6-cyanomethylpyridine-2-carboxylic acid ethyl ester | 178265-40-2

• 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: 6-cyanomethylpyridine-2-carboxylic acid ethyl ester
• 英文别名: Ethyl 6-(cyanomethyl)picolinate；ethyl 6-(cyanomethyl)pyridine-2-carboxylate
• CAS: 178265-40-2
• 化学式: C₁₀H₁₀N₂O₂
• mdl: MFCD09750012
• 分子量: 190.202
• InChiKey: ZBJVYPLOHORYBD-UHFFFAOYSA-N

物化性质

• 沸点：
  353.2±32.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  63
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  6-cyanomethylpyridine-2-carboxylic acid ethyl ester 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.5h， 生成
  参考文献：
  名称：

  Aerobic C–H Acetoxylation of 8-Methylquinoline in Pd^II–Pyridinecarboxylic Acid Systems: Some Structure–Reactivity Relationships

  摘要：

  Catalytic oxidative C-H acetoxylation of 8-methylquinoline as a model substrate with O-2 as oxidant was performed using palladium(II) carboxylate catalysts derived from four different pyridinecarboxylic acids able to form palladium(II) chelates of different size. A comparison of the rates of the substrate C-H activation and the O-2 activation steps shows that the C-H activation step is rate-limiting, whereas the O-2 activation occurs at a much faster rate already at 20 degrees C. The chelate ring size and the chelate ring strain of the catalytically active species are proposed to be the key factors affecting the rate of the C-H activation.

  DOI：

  10.1021/om400618n
• 作为产物：
  描述：

  乙基 6-甲基吡啶-2-羧酸酯 以 四氢呋喃 为溶剂， 反应 63.0h， 生成 6-cyanomethylpyridine-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Aerobic C–H Acetoxylation of 8-Methylquinoline in Pd^II–Pyridinecarboxylic Acid Systems: Some Structure–Reactivity Relationships

  摘要：

  Catalytic oxidative C-H acetoxylation of 8-methylquinoline as a model substrate with O-2 as oxidant was performed using palladium(II) carboxylate catalysts derived from four different pyridinecarboxylic acids able to form palladium(II) chelates of different size. A comparison of the rates of the substrate C-H activation and the O-2 activation steps shows that the C-H activation step is rate-limiting, whereas the O-2 activation occurs at a much faster rate already at 20 degrees C. The chelate ring size and the chelate ring strain of the catalytically active species are proposed to be the key factors affecting the rate of the C-H activation.

  DOI：

  10.1021/om400618n

文献信息

• An unusual anionic oxo–(µ-oxo)–vanadium(<scp>V</scp>) network interlinked by cationic sodium chains
  作者：Nathalie Julien-Cailhol、Eric Rose、Jaqueline Vaisserman、Dieter Rehder

  DOI：10.1039/dt9960002111

  日期：——

  The new compound 6-(1-cyano-2-hydroxyprop-1-enyl)pyridine-2-carboxylic acid (H(2)L) has been prepared and the structure of its ethyl ester determined. The salt NaHL reacted with VO2+ to form the vanadium(v) complex [Na(MeOH)(2)][VO(2)L]. Crystal-structure analysis of the complex revealed octahedral co-ordination of both the sodium and vanadium ions. Vanadium is co-ordinated to enolate oxygen, carboxylate oxygen, pyridine nitrogen, and two doubly bonded oxo groups in cis positions. The sixth position is occupied by the oxo group of a neighbouring vanadium centre at a rather long distance of 2.214(2) Angstrom. Anionic, asymmetrically ore-bridged vanadium chains are thus formed. These are interlinked by cationic sodium chains with sodium bonded to two bridging methanols, the cyano nitrogen of one of the vanadate chains and the co-ordinated carboxylate of the alternate vanadate chain. The network is further stabilized by hydrogen bonds. The relevance of the complex to biogenic vanadium compounds is discussed.
• Aerobic C–H Acetoxylation of 8-Methylquinoline in Pd^II–Pyridinecarboxylic Acid Systems: Some Structure–Reactivity Relationships
  作者：Daoyong Wang、Peter Y. Zavalij、Andrei N. Vedernikov

  DOI：10.1021/om400618n

  日期：2013.9.9

  Catalytic oxidative C-H acetoxylation of 8-methylquinoline as a model substrate with O-2 as oxidant was performed using palladium(II) carboxylate catalysts derived from four different pyridinecarboxylic acids able to form palladium(II) chelates of different size. A comparison of the rates of the substrate C-H activation and the O-2 activation steps shows that the C-H activation step is rate-limiting, whereas the O-2 activation occurs at a much faster rate already at 20 degrees C. The chelate ring size and the chelate ring strain of the catalytically active species are proposed to be the key factors affecting the rate of the C-H activation.