bis(7-azaindol-1-yl)methane | 476647-18-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: bis(7-azaindol-1-yl)methane
• 英文别名: bis(7-azaindolyl)methane；BAM；1-(Pyrrolo[2,3-b]pyridin-1-ylmethyl)pyrrolo[2,3-b]pyridine
• CAS: 476647-18-4
• 化学式: C₁₅H₁₂N₄
• 分子量: 248.287
• InChiKey: NBPJTLLIGPPOPW-UHFFFAOYSA-N

物化性质

• 熔点：
  140-141 °C
• 沸点：
  482.9±30.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  35.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  bis(7-azaindol-1-yl)methane 以 苯 为溶剂， 生成
  参考文献：
  名称：

  苯并双（N -7-氮杂吲哚基）甲烷的异构铂（II）配合物对CH的活化

  摘要：

  基于双（N -7-氮杂吲哚基）的两个异构和荧光配体，两个同分异构的Pt（II）配合物Pt（L1）（CH 3）2（1a）和Pt（L2）（CH 3）2（2a）合成了甲烷L1（对称）和L2（不对称），并通过NMR和X射线衍射分析对其进行了全面表征。在存在[H（ET 2 O）2 ] [巴' 4 ]（AR'= 3,5-双（三氟甲基）苯基），二者1A和2A能够在环境容易地激活苯C-H键的温度。该产品经苯活化而得图1A和图2a已经分离为[PT（L1）PH（SME 2）] [BAR ' 4 ]（图1b）和[PT（L2）PH（SME 2）] [BAR' 4 ]（图2b）。1b和2b的结构已通过X射线衍射分析确定。在配体的苯基2B结合专门反式到的吡咯氮原子L2。

  DOI：

  10.1021/om0301785
• 作为产物：
  描述：

  7-氮杂吲哚 、 二溴甲烷 在 氢氧化钾 、 四丁基溴化铵 作用下， 以 甲苯 为溶剂， 反应 72.0h， 以56%的产率得到bis(7-azaindol-1-yl)methane
  参考文献：
  名称：

  Isomerism of Bis(7-azaindolyl)methane

  摘要：

  [GRAPHICS]Three isomers of bis(7-azaindolyl)methane have been synthesized and fully characterized. Isomers 1 and 2 contain 7-azaindolyl groups that are bound to the CH2 group through nitrogen atoms. However, 1 contains two "normal" 7-azaindolyl groups, whereas 2 contains both a normal 7-azaindolyl group and a tautomer form of 7-azaindolyl. The third isomer 4 contains two 7-azaindolyl groups that are bound to the CH2 group through the carbon atom at the position-3. These three isomers show distinct absorption and emission spectra, attributable to the different forms of 7-azaindolyl groups in the isomers, as indicated by the results of ab initio calculations.

  DOI：

  10.1021/ol026776h

文献信息

• Impact of the linker groups in bis(7-azaindol-1-yl) chelate ligands on structures and stability of Pt(N,N-L)R2 complexes
  作者：Shu-Bin Zhao、Guo-hui Liu、Datong Song、Suning Wang

  DOI：10.1039/b813501k

  日期：——

  class I ligands by single-crystal X-ray diffraction and 1H NMR spectroscopic analyses. Complexes Pt(1,3-BAPr)Me2 and Pt(1,4-BABu)Me2 have been found to have a poor stability, compared to the 1,2-BAB and BAM analogues. Two geometric isomers of the Pt(BAHE)Ph2 complex have been identified by NMR spectra and the structure of one of the isomers has been determined by X-ray diffraction analysis, establishing

  通式为Pt（N，N -L）R 2的新型有机铂（II）配合物，其中L为双（7-氮杂吲哚-1-基）螯合物配体，R是一个 甲基 或一个 苯基，已合成和研究，目的是为了了解连接基团对L的影响 配体Pt（II）配合物的结构和稳定性的研究。L配体在我们的研究中使用的化合物分为两类：I类，其脂族连接基位于两个7-氮杂吲哚基之间，例如-CH 2-（BAM），-（CH 2）3-（1,3-BAPr）和-（CH 2）4-（1,4-BABu），II类，带有芳香族接头，例如1,2-苯基（1,2-BAB）1,3-苯基（1,3-BAB）和1,4-二氢萘-1,4-环氧（BAHE）。这些新的单核Pt（II）配合物的结构已通过单晶X射线衍射分析。对于1,3-BAPr配体，还获得了具有[Pt（SMe 2）Ph 2 ] 2（1,3-BAPr）分子式的双核配合物，并通过以下方法建立了结构X射线衍射分析。通过使用晶体结构数据，检查了
• Dinuclear Copper(I) Complexes as Precatalysts in Ullmann and Goldberg Coupling Reactions
  作者：Estela Haldón、Eleuterio Álvarez、M. Carmen Nicasio、Pedro J. Pérez

  DOI：10.1021/om900119r

  日期：2009.7.13

  The use of structurally well-characterized copper(I) species as precatalysts in C−N and C−S bond forming reactions is described. Two new dinuclear Cu(I) complexes containing two isomeric ligands of bis(7-azaindolyl)methane have been synthesized and fully characterized by NMR and X-ray diffraction studies. Both copper(I) species exhibit a 1:1 Cu/L ratio and have been used as precatalysts in the N-arylation

