1-[trans-(2-C5H4N)CH=CPh]-1,2-C2B10H11 | 1337554-35-4

• 英文名称: 1-[trans-(2-C5H4N)CH=CPh]-1,2-C2B10H11
• CAS: 1337554-35-4
• 化学式: C₁₅H₂₁B₁₀N
• 分子量: 323.448
• InChiKey: AFGWQAJFKXYSRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为产物：
  描述：

  盐酸 、 1,2-[Cp2ZrC(2-C5H4N)=CPh]-1,2-C2B10H10 以 水 、 乙酸乙酯 为溶剂， 以89%的产率得到1-[trans-(2-C5H4N)CH=CPh]-1,2-C2B10H11
  参考文献：
  名称：

  Reaction of a Zirconocene–Carboryne Complex with Pyridines: Ligand C–H Activation

  摘要：

  Reactions of Cp2Zr(mu-Cl)(mu-C2B10H10)Li(OEt2)(2) (1) with various N-heterocycles derived from pyridine were studied. Treatment of 1 with pyridine, 2-bromopyridine, 2, 4-lutidine, quinoline, and 2-(1-hexynyl)pyridine generated alpha-C-H activation (sigma-bond metathesis) products Cp2Zr(eta(2)-C, N-C5H4N) (sigma-C2B10H11) (2), Cp2Zr[eta(2)-C,N-(6-Br-C5H3N)] (sigma-C2B10H11) (3), Cp2Zr[eta(2)-C,N-(4,6-Me-2-C5H2N)](sigma-C2B10H11) (4), Cp2Zr(eta(2)-C,N-C9H6N)(sigma-C2B10H11) (5), and Cp2Zr-{eta(2)-C,N-[6-((BuC)-Bu-n C)center dot C5H3N]} (sigma-C2B10H11) (7), respectively. On the other hand, reaction of 1 with acridine gave the addition product 1,2-[Cp2Zr(10,9-C13H9N)]-1,2-C2B10H10 (6) in 85% isolated yield. Complex 1 reacted with 3-(1-hexynyl)pyridine to afford alpha-C-H activation species Cp2Zr{eta(2)-C,N-[5-((BuC)-Bu-n C)C5H3N]}(sigma-C2B10H11) (8a) and Cp2Zr{eta(2)-C,N-[3-((BuC)-Bu-n C)C5H3N]}-(sigma-C2B10H11) (8b) in a molar ratio of 42:58, as determined by the H-1 NMR. spectrum. In the presence of CuI, however, the C C insertion products zirconacydopentenes 1,2-[Cp2ZrC(2-C5H4N)=CR]-1,2-C2B10H10 [R = Bu-n (9), Ph (10)] were obtained in 74-77% yields. It is suggested that the coordination of pyridine to the Zr atom is crucial for alpha-C-H activation (sigma-bond metathesis). The presence of CuI can alter the reaction path by preventing the coordination of pyridine to the Zr atom, which blocks the alpha-C-H activation path, leading to the alkyne insertion reaction. All complexes were characterized by H-1, C-13, and B-11 NMR spectra as well as elemental analyses. Their structures were further confirmed by single-crystal X-ray analyses.

  DOI：

  10.1021/om200772q