N-phenyloxycarbonyl 3-cyanopyridinium chloride

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-phenyloxycarbonyl 3-cyanopyridinium chloride
• 英文别名: Phenyl 3-cyanopyridin-1-ium-1-carboxylate;chloride
• 化学式: C₁₃H₉N₂O₂*Cl
• 分子量: 260.68
• InChiKey: FYHOWCLJUOKIAS-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  对溴丁氧基苯 、 N-phenyloxycarbonyl 3-cyanopyridinium chloride 在 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以95%的产率得到phenyl 2-(4-butoxyphenyl)-5-cyano-2H-pyridine-1-carboxylate
  参考文献：
  名称：

  FACILE SYNTHESIS OF A SERIES OF LIQUID CRYSTALLINE 2-(4'-ALKOXYPHENYL)-5-CYANOPYRIDINES

  摘要：

  该发明涉及一种简便合成一系列2-(4′-烷氧基苯基)-5-氰基吡啶液晶化合物的方法，该化合物由以下式(I)表示：其中CnH2n+1是具有2-12个碳原子的直链烷基基团。该液晶化合物2-(4′-烷氧基苯基)-5-氰基吡啶的合成完成于两步反应中。首先，将格氏试剂（如4-烷氧基苯基溴化镁）加入到3-氰基吡啶盐（如N-苯氧羰基-3-氰基吡啶盐酸盐）中，得到1,2-二氢吡啶。然后，将1,2-二氢吡啶与邻氯苯醌氧化，得到2-(4′-烷氧基苯基)-5-氰基吡啶。

  公开号：

  US20080306276A1
• 作为产物：
  描述：

  3-氰基吡啶 、 氯甲酸苯酯 以 乙腈 为溶剂， 生成 N-phenyloxycarbonyl 3-cyanopyridinium chloride
  参考文献：
  名称：

  Kinetics and Mechanism of the Pyridinolysis of Phenyl Chloroformates in Acetonitrile

  摘要：

  Kinetic studies on the reactions of Y-phenyl chloroformates with X-pyridines in acetonitrile are carried out at 25.0 degrees C. Both the Hammett and Bronsted plots are linear with enhanced substituent constants, sigma(p)(-), and basicities, pK(a)(-), for strong para pi-acceptor X-substituents, p-CN and p-CH3CO. This indicates that the electron-rich formate (O-C-O) moiety overlaps with the pyridine ring pi-system enabling, through conjugation with the para pi-acceptors, the rate-limiting formation of a tetrahedral intermediate. The difference in the aminolysis mechanism between methyl, II, and phenyl chloroformate, III, is attributed to the much stronger electron-donating polarizability effect of C6H5, than of CH3. The proposed mechanism is supported by a relatively small beta(X) (congruent to 0.3) and by the lower Delta H double dagger (6.7 kcal mol(-1)) and Delta S double dagger (-44 eu) values for a stronger donor Y (Y = p-CH3O) coupled with a stronger para pi-acceptor (X = p-CN) in pyridine.

  DOI：

  10.1021/jo9814905

文献信息

• FACILE SYNTHESIS OF A SERIES OF LIQUID CRYSTALLINE 2-(4'-ALKOXYPHENYL)-5-CYANOPYRIDINES
  申请人：Chia Win-Long

  公开号：US20080306276A1

  公开（公告）日：2008-12-11

  The invention relates to a facile synthesis of a series of 2-(4′-alkoxyphenyl)-5-cyanopyridine liquid crystal compounds which are represented by the following formula (I): wherein C n H 2n+1 is a linear alkyl group having 2-12 carbon atoms. The synthesis of the liquid crystalline 2-(4′-alkoxyphenyl)-5-cyanopyridine is completed in a two-step reaction. First, a Grignard reagent (such as 4-alkoxyphenylmagnesium bromide) is added to a 3-cyanopyridinium salt (such as N-phenyloxycarbonyl-3-cyanopyridinium chloride) to get a 1,2-dihydropyridine. Then, the 1,2-dihydropyridine is oxidized with o-chloronil to obtain the 2-(4′-alkoxyphenyl)-5-cyanopyridine.