  描述了结构良好表征的铜（I）物种在CN和CS键形成反应中作为预催化剂的用途。合成了两个新的包含双（7-氮杂吲哚基）甲烷的两个异构体配体的双核Cu（I）络合物，并通过NMR和X射线衍射研究对其进行了全面表征。两种铜（I）物种均显示出1：1的Cu / L比，并已被用作2-吡咯烷酮的N-芳基化和硫醇与芳基碘化物的S-芳基化的预催化剂。该络合物有效催化这些交叉偶联反应，在温和条件下提供高产率的产物。
• Reactivity of SiMe₃- and SnR₃-Functionalized Bis(7-azaindol-1-yl)methane with [PtR₂(μ-SMe₂)]_<i>n</i> (R = Me, Ph) and the Resulting Pt(II) and Pt(IV) Complexes
  作者：Shu-Bin Zhao、Rui-Yao Wang、Suning Wang

  DOI：10.1021/om900022n

  日期：2009.4.27

  Three new bis(7-azaindol-1-yl)methane (BAM) derivative ligands Me3Si-BAM (1a), Me3Sn-BAM (1b), and Ph3Sn-BAM (1c) have been synthesized, and their reactivities with [PtR2(mu-SMe2)](n), (R = Me, Ph) have been examined. Two Pt(II) complexes Pt(Me3Si-BAM)R-2 (R = Me, 2; Ph, 3) were obtained from the reactions of 1a. The reactions of 1b with [PtR2(mu-SMe2)](n) (R = Me, Ph) produced unexpected novel N,C,N-BAM Pt(IV) complexes Pt(N,C,N-BAM)(SnMe3)R-2 (R = Me, 4; Ph, 6) likely via oxidative cleavage of the C-BAM-Sn bond in 1b. 1c reacted with [PtPh2(mu-SMe2)](n) (n = 2, 3) yielding the anticipated Pt(II) complex Pt(Ph3Sn-BAM)Ph-2 (7), whereas its reaction with [PtMe2(mu-SMe2)](2) resulted in unusual Pt-II-Me and Sn-IV-Ph metathesis, yielding also 7 as one of the products. Mechanistic investigation was carried out to understand this phenomenon. The reactivities of 2 with MeI, MeOTf, and I-2 were examined. Its reaction with I-2 gave rise to Pt(Me3Si-BAM)I-2 (9) along with CH3I, indicating the possibility of functionalizing Pt-II-Me via iodinolysis. The reaction of Pt(NC,N-BAM)(SnMe3)Me-2 (4) with I-2 produced a number of unusual N,C,N-BAM Pt(IV) complexes including Pt(N,C,N-BAM)Me(I)(SnI2Me) (13) and Pt(N,C,N-BAM)Me(I)(I-3) (14) due to the electrophilic cleavage of the Sn-Me, Pt-Me and/or Pt-Sn bond(s) by I-2. For comparison, we also investigated the reaction of Pt(N,C,N-BAM)Me-3 (M1) with I-2 which was found to exhibit a high regioselectivity for the axial Pt-Me group, resulting in Pt(N,C,N-BAM)Me-2(I-3) (15) with the two Pt-Me being cis to each other. The reactions of 4 and M1 with I-2 are rare examples of Pt-IV-CH3 bond cleavage by the elimination of CH3I. The structures of 1a and complexes 2, 7, 9, and 13-15 were determined by X-ray diffraction analyses.
• Isomerism of Bis(7-azaindolyl)methane
  作者：Datong Song、Hartmut Schmider、Suning Wang

  DOI：10.1021/ol026776h

  日期：2002.11.1

  [GRAPHICS]Three isomers of bis(7-azaindolyl)methane have been synthesized and fully characterized. Isomers 1 and 2 contain 7-azaindolyl groups that are bound to the CH2 group through nitrogen atoms. However, 1 contains two "normal" 7-azaindolyl groups, whereas 2 contains both a normal 7-azaindolyl group and a tautomer form of 7-azaindolyl. The third isomer 4 contains two 7-azaindolyl groups that are bound to the CH2 group through the carbon atom at the position-3. These three isomers show distinct absorption and emission spectra, attributable to the different forms of 7-azaindolyl groups in the isomers, as indicated by the results of ab initio calculations.
• Benzene C−H Activation by Two Isomeric Platinum(II) Complexes of Bis(<i>N</i>-7-azaindolyl)methane
  作者：Datong Song、Suning Wang

  DOI：10.1021/om0301785

  日期：2003.5.1

  isomeric Pt(II) complexes, Pt(L1)(CH3)2 (1a) and Pt(L2)(CH3)2 (2a), based on two isomeric and fluorescent ligands of bis(N-7-azaindolyl)methane, L1 (symmetric) and L2 (asymmetric), have been synthesized and fully characterized by NMR and X-ray diffraction analyses. In the presence of [H(Et2O)2][BAr‘4] (Ar‘ = 3,5-bis(trifluoromethyl)phenyl), both 1a and 2a are capable of activating a benzene C−H bond readily

  基于双（N -7-氮杂吲哚基）的两个异构和荧光配体，两个同分异构的Pt（II）配合物Pt（L1）（CH 3）2（1a）和Pt（L2）（CH 3）2（2a）合成了甲烷L1（对称）和L2（不对称），并通过NMR和X射线衍射分析对其进行了全面表征。在存在[H（ET 2 O）2 ] [巴' 4 ]（AR'= 3,5-双（三氟甲基）苯基），二者1A和2A能够在环境容易地激活苯C-H键的温度。该产品经苯活化而得图1A和图2a已经分离为[PT（L1）PH（SME 2）] [BAR ' 4 ]（图1b）和[PT（L2）PH（SME 2）] [BAR' 4 ]（图2b）。1b和2b的结构已通过X射线衍射分析确定。在配体的苯基2B结合专门反式到的吡咯氮原子L2。