rac-N,N'-di(6-methylpyridin-2-yl)-2,2'-diaminobinaphthalene | 858941-43-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: rac-N,N'-di(6-methylpyridin-2-yl)-2,2'-diaminobinaphthalene
• 英文别名: N-[(6-methylpyridin-2-yl)methyl]-1-[2-[(6-methylpyridin-2-yl)methylamino]naphthalen-1-yl]naphthalen-2-amine
• CAS: 858941-43-2
• 化学式: C₃₄H₃₀N₄
• 分子量: 494.639
• InChiKey: RZRKRCIXWGYPKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  49.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  rac-N,N'-di(6-methylpyridin-2-yl)-2,2'-diaminobinaphthalene 以 甲苯 为溶剂， 生成 [(rac-N,N'-di(6-methylpyridin-2-yl)-2,2'-diaminobinaphthalene(-2H))ZrCl2]
  参考文献：
  名称：

  Synthesis, Characterization, and Activation of Zirconium and Hafnium Dialkyl Complexes that Contain a C₂-Symmetric Diaminobinaphthyl Dipyridine Ligand

  摘要：

  The diamine rac-H-2[MepyN] (rac-N,N'-di(6-methylpyridin-2-yl)-2,2'-diaminobinaphthalene) has been prepared in good yield through reductive amination of rac-2,2'-diaminobinaphthalene with 6-methylpyridinecarboxaldehyde. The [MepyN](2-) ligand has been employed to prepare a variety of zirconium and hafnium complexes, [MepyN]MX2 (M = Zr, X = NMe2, Cl, OSO2CF3, CH2CHMe2, CH2Ph; M = Hf, X = NMe2, OSO2CF3, CH2CHMe2). The solid state structures of [MepyN]Zr(CH2Ph)(2), [MepyN]Zr(NMe2)Cl, [MepyN]Hf(CH2CHMe2)(2), and [MepyN]Hf(OSO2CF3)(2) have been determined by X-ray diffraction. Activation of [MepyN]Zr(CH2Ph)(2) and [MepyN]Hf(CH2CHMe2)(2) with various Lewis acids leads to observable cationic alkyls that are not active toward 1-hexene polymerization.

  DOI：

  10.1021/om058007i
• 作为产物：
  描述：

  6-甲基-2-吡啶甲醛 在 sodium tetrahydroborate 、 sodium sulfate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 rac-N,N'-di(6-methylpyridin-2-yl)-2,2'-diaminobinaphthalene
  参考文献：
  名称：

  Enantioselective Hydrogenation of Aromatic Ketones Catalyzed by Ru Complexes of Goodwin−Lions-type sp²N/sp³N Hybrid Ligands R-BINAN-R‘-Py

  摘要：

  Goodwin-Lions-type sp2N/sp3N hybrid ligands R-BINAN-R'-Py possessing a C2 axis binaphthyl skeleton have been designed and synthesized. Combination of the new non-phosphine ligand with Ru(pi-CH2C(CH3)CH2)2(cod) has been revealed to catalyze the hydrogenation of aromatic ketones with high enantioselectivity of up to 99% ee. The reaction proceeds essentially without the need for any bases, but the reactivity is enhanced by the addition of KOt-C4H9 attaining an S/C ratio of up to 10 000. The success should expand the range of possibilities in designing catalysts not only for hydrogenation but also for many other reactions.

  DOI：

  10.1021/ja062451a

文献信息

• Enantioselective Hydrogenation of Aromatic Ketones Catalyzed by Ru Complexes of Goodwin−Lions-type sp²N/sp³N Hybrid Ligands R-BINAN-R‘-Py
  作者：Hanmin Huang、Tomoko Okuno、Kazuomi Tsuda、Masahiro Yoshimura、Masato Kitamura

  DOI：10.1021/ja062451a

  日期：2006.7.1

  Goodwin-Lions-type sp2N/sp3N hybrid ligands R-BINAN-R'-Py possessing a C2 axis binaphthyl skeleton have been designed and synthesized. Combination of the new non-phosphine ligand with Ru(pi-CH2C(CH3)CH2)2(cod) has been revealed to catalyze the hydrogenation of aromatic ketones with high enantioselectivity of up to 99% ee. The reaction proceeds essentially without the need for any bases, but the reactivity is enhanced by the addition of KOt-C4H9 attaining an S/C ratio of up to 10 000. The success should expand the range of possibilities in designing catalysts not only for hydrogenation but also for many other reactions.
• Synthesis, Characterization, and Activation of Zirconium and Hafnium Dialkyl Complexes that Contain a <i>C</i>₂-Symmetric Diaminobinaphthyl Dipyridine Ligand
  作者：Zachary J. Tonzetich、Richard R. Schrock、Adam S. Hock、Peter Müller

  DOI：10.1021/om058007i

  日期：2005.6.20

  The diamine rac-H-2[MepyN] (rac-N,N'-di(6-methylpyridin-2-yl)-2,2'-diaminobinaphthalene) has been prepared in good yield through reductive amination of rac-2,2'-diaminobinaphthalene with 6-methylpyridinecarboxaldehyde. The [MepyN](2-) ligand has been employed to prepare a variety of zirconium and hafnium complexes, [MepyN]MX2 (M = Zr, X = NMe2, Cl, OSO2CF3, CH2CHMe2, CH2Ph; M = Hf, X = NMe2, OSO2CF3, CH2CHMe2). The solid state structures of [MepyN]Zr(CH2Ph)(2), [MepyN]Zr(NMe2)Cl, [MepyN]Hf(CH2CHMe2)(2), and [MepyN]Hf(OSO2CF3)(2) have been determined by X-ray diffraction. Activation of [MepyN]Zr(CH2Ph)(2) and [MepyN]Hf(CH2CHMe2)(2) with various Lewis acids leads to observable cationic alkyls that are not active toward 1-hexene polymerization.