  该发明涉及一种简便合成一系列2-(4′-烷氧基苯基)-5-氰基吡啶液晶化合物的方法，该化合物由以下式(I)表示：其中CnH2n+1是具有2-12个碳原子的直链烷基基团。该液晶化合物2-(4′-烷氧基苯基)-5-氰基吡啶的合成完成于两步反应中。首先，将格氏试剂（如4-烷氧基苯基溴化镁）加入到3-氰基吡啶盐（如N-苯氧羰基-3-氰基吡啶盐酸盐）中，得到1,2-二氢吡啶。然后，将1,2-二氢吡啶与邻氯苯醌氧化，得到2-(4′-烷氧基苯基)-5-氰基吡啶。
• Facile synthesis of a series of liquid crystalline 2-(4'-alkylphenyl)-5-cyanopyridines
  申请人：Chia Win-Long

  公开号：US20080146813A1

  公开（公告）日：2008-06-19

  The invention relates to a facile synthesis of a series of 2-(4′-alkylphenyl)-5-cyanopyridine liquid crystal compounds which are represented by the following formula (I): wherein C n is a linear alkyl having 1-12 carbon atoms. The synthesis of the liquid crystalline 2-(4′-alkylphenyl)-5-cyanopyridine is completed in a two-step reaction. First, a Grignard reagent (such as 4-alkylphenylmagnesium bromide) is added to a 3-cyanopyridinium salt (such as N-phenyloxycarbonyl-3-cyanopyridinium chloride) to get a 1,2-dihydropyridine. Then the 1,2-dihydropyridine is oxidized with o-chloronil to obtain the 2-(4′-alkylphenyl)-5-cyanopyridine.

  本发明涉及一种简便的合成一系列2-(4'-烷基苯基)-5-氰基吡啶液晶化合物的方法，其化学式如下（I）：其中，Cn为具有1-12个碳原子的线性烷基。制备液晶2-(4'-烷基苯基)-5-氰基吡啶的方法包括两个步骤的反应。首先，将格氏试剂（例如4-烷基苯基镁溴化物）加入到3-氰基吡啶盐（例如N-苯氧羰基-3-氰基吡啶盐酸盐）中，得到1,2-二氢吡啶。然后，使用邻氯硝基苯氧化剂氧化1,2-二氢吡啶，得到2-(4'-烷基苯基)-5-氰基吡啶。
• Kinetics and Mechanism of the Pyridinolysis of Phenyl Chloroformates in Acetonitrile
  作者：Han Joong Koh、Kwang Lae Han、Hai Whang Lee、Ikchoon Lee

  DOI：10.1021/jo9814905

  日期：1998.12.1

  Kinetic studies on the reactions of Y-phenyl chloroformates with X-pyridines in acetonitrile are carried out at 25.0 degrees C. Both the Hammett and Bronsted plots are linear with enhanced substituent constants, sigma(p)(-), and basicities, pK(a)(-), for strong para pi-acceptor X-substituents, p-CN and p-CH3CO. This indicates that the electron-rich formate (O-C-O) moiety overlaps with the pyridine ring pi-system enabling, through conjugation with the para pi-acceptors, the rate-limiting formation of a tetrahedral intermediate. The difference in the aminolysis mechanism between methyl, II, and phenyl chloroformate, III, is attributed to the much stronger electron-donating polarizability effect of C6H5, than of CH3. The proposed mechanism is supported by a relatively small beta(X) (congruent to 0.3) and by the lower Delta H double dagger (6.7 kcal mol(-1)) and Delta S double dagger (-44 eu) values for a stronger donor Y (Y = p-CH3O) coupled with a stronger para pi-acceptor (X = p-CN) in pyridine.
• US7465802B2
  申请人：——

  公开号：US7465802B2

  公开（公告）日：2008-12-16
• US7872143B2
  申请人：——

  公开号：US7872143B2

  公开（公告）日：2011-01-18