5,12-di-(tert-butyl)-3,10-diphenyl-1,3,4,8,10,11-hexaazatetracyclo[6.6.1.0^2,6.0^9,13]pentadeca-2(6),4,9(13),11-tetraene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5,12-di-(tert-butyl)-3,10-diphenyl-1,3,4,8,10,11-hexaazatetracyclo[6.6.1.0^2,6.0^9,13]pentadeca-2(6),4,9(13),11-tetraene
• 英文别名: PzTB；5,12-Ditert-butyl-3,10-diphenyl-1,3,4,8,10,11-hexazatetracyclo[6.6.1.02,6.09,13]pentadeca-2(6),4,9(13),11-tetraene
• 化学式: C₂₉H₃₄N₆
• 分子量: 466.629
• InChiKey: BNBAYSAWNTZQDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  42.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  双(乙腈)氯化钯(II) 、 5,12-di-(tert-butyl)-3,10-diphenyl-1,3,4,8,10,11-hexaazatetracyclo[6.6.1.0^2,6.0^9,13]pentadeca-2(6),4,9(13),11-tetraene 以 甲醇 为溶剂， 以93%的产率得到Pd₄Cl₈([(C₆H₅)NNC(C(CH₃)3)]2C₇H₆N₂)2
  参考文献：
  名称：

  吡唑基Tröger碱Pd 4 Cl 8（PzTB）2配合物的模型Mizoroki – Heck C – C偶联反应的合成，结构阐明和催化活性

  摘要：

  报道了新颖的钯（II）配合物Pd 4 Cl 8（PzTB）2的合成，其中PzTB是吡唑Tröger的碱基类似物配体。通过光谱和晶体学数据可实现对配合物的完整结构解析，在每个钯原子上均表现出金属大环超分子结构和平面正方形几何形状。该配合物对苯乙烯与某些碘代苯衍生物的Mizoroki – Heck C – C偶合模型也表现出高活性和选择性。

  DOI：

  10.1016/j.jorganchem.2011.02.016
• 作为产物：
  描述：

  5-[N-(1H-benzotriazol-1-ylmethyl)amino]-3-tert-butyl-1-phenylpyrazole 在 silver nitrate 作用下， 以 甲醇 为溶剂， 生成 5,12-di-(tert-butyl)-3,10-diphenyl-1,3,4,8,10,11-hexaazatetracyclo[6.6.1.0^2,6.0^9,13]pentadeca-2(6),4,9(13),11-tetraene
  参考文献：
  名称：

  An unexpected chemical behavior of 5-N-(benzotriazol-1-ylmethyl)amino-3-tert-butyl-1-phenylpyrazole

  摘要：

  A rearrangement product or a pyrazolic Troger's base were unexpectedly obtained when 5-N-(benzotriazol-1-ylmethyl)amino-3-tert-butyl-1-phenylpyrazole was treated with electron-rich alkenes with well protic or Lewis acid catalyst, respectively, when tetrahydropyrazolopyridines were expected according with the benzotriazole methodology. The structure of the products was confirmed by NMR and X-ray diffraction techniques. Mechanisms for their formation are also proposed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01115-2

文献信息

• Synthesis of pyrazole and pyrimidine Tröger's-base analogues
  作者：Rodrigo Abonia、Andrea Albornoz、Hector Larrahondo、Jairo Quiroga、Braulio Insuasty、Henry Insuasty、Angelina Hormaza、Adolfo Sánchez、Manuel Nogueras

  DOI：10.1039/b200862a

  日期：2002.6.27

  Tröger's-base analogues bearing fused pyrazolic or pyrimidinic rings were prepared in acceptable to good yields through the reaction of 3-alkyl-5-amino-1-arylpyrazoles and 6-aminopyrimidin-4(3H)-ones with formaldehyde under mild conditions (i.e., in ethanol at 50 °C in the presence of catalytic amounts of acetic acid). Two key intermediates were isolated from the reaction mixtures, which helped us to suggest a sequence of steps for the formation of the Tröger's bases obtained. The structures of the products were assigned by 1H and 13C NMR, mass spectra and elemental analysis and confirmed by X-ray diffraction for one of the obtained compounds.

  通过 3-烷基-5-氨基-1-芳基吡唑和 6-氨基嘧啶-4(3H)-酮与甲醛在温和条件下（即在乙醇中，50 °C，有催化量的乙酸存在）的反应，制备了带有融合吡唑或嘧啶环的特罗格氏碱类似物，收率可接受至良好。从反应混合物中分离出了两个关键的中间产物，这有助于我们提出特罗格氏碱形成的步骤顺序。通过 1H 和 13C NMR、质谱和元素分析确定了产物的结构，并通过 X 射线衍射确认了其中一种化合物。
• Synthesis, structural elucidation and catalytic activity toward a model Mizoroki–Heck C–C coupling reaction of the pyrazolic Tröger’s base Pd4Cl8(PzTB)2 complex
  作者：Fernando Cuenú、Rodrigo Abonia、Alberto Bolaños、Armando Cabrera

  DOI：10.1016/j.jorganchem.2011.02.016

  日期：2011.5

  The synthesis of a novel palladium (II) complex Pd4Cl8(PzTB)2, where PzTB is a pyrazole Tröger’s base analogue ligand is reported. A complete structure elucidation of the complex was achieved by spectroscopic and crystallographic data, exhibiting a metallomacrocycle supramolecular structure and a planar-square geometry on each palladium atom. This complex exhibited also a high activity and selectivity

  报道了新颖的钯（II）配合物Pd 4 Cl 8（PzTB）2的合成，其中PzTB是吡唑Tröger的碱基类似物配体。通过光谱和晶体学数据可实现对配合物的完整结构解析，在每个钯原子上均表现出金属大环超分子结构和平面正方形几何形状。该配合物对苯乙烯与某些碘代苯衍生物的Mizoroki – Heck C – C偶合模型也表现出高活性和选择性。
• An unexpected chemical behavior of 5-N-(benzotriazol-1-ylmethyl)amino-3-tert-butyl-1-phenylpyrazole
  作者：Rodrigo Abonia、Emerson Rengifo、Jairo Quiroga、Braulio Insuasty、Adolfo Sánchez、Justo Cobo、John Low、Manuel Nogueras

  DOI：10.1016/s0040-4039(02)01115-2

  日期：2002.8

  A rearrangement product or a pyrazolic Troger's base were unexpectedly obtained when 5-N-(benzotriazol-1-ylmethyl)amino-3-tert-butyl-1-phenylpyrazole was treated with electron-rich alkenes with well protic or Lewis acid catalyst, respectively, when tetrahydropyrazolopyridines were expected according with the benzotriazole methodology. The structure of the products was confirmed by NMR and X-ray diffraction techniques. Mechanisms for their formation are also proposed. (C) 2002 Elsevier Science Ltd. All rights reserved.