methyl 4-(pyridin-2-yl)hexanoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 4-(pyridin-2-yl)hexanoate
• 英文别名: Methyl 4-pyridin-2-ylhexanoate
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: BDAFZHNALXUGIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  Methyl 4-pyridin-2-ylpentanoate 、 三甲基环三硼氧烷 在 palladium diacetate copper diacetate 、 氧气 、 对苯醌 作用下， 以 溶剂黄146 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 以70%的产率得到methyl 4-(pyridin-2-yl)hexanoate
  参考文献：
  名称：

  Palladium-Catalyzed Alkylation of sp² and sp³ C−H Bonds with Methylboroxine and Alkylboronic Acids:  Two Distinct C−H Activation Pathways

  摘要：

  Palladium-catalyzed alkylations of sp2 and sp3 C-H bonds with either methylboroxine or alkylboronic acids were developed. Ag2O or AgCO3 is used as a crucial oxidant and promoter for the transmetalation step. Ether, ester, alcohol, and alkene functional groups are tolerated. A new C-H activation pathway differing from the cyclometalation process is elucidated using methylboroxine as the coupling partner.

  DOI：

  10.1021/ja0646747

文献信息

• [EN] TRANSITION METAL-CATALYZED ALKYLATION OF C-H BONDS WITH ORGANOBORON REAGENTS<br/>[FR] ALKYLATION À CATALYSEUR À BASE DE MÉTAL DE TRANSITION DE LIAISONS C-H AVEC DES RÉACTIFS D'ORGANOBORE
  申请人：BRANDEIS UNIVERSITY MS134

  公开号：WO2008024953A2

  公开（公告）日：2008-02-28

  [EN] One aspect of the present invention relates to methods for functionalization of 2-arylpyridine and arylpyrazoles with organoboron reagents in the presence of a transition metal catalyst to furnish alkylated arylpyridines and arylpyrazoles via regioselective functionalization of sp² -hybridized C-H bonds at a position ortho to the point of attachment of the pyridine or pyrazole ring to the aromatic nucleus, hi other embodiments, the present invention provides for alkylation of sp³-hybridized C-H bonds in alkylpyridines.
  [FR] Selon un mode de réalisation, la présente invention concerne des procédés de fonctionnalisation de 2-arylpyridine et d'arylpyrazoles avec des réactifs d'organobore en présence d'un catalyseur à base de métal de transition pour obtenir des arylpyridines et des arylpyrazoles par fonctionnalisation régiosélective de liaisons C-H à hybridation sp² en une position ortho au point de liaison du cycle pyridine ou pyrazole au noyau aromatique. Selon d'autres modes de réalisation, la présente invention concerne l'alkylation de liaisons C-H dans des alkylpyridines.
• Palladium-Catalyzed Alkylation of sp² and sp³ C−H Bonds with Methylboroxine and Alkylboronic Acids:  Two Distinct C−H Activation Pathways
  作者：Xiao Chen、Charles E. Goodhue、Jin-Quan Yu

  DOI：10.1021/ja0646747

  日期：2006.10.1

  Palladium-catalyzed alkylations of sp2 and sp3 C-H bonds with either methylboroxine or alkylboronic acids were developed. Ag2O or AgCO3 is used as a crucial oxidant and promoter for the transmetalation step. Ether, ester, alcohol, and alkene functional groups are tolerated. A new C-H activation pathway differing from the cyclometalation process is elucidated using methylboroxine as the coupling partner.