4,7-dimethoxy-2,9-diethyl-1,10-phenanthroline | 1370406-91-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 4,7-dimethoxy-2,9-diethyl-1,10-phenanthroline
• 英文别名: 2,9-Diethyl-4,7-dimethoxy-1,10-phenanthroline
• CAS: 1370406-91-9
• 化学式: C₁₈H₂₀N₂O₂
• 分子量: 296.369
• InChiKey: KAWZGAIRSYHXEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  44.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4,7-dimethoxy-2,9-dimethyl-1,10-phenanthroline 、 碘甲烷 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 0.5h， 以85%的产率得到4,7-dimethoxy-2,9-diethyl-1,10-phenanthroline
  参考文献：
  名称：

  On Ni Catalysts for Catalytic, Asymmetric Ni/Cr-Mediated Coupling Reactions

  摘要：

  The importance of the Ni catalyst in achieving catalytic asymmetric Ni/Cr-mediated coupling reactions effectively is demonstrated. Six phenanthroline-NiCl2 complexes 1a-c and 2a-c and five types of alkenyl iodides A-E were chosen for the study, thereby demonstrating that these Ni catalysts display a wide range of overall reactivity profiles in terms of the degree of asymmetric induction, geometrical isomerization, and coupling rate. For three types of alkenyl iodides A-C, a satisfactory Ni catalyst(s) was found within 1a-c and 2a-c. For disubstituted (Z)-alkenyl iodide D, 2c was identified as an acceptable Ni catalyst: in terms of the absence of Z --> E isomerization and the degree of asymmetric induction but not in terms of the coupling rate. Two phosphine-based Ni catalysts, [(Me)(3)P](2)center dot NiCl2 and [(cy)(3)P](2)center dot NiCl2, were found to meet all three criteria for D. The bond-forming reaction at the C16-C17 position of palytoxin was used to demonstrate the usefulness of the Ni catalysts thus identified.

  DOI：

  10.1021/ja302177z

文献信息

• [EN] CHROMIUM-MEDIATED COUPLING AND APPLICATION TO THE SYNTHESIS OF HALICHONDRINS<br/>[FR] COUPLAGE INDUIT PAR CHROME ET APPLICATION À LA SYNTHÈSE D'HALICHONDRINES
  申请人：HARVARD COLLEGE

  公开号：WO2016176560A1

  公开（公告）日：2016-11-03

  The present invention provides unified synthesis of the CI -CI 9 building blocks of halichondrins and analogs theoreof using selective coupling of poly-halogenated nucleophiles in chromium-mediated coupling reactions. The present invention also provides a practical and efficient synthesis of C20-C38 building blocks of halichondrins and analogs thereof. Also provided herein are general methods of selective activation and coupling of poly-halogenated analogs with an aldehyde. The provided coupling reactions are selective for halo-enone and halo-acetylenic ketal over vinyl halide and halide attached to a sp hydridized carbon. The provided efficient selective coupling reactions can allow easy access to the CI -CI 9 building blocks and C20-C38 building blocks of halichondrins and analogs thereof with limited or no purification or separation of the intermediates.