N-allyl-4-chloropicolinamide | 400082-49-7

• 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: N-allyl-4-chloropicolinamide
• 英文别名: (4-chloro(2-pyridyl))-N-allylcarboxamide；N-allyl-4-chloro-2-pyridinecarboxamide；4-chloro-N-prop-2-enylpyridine-2-carboxamide
• CAS: 400082-49-7
• 化学式: C₉H₉ClN₂O
• mdl: MFCD02185920
• 分子量: 196.636
• InChiKey: LAMKZJVCFAVBHN-UHFFFAOYSA-N

物化性质

• 沸点：
  342.3±37.0 °C(Predicted)
• 密度：
  1.205±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-二甲基碘苯 、 N-allyl-4-chloropicolinamide 在 silver(I) acetate 、 palladium diacetate 作用下， 以 甲苯 为溶剂， 反应 36.0h， 以76%的产率得到
  参考文献：
  名称：

  Pd(II)-Catalyzed, Picolinamide-Assisted, Z-Selective γ-Arylation of Allylamines To Construct Z-Cinnamylamines

  摘要：

  Investigations of Pd(II)-catalyzed, picolinamide-assisted, gamma-C(sp(2))-H activation and Z-selective arylation of allylamines are reported. The reactions of N-allylpicolinamides with various aryl iodides in the presence of the catalyst Pd(OAc)(2) and additive AgOAc have led to the selective gamma-arylation of allylamines to construct various cinnamylamines with moderate to good yields and good to high E/Z ratios. To obtain good E/Z ratios, the Pd(II)-catalyzed arylation reaction of N-allylpicolinamides was probed using different additives, directing groups, and reaction conditions. The Pd(II)-catalyzed arylation of an allylamine containing both gamma-C(sp(2))-(H) and gamma-C(sp(3)) H bonds afforded moderate yields of the gamma-C(sp(2)) H and gamma-C(sp3) H bisarylated cinnamylamines. Although Heck-type gamma-arylations of allylamines have generally afforded the E-cinnamylamines, the bidentate directing group picolinamide-directed arylations of allylamines were found to be Z-selective. A plausible mechanism was proposed for the observed regioselectivity and Z-selective arylation of N-allylpicolinamides. Additionally, the Pd(II)-catalyzed arylation of an N-allyl-5-methylisoxazole-3-carboxamide afforded the E-cinnarnylamines plausibly via a ligand-free Heck-type reaction mechanism.

  DOI：

  10.1021/acs.joc.7b00535
• 作为产物：
  描述：

  4-氯-2-吡啶甲酸 在 4-二甲氨基吡啶 、 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 N-allyl-4-chloropicolinamide
  参考文献：
  名称：

  Pd(II)-Catalyzed, Picolinamide-Assisted, Z-Selective γ-Arylation of Allylamines To Construct Z-Cinnamylamines

  摘要：

  Investigations of Pd(II)-catalyzed, picolinamide-assisted, gamma-C(sp(2))-H activation and Z-selective arylation of allylamines are reported. The reactions of N-allylpicolinamides with various aryl iodides in the presence of the catalyst Pd(OAc)(2) and additive AgOAc have led to the selective gamma-arylation of allylamines to construct various cinnamylamines with moderate to good yields and good to high E/Z ratios. To obtain good E/Z ratios, the Pd(II)-catalyzed arylation reaction of N-allylpicolinamides was probed using different additives, directing groups, and reaction conditions. The Pd(II)-catalyzed arylation of an allylamine containing both gamma-C(sp(2))-(H) and gamma-C(sp(3)) H bonds afforded moderate yields of the gamma-C(sp(2)) H and gamma-C(sp3) H bisarylated cinnamylamines. Although Heck-type gamma-arylations of allylamines have generally afforded the E-cinnamylamines, the bidentate directing group picolinamide-directed arylations of allylamines were found to be Z-selective. A plausible mechanism was proposed for the observed regioselectivity and Z-selective arylation of N-allylpicolinamides. Additionally, the Pd(II)-catalyzed arylation of an N-allyl-5-methylisoxazole-3-carboxamide afforded the E-cinnarnylamines plausibly via a ligand-free Heck-type reaction mechanism.

  DOI：

  10.1021/acs.joc.7b00535

文献信息

• Novel Microtubule-Interacting Phenoxy Pyridine and Phenyl Sulfanyl Pyridine Analogues for Cancer Therapy
  作者：Ravi Kumar Anchoori、Madeleine Susanne Quirine Kortenhorst、Manuel Hidalgo、Taradas Sarkar、Gurulingappa Hallur、Ruoli Bai、Paul J. Van Diest、Ernest Hamel、Saeed R. Khan

  DOI：10.1021/jm800203e

  日期：2008.10.9

  Current microtubule inhibitory agents used in the clinic to treat cancer have severe side effects, and development of resistance is frequent. We have evaluated the antitumor effect of a novel 30-compound library of phenoxy pyridine and phenyl sulfanyl pyridine derivatives. MTT assays revealed that, of all 30 compounds tested, compounds 2 and 3 showed the largest decrease in proliferation (low mu M range) against Panel and HS766T human pancreatic cancer cells. Flow cytometry experiments with MCF7 breast cancer cells showed a G2/M arrest comparable to that of colcemid. Immunofluorescence staining demonstrated complete disappearance of intracellular microtubules. Tubulin assembly assays, however, showed a dose-dependent decrease in tubulin assembly with compound 3 that seemed limited to about 50% of the control reaction. With compound 2 treatment, there was only a delay in the onset of assembly, with no effect on the extent of the reaction. Taken together, our results show that these novel microtubule inhibitors have promising anticancer activity and can be potentially used to overcome paclitaxel resistance in the clinical setting.
• Pd(II)-Catalyzed, Picolinamide-Assisted, <i>Z</i>-Selective γ-Arylation of Allylamines To Construct <i>Z</i>-Cinnamylamines
  作者：Ramarao Parella、Srinivasarao Arulananda Babu

  DOI：10.1021/acs.joc.7b00535

  日期：2017.7.7

  Investigations of Pd(II)-catalyzed, picolinamide-assisted, gamma-C(sp(2))-H activation and Z-selective arylation of allylamines are reported. The reactions of N-allylpicolinamides with various aryl iodides in the presence of the catalyst Pd(OAc)(2) and additive AgOAc have led to the selective gamma-arylation of allylamines to construct various cinnamylamines with moderate to good yields and good to high E/Z ratios. To obtain good E/Z ratios, the Pd(II)-catalyzed arylation reaction of N-allylpicolinamides was probed using different additives, directing groups, and reaction conditions. The Pd(II)-catalyzed arylation of an allylamine containing both gamma-C(sp(2))-(H) and gamma-C(sp(3)) H bonds afforded moderate yields of the gamma-C(sp(2)) H and gamma-C(sp3) H bisarylated cinnamylamines. Although Heck-type gamma-arylations of allylamines have generally afforded the E-cinnamylamines, the bidentate directing group picolinamide-directed arylations of allylamines were found to be Z-selective. A plausible mechanism was proposed for the observed regioselectivity and Z-selective arylation of N-allylpicolinamides. Additionally, the Pd(II)-catalyzed arylation of an N-allyl-5-methylisoxazole-3-carboxamide afforded the E-cinnarnylamines plausibly via a ligand-free Heck-type reaction mechanism.