 1233A analogs containing biphenylyl, terphenylyl or phenylpyridyl groups in their side chain were synthesized and tested for the inhibitory activities against 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) synthase and inhibition for the cholesterol biosynthesis in the mouse liver. The compounds with an oxetane, cyclobutanone or gamma-butyrolactone ring as isosters of a 2-oxetanone ring were entirely inactive. Among sythetic analogs, anti-4-[3-[2-(5-isopropyl-2-pyridyl)-ethyl]-phenyl]ethyl]-3-hydroxymethyl-2-oxetanone (10b) was most active in vitro. The structure-activity relationships on the transformations of 2-oxetanone and its side chain were obtained.

  DOI：

  10.3987/com-94-6720
• 作为产物：
  描述：

  2-溴-4-氰基吡啶 、 3-甲基苯硼酸 在 四(三苯基膦)镍 、 sodium carbonate 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 2-(m-tolyl)isonicotinonitrile
  参考文献：
  名称：

  Synthesis and Biological Activities of New HMG-CoA Synthase Inhibitors: 2-Oxetanones with a Side Chain Containing Biphenyl, Terphenyl or Phenylpyridine

  摘要：

  A series of 1233A analogs containing biphenylyl, terphenylyl or phenylpyridyl groups in their side chain were synthesized and tested for the inhibitory activities against 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) synthase and inhibition for the cholesterol biosynthesis in the mouse liver. The compounds with an oxetane, cyclobutanone or gamma-butyrolactone ring as isosters of a 2-oxetanone ring were entirely inactive. Among sythetic analogs, anti-4-[3-[2-(5-isopropyl-2-pyridyl)-ethyl]-phenyl]ethyl]-3-hydroxymethyl-2-oxetanone (10b) was most active in vitro. The structure-activity relationships on the transformations of 2-oxetanone and its side chain were obtained.

  DOI：

  10.3987/com-94-6720

文献信息

• Iron-mediated direct arylation with arylboronic acids through an aryl radical transfer pathway
  作者：Jian Wang、Shan Wang、Gao Wang、Ji Zhang、Xiao-Qi Yu

  DOI：10.1039/c2cc35468c

  日期：——

  A novel iron-mediated direct C–H arylation of quinones and pyridine analogues with arylboronic acids has been developed using dichloromethane and water as solvents at ambient temperature. FeS is employed and serves as an efficient catalyst. A detailed reaction mechanism is speculated and expounded.

  一种新型铁介导的醌和吡啶类似物与芳基硼酸直接C-H芳基化反应已开发出来，使用二氯甲烷和水作为溶剂，在常温下进行。FeS被用作高效的催化剂，详细推测并阐述了反应机理。
• Direct Arylation of Substituted Pyridines with Arylboronic Acids Catalyzed by Iron(II) Oxalate
  作者：Yibo Huang、Dan Guan、Liang Wang

  DOI：10.1002/cjoc.201400528

  日期：2014.12

  The direct arylation of substituted pyridines with several arylboronic acids has been developed. This transformation could proceed readily at ambient temperature using inexpensive reagents: iron(II) oxalate as a catalyst, potassium persulfate as a co‐oxidant, which can afford the arylated products in mild to good yields. The mechanism is presumed to proceed through a nucleophilic radical addition to

  已经开发了取代的吡啶与几种芳基硼酸的直接芳基化。使用廉价的试剂：草酸亚铁（II）作为催化剂，过硫酸钾作为助氧化剂，可以在环境温度下轻松进行这种转化，从而可以提供中等收率到良好收率的芳基化产物。推测该机理是通过原位再氧化将亲核基团加到吡啶上进行的。
• Synthesis and Biological Activities of New HMG-CoA Synthase Inhibitors: 2-Oxetanones with a Side Chain Containing Biphenyl, Terphenyl or Phenylpyridine
  作者：Hirokazu Hashizume、Hajime Ito、Naoaki Kanaya、Hajime Nagashima、Hiroyuki Usui、Reiko Oshima、Munefumi Kanao、Hiroshi Tomoda、Toshiaki Sunazuka、Tohru Nagamitsu、Hidetoshi Kumagai、Satoshi Omura

  DOI：10.3987/com-94-6720

  日期：——

  A series of 1233A analogs containing biphenylyl, terphenylyl or phenylpyridyl groups in their side chain were synthesized and tested for the inhibitory activities against 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) synthase and inhibition for the cholesterol biosynthesis in the mouse liver. The compounds with an oxetane, cyclobutanone or gamma-butyrolactone ring as isosters of a 2-oxetanone ring were entirely inactive. Among sythetic analogs, anti-4-[3-[2-(5-isopropyl-2-pyridyl)-ethyl]-phenyl]ethyl]-3-hydroxymethyl-2-oxetanone (10b) was most active in vitro. The structure-activity relationships on the transformations of 2-oxetanone and its side chain were obtained.