(3-CH3C8H4NH)HC(3-CH3C8H4N)2BH | 1352731-76-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (3-CH3C8H4NH)HC(3-CH3C8H4N)2BH
• 英文别名: 10,14-dimethyl-12-(3-methyl-1H-indol-2-yl)-1,3-diaza-2-borapentacyclo[11.7.0.03,11.04,9.015,20]icosa-4,6,8,10,13,15,17,19-octaene
• CAS: 1352731-76-0
• 化学式: C₂₈H₂₄BN₃
• 分子量: 413.33
• InChiKey: RIVDHJIQSJIJHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.16
• 重原子数：
  32.0
• 可旋转键数：
  1.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  25.65
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-[双(3-甲基-1H-吲哚-2-基)甲基]-3-甲基-1H-吲哚 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 以23%的产率得到(3-CH3C8H4NH)HC(3-CH3C8H4N)2BH
  参考文献：
  名称：

  Planar, Three-Coordinate Boron Monohydrides Ligated by Bis(3-methylindolyl)methanes

  摘要：

  Reactions of tris(3-methylindolyl)methane, bis(3-methylindolyl)-2-methoxyphenylmethane, and bis(3-methylindolyl)phenylmethane with THF.BH3 result in hydrogen elimination and yield the corresponding boron monohydride complexes (3-CH3C8H4NH)HC(3-CH3C8H4N)(2)BH (6), (2-CH3OC6H4)HC(3-CH3C8H4N)(2)BH (7), and PhHC(3-CH3C8H4N)(2)BH (8), respectively. Compositions and structures were confirmed by NMR (H-1, B-11, C-13) and IR spectroscopy, elemental analysis, and X-ray crystallography. The molecular structures of 6-8 each possess a trigonal-planar boron atom which resides in the plane of a bidentate diindolylmethane ligand. This planarity, the lack of Lewis acid base complexation in the presence of THF, and the short B-N distances suggest significant N -> B pi it donation. Thermolysis of 6 did not produce the three-coordinate, pyramidal borane HC(3-CH3C8H4N)(3)B or a tripodal, four-coordinate acid base complex, presumably due to the significant B-N pi bonding in 6. The planarity of 6-8 and the isoelectronic relationship of BH to C: suggest that diindolylmethanes may be useful platforms for the preparation of a new family of N-heterocyclic carbenes.

  DOI：

  10.1021/om2006694

文献信息

• Planar, Three-Coordinate Boron Monohydrides Ligated by Bis(3-methylindolyl)methanes
  作者：Bingxu Song、Kristin Kirschbaum、Mark R. Mason

  DOI：10.1021/om2006694

  日期：2012.1.9

  Reactions of tris(3-methylindolyl)methane, bis(3-methylindolyl)-2-methoxyphenylmethane, and bis(3-methylindolyl)phenylmethane with THF.BH3 result in hydrogen elimination and yield the corresponding boron monohydride complexes (3-CH3C8H4NH)HC(3-CH3C8H4N)(2)BH (6), (2-CH3OC6H4)HC(3-CH3C8H4N)(2)BH (7), and PhHC(3-CH3C8H4N)(2)BH (8), respectively. Compositions and structures were confirmed by NMR (H-1, B-11, C-13) and IR spectroscopy, elemental analysis, and X-ray crystallography. The molecular structures of 6-8 each possess a trigonal-planar boron atom which resides in the plane of a bidentate diindolylmethane ligand. This planarity, the lack of Lewis acid base complexation in the presence of THF, and the short B-N distances suggest significant N -> B pi it donation. Thermolysis of 6 did not produce the three-coordinate, pyramidal borane HC(3-CH3C8H4N)(3)B or a tripodal, four-coordinate acid base complex, presumably due to the significant B-N pi bonding in 6. The planarity of 6-8 and the isoelectronic relationship of BH to C: suggest that diindolylmethanes may be useful platforms for the preparation of a new family of N-heterocyclic carbenes.