4,7-dichloro-1-methylquinolinium triflate | 1255923-14-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4,7-dichloro-1-methylquinolinium triflate
• 英文别名: 4,7-dichloro-N-methylquinolinium triflate；4,7-Dichloro-1-methylquinolin-1-ium;trifluoromethanesulfonate；4,7-dichloro-1-methylquinolin-1-ium;trifluoromethanesulfonate
• CAS: 1255923-14-8
• 化学式: CF₃O₃S*C₁₀H₈Cl₂N
• 分子量: 362.157
• InChiKey: YYQRVPVIXQKDPZ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  69.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  四(三苯基膦)钯 、 4,7-dichloro-1-methylquinolinium triflate 以 甲苯 为溶剂， 以62.9%的产率得到trans-chloro(7-chloro-4-hydro-1-methyl-4-quinolylidene)bis(triphenylphosphine)palladium(II) triflate
  参考文献：
  名称：

  Pyridine-Derived N-Heterocyclic Carbenes: An Experimental and Theoretical Evaluation of the Bonding in and Reactivity of Selected Normal and Abnormal Complexes of Nickel(II) and Palladium(II)

  摘要：

  We report a thorough investigation of a series of isomeric complexes with the general formula trans-(pyridylidene)M(PPh3)(2)Cl (M = Pd, Ni). For the first time, a systematic comparison of normal, abnormal, and remote bonding modes is presented. X-ray structural and C-13 NMR data indicate the importance of carbenoid mesomeric contributions in their compound class.. The catalytic performance of the palladium complexes trans-(pyridylidene)Pd(PPh3)(2)Cl as precursors in Suzuki-Miyaura-type cross-coupling suggests a correlation of remote bonding with catalyst robustness and effectivity. When metal precursors M(PPh3)(4) are reacted with 2,4-dichloropyridinium salts, preferential formation of remote carbene complexes occurs and indications are that electronic parameters rather than steric influences are responsible for the observed selectivity. Calculations at the BP86/TZ2P level of theory support interpretation of the results.

  DOI：

  10.1021/om100431u
• 作为产物：
  描述：

  4,7-二氯喹啉 、 三氟甲烷磺酸甲酯 以 二氯甲烷 为溶剂， 反应 18.0h， 以99%的产率得到4,7-dichloro-1-methylquinolinium triflate
  参考文献：
  名称：

  Pyridine-Derived N-Heterocyclic Carbenes: An Experimental and Theoretical Evaluation of the Bonding in and Reactivity of Selected Normal and Abnormal Complexes of Nickel(II) and Palladium(II)

  摘要：

  We report a thorough investigation of a series of isomeric complexes with the general formula trans-(pyridylidene)M(PPh3)(2)Cl (M = Pd, Ni). For the first time, a systematic comparison of normal, abnormal, and remote bonding modes is presented. X-ray structural and C-13 NMR data indicate the importance of carbenoid mesomeric contributions in their compound class.. The catalytic performance of the palladium complexes trans-(pyridylidene)Pd(PPh3)(2)Cl as precursors in Suzuki-Miyaura-type cross-coupling suggests a correlation of remote bonding with catalyst robustness and effectivity. When metal precursors M(PPh3)(4) are reacted with 2,4-dichloropyridinium salts, preferential formation of remote carbene complexes occurs and indications are that electronic parameters rather than steric influences are responsible for the observed selectivity. Calculations at the BP86/TZ2P level of theory support interpretation of the results.

  DOI：

  10.1021/om100431u

文献信息

• Pyridine-Derived N-Heterocyclic Carbenes: An Experimental and Theoretical Evaluation of the Bonding in and Reactivity of Selected Normal and Abnormal Complexes of Nickel(II) and Palladium(II)
  作者：Elzet Stander-Grobler、Oliver Schuster、Greta Heydenrych、Stephanie Cronje、Evangeline Tosh、Martin Albrecht、Gernot Frenking、Helgard G. Raubenheimer

  DOI：10.1021/om100431u

  日期：2010.11.22

  We report a thorough investigation of a series of isomeric complexes with the general formula trans-(pyridylidene)M(PPh3)(2)Cl (M = Pd, Ni). For the first time, a systematic comparison of normal, abnormal, and remote bonding modes is presented. X-ray structural and C-13 NMR data indicate the importance of carbenoid mesomeric contributions in their compound class.. The catalytic performance of the palladium complexes trans-(pyridylidene)Pd(PPh3)(2)Cl as precursors in Suzuki-Miyaura-type cross-coupling suggests a correlation of remote bonding with catalyst robustness and effectivity. When metal precursors M(PPh3)(4) are reacted with 2,4-dichloropyridinium salts, preferential formation of remote carbene complexes occurs and indications are that electronic parameters rather than steric influences are responsible for the observed selectivity. Calculations at the BP86/TZ2P level of theory support interpretation of the results.
• Quinolin-4(1<i>H</i>)-imines are Potent Antiplasmodial Drugs Targeting the Liver Stage of Malaria
  作者：Tiago Rodrigues、Filipa P. da Cruz、Maria J. Lafuente-Monasterio、Daniel Gonçalves、Ana S. Ressurreição、Ana R. Sitoe、Maria R. Bronze、Jiri Gut、Gisbert Schneider、Maria M. Mota、Philip J. Rosenthal、Miguel Prudêncio、Francisco-Javier Gamo、Francisca Lopes、Rui Moreira

  DOI：10.1021/jm400246e

  日期：2013.6.13

  We present a novel series of quinolin-4(1H)-imines as dual-stage antiplasmodials, several-fold more active than primaquine in vitro against Plasmodium berghei liver stage. Among those, compounds 5g and 5k presented low nanomolar IC50 values. The compounds are metabolically stable and modulate several drug targets. These results emphasize the value of quinolin-4(1H)-imines as a new chemotype and their suitable properties for further drug development.