3,5-dichloro-N-[2-[4-(9-methyl-1,10-phenanthrolin-2-yl)butoxy]-6-[(4S)-4-propan-2-yl-4,5-dihydro-1,3-oxazol-2-yl]phenyl]benzenesulfonamide | 1197180-60-1

• 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: 3,5-dichloro-N-[2-[4-(9-methyl-1,10-phenanthrolin-2-yl)butoxy]-6-[(4S)-4-propan-2-yl-4,5-dihydro-1,3-oxazol-2-yl]phenyl]benzenesulfonamide
• CAS: 1197180-60-1
• 化学式: C₃₅H₃₄Cl₂N₄O₄S
• 分子量: 677.651
• InChiKey: ALHFXWAUTUPONM-SSEXGKCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  46
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3,5-二氯苯磺酰氯 、 (S)-2-(4-isopropyl-4,5-dihydrooxazol-2-yl)-6-(4-(9-methyl-1,10-phenanthrolin-2-yl)butoxy)aniline 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 8.0h， 以80%的产率得到3,5-dichloro-N-[2-[4-(9-methyl-1,10-phenanthrolin-2-yl)butoxy]-6-[(4S)-4-propan-2-yl-4,5-dihydro-1,3-oxazol-2-yl]phenyl]benzenesulfonamide
  参考文献：
  名称：

  Dramatic Improvement in Catalyst Loadings and Molar Ratios of Coupling Partners for Ni/Cr-Mediated Coupling Reactions: Heterobimetallic Catalysts

  摘要：

  Two new ligands 1a,b are reported. Upon treatment with 1 equiv of NiCl2 center dot(MeOCH2)(2), 1a,b give the corresponding Ni complexes. X-ray analysis of 1a-NiCl2 established that the NiCl2 is selectively coordinated to the phenanthroline nitrogens. Ni/Cr heterobimetallic catalysts 1a,b center dot CrCl2/NiCl2, prepared from 1a,b center dot NiCl2, have been shown to behave exceptionally well in catalytic asymmetric Ni/Cr-mediated couplings, with highlights including the following: (1) 1-2 mol % catalyst is sufficient to complete the coupling; (2) only negligible amounts of the dimers, byproducts formed through the alkenyl Ni species, are observed; (3) the coupling goes to completion even with a 1:1 molar ratio of the coupling partners; and (4) the asymmetric induction is practically identical with that obtained from the coupling with the Cr catalysts prepared from (S)-sulfonamides 2a,b. The scope of the new Ni/Cr heterobimetallic catalysts was briefly studied using four additional aldehydes. The applicability of the new catalysts to polyfunctional substrates was demonstrated by two C-C bond formations chosen from the hatichondrin/E7389 synthesis as examples.

  DOI：

  10.1021/ja9079308

文献信息

• Dramatic Improvement in Catalyst Loadings and Molar Ratios of Coupling Partners for Ni/Cr-Mediated Coupling Reactions: Heterobimetallic Catalysts
  作者：Xiang Liu、James A. Henderson、Takeo Sasaki、Yoshito Kishi

  DOI：10.1021/ja9079308

  日期：2009.11.25

  Two new ligands 1a,b are reported. Upon treatment with 1 equiv of NiCl2 center dot(MeOCH2)(2), 1a,b give the corresponding Ni complexes. X-ray analysis of 1a-NiCl2 established that the NiCl2 is selectively coordinated to the phenanthroline nitrogens. Ni/Cr heterobimetallic catalysts 1a,b center dot CrCl2/NiCl2, prepared from 1a,b center dot NiCl2, have been shown to behave exceptionally well in catalytic asymmetric Ni/Cr-mediated couplings, with highlights including the following: (1) 1-2 mol % catalyst is sufficient to complete the coupling; (2) only negligible amounts of the dimers, byproducts formed through the alkenyl Ni species, are observed; (3) the coupling goes to completion even with a 1:1 molar ratio of the coupling partners; and (4) the asymmetric induction is practically identical with that obtained from the coupling with the Cr catalysts prepared from (S)-sulfonamides 2a,b. The scope of the new Ni/Cr heterobimetallic catalysts was briefly studied using four additional aldehydes. The applicability of the new catalysts to polyfunctional substrates was demonstrated by two C-C bond formations chosen from the hatichondrin/E7389 synthesis as examples.