2-methoxyphenyldi(3-methylindol-2-yl)methane | 626253-46-1

• 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: 2-methoxyphenyldi(3-methylindol-2-yl)methane
• 英文别名: 2-[(2-methoxyphenyl)-(3-methyl-1H-indol-2-yl)methyl]-3-methyl-1H-indole
• CAS: 626253-46-1
• 化学式: C₂₆H₂₄N₂O
• 分子量: 380.489
• InChiKey: DPCJHSFWMNNFMT-UHFFFAOYSA-N

物化性质

• 沸点：
  610.6±55.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  40.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methoxyphenyldi(3-methylindol-2-yl)methane 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40%的产率得到(2-CH3OC6H4)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
• 作为产物：
  描述：

  3-甲基吲哚 、 邻甲氧基苯甲醛 以 乙醇 为溶剂， 反应 0.05h， 以100%的产率得到2-methoxyphenyldi(3-methylindol-2-yl)methane
  参考文献：
  名称：

  Synthesis of aryl/alkyl(2,2′-bis-3-methylindolyl)methanes and aryl(3,3′-bis indolyl)methanes promoted by secondary amine based ionic liquids and microwave irradiation

  摘要：

  Aryl/alkyl(2,2'-bis-3-methylindolyl)methanes and aryl(bis-3,3'-indolyl)methanes are synthesized in high yield using ionic liquids mediated by microwave. Reaction conditions and product recovery are simple and ionic liquids could be recycled. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.06.106

文献信息

• Deprotonated diindolylmethanes as dianionic analogues of scorpionate bis(pyrazolyl)borate ligands: synthesis and structural characterization of representative titanocene and zirconocene complexes
  作者：Mark R. Mason、Doug Ogrin、Bassam Fneich、Thomas S. Barnard、Kristin Kirschbaum

  DOI：10.1016/j.jorganchem.2004.09.003

  日期：2005.1

  Deprotonation of di(3-methylindol-2-yl)phenylmethane (L2H2) or 2-methoxyphenyldi(3-methylindol-2-yl)methane(L2′H2) with two equivalents of nBuLi, followed by reactions with Cp2TiCl2 or Cp2ZrCl2 yielded complexes Cp2TiL2(1),Cp2TiL2′(2),Cp2ZrL2(3)andCp2ZrL2′(4). Compounds 1–4 were characterized by NMR spectroscopy, and compounds 1, 3, and 4 were further analyzed by X-ray crystallography and elemental

  用两个当量的n BuLi对二（3-甲基吲哚-2-基）苯基甲烷（L 2 H 2）或2-甲氧基苯基二（3-甲基吲哚-2-基）甲烷（L2'H2）进行质子化，然后与Cp反应2 TiCl 2或Cp 2 ZrCl 2产生络合物Cp2TiL2（1），Cp2TiL2'（2），Cp2ZrL2（3）和Cp2ZrL2'（4）。化合物1 - 4通过NMR光谱进行表征，和化合物1，3和4是由X-射线晶体学，元素分析进一步分析。的分子结构1，3，及图4说明螯合的二（3-甲基吲哚-2-基）甲烷与配位的双（吡唑基）硼酸酯具有结构关系。
• Synthesis and Structure of a Bis(indolyl)-Coordinated Titanium Diamido Complex, and Its Catalytic Applications in the Intermolecular Hydroamination of Alkynes
  作者：Shun Ohta、Masaya Shimbayashi、Ryo Miyamoto、Masaaki Okazaki

  DOI：10.1246/bcsj.20180181

  日期：2018.11.15

  Titanium bis(diethylamido) complex 1, which contains a carbon-bridged bis(indolyl) ligand, was obtained in 69% yield from the reaction of Ti(NEt2)4 with the corresponding bis(indole) ligand. Its mo...

  通过 Ti(NEt2)4 与相应的双（吲哚）配体的反应，以 69% 的产率获得钛双（二乙基酰胺）配合物 1，它含有一个碳桥联的双（吲哚基）配体。它的摩...
• Synthesis, Structures, and Solution Dynamics of Titanium and Zirconium Complexes Carrying a Bis(indolyl) and Two Diethylamido Ligands
  作者：Shun Ohta、Shiona Takahashi、Amon Takenaka、Yuta Akazawa、Ryo Miyamoto、Masaaki Okazaki

  DOI：10.1021/acs.inorgchem.9b02566

  日期：2019.11.18

  structures of titanium and zirconium complexes that carry deprotonated 2,2′-bis(indolyl)methane ligands (henceforth: bis(indolyl) ligands) and two diethylamido ligands. We found that the coordination geometry of the indolyl nitrogen atom in such bis(indolyl) ligands is affected by the steric impact of the substituents attached to the central aromatic ring. Moreover, we examined the dynamics of such bis(indolyl)

  吲哚基是从吲哚的NH基团去质子化而获得的阴离子物质。携带吲哚基多齿配体的第4组过渡金属配合物由于π供电和吸电子性弱以及碱度低，代表了很有希望的均相催化剂，例如用于烯烃聚合，加氢胺化和固氮反应吲哚基。在这项研究中，我们系统地研究了带有去质子化的2,2'-双（吲哚基）甲烷配体（以下称双（吲哚基）配体）和两个二乙基酰胺基配体的钛和锆配合物的合成和结构。我们发现在这样的双（吲哚基）配体中的吲哚基氮原子的配位几何形状受连接到中心芳环上的取代基的空间影响。而且，我们研究了相应的锆配合物溶液中此类双（吲哚基）配体的动力学，并结合DFT计算讨论了该机理。这项研究的结果表明，双（吲哚基）配体也可以用作配位柔性辅助配体，并表明了从双（吲哚基）扩展为双（吲哚基）供体配体的可行性。
• ——
  作者：Mark R. Mason、Thomas S. Barnard、Mawuto F. Segla、Baohan Xie、Kristin Kirschbaum

  DOI：10.1023/a:1024234618248

  日期：——

  4-Bromophenyldi(3-methylindol-2-yl)methane (2) and 2-methoxyphenyldi(3-methylindol-2-yl) methane (3) were prepared by sulfuric-acid-catalyzed reactions of 3-methylindole with 4-bromobenzaldehyde and o-anisaldehyde, respectively. Di(3-methylindol-2yl)phenylmethane (1) and tri(3-methylindol-2-yl)methane (4) were similarly prepared as described previously. Spectroscopic data (H-1, C-13 NMR) and the X-ray crystal structures for 1.C2H5OH and 2-4 are reported. The molecular structure of 1.C2H5OH shows hydrogen bonding of both indolyl NH protons to the oxygen of an ethanol molecule. Crystal data for 1.C2H5OH.Orthorhombic, Pca2(1), a = 23.9782(17) Angstrom, b = 8.4437(7) Angstrom, c = 11.3029(9) Angstrom, V = 2288.4(3) Angstrom(3), R-1 = 0.0597. Crystal data for 2.Orthorhombic, P2(1)2(1)2(1), a = 8.911(3) Angstrom, b = 9.584(4) Angstrom, c = 24.040(11) Angstrom, V = 2053.0(14) Angstrom(3), R1 = 0.0454. Crystal data for 3.Monoclinic, P2(1)/c, a = 9.737(2) Angstrom, b = 25.035(6) Angstrom, c = 9.359(2) Angstrom, beta = 114.853(4)degrees, V = 2070.2(8) Angstrom(3), R-1 = 0.0511. Crystal data for 4.Trigonal, R3, a = 14.2214(10) Angstrom, c = 9.6190(10) Angstrom, V = 1684.8(2) Angstrom(3), R-1 = 0.0425.