1-di(pyrrole-2-yl)methyladamantane | 959429-36-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-di(pyrrole-2-yl)methyladamantane
• 英文别名: 1-[di(pyrrol-2-yl)methyl]adamantane；2-[1-adamantyl(1H-pyrrol-2-yl)methyl]-1H-pyrrole
• CAS: 959429-36-8
• 化学式: C₁₉H₂₄N₂
• 分子量: 280.413
• InChiKey: QDLDFQUPAQLLRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  31.6
• 氢给体数：
  2
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-di(pyrrole-2-yl)methyladamantane 、 四丁基醋酸铵 以 氘代氯仿 为溶剂， 生成
  参考文献：
  名称：

  Anion recognition through hydrogen bonding by adamantane-dipyrromethane receptors

  摘要：

  Adamantane-dipyrromethane (AdD) receptors [di(pyrrole-2-yl)methyladamantane (1), 2,2-di(pyrrole-2-yl)adamantane (2). 1,3-bis[di(pyrrole-2-yl)methyl]adamantane (3). 2,2,6,6-tetra(pyrrole-2-yl)adamantane (4)] form complexes with F-, Cl-, Br-, AcO-, NO3-, HSO4-, and H2PO4- The association constants of the complexes were determined by H-1 NMR titrations, whereas the geometries of complexes 1 F- (2 1), 2 F- (2 1), 2 Cl- (2 1), 2 AcO- (2 1), and 4 F- (1 1) were determined by X-ray structural analysis The most stable complexes are of 2 1 stoichiometry with F- and AcO- The stability constants are in accordance with the anion basicity and the ability of AdD receptors to place the hydrogen bonding donor groups in a tetrahedral fashion around anions The binding energies of the complexes between receptors 1-4 and F- anion are calculated using quantum chemical methods The calculated results show that the solvent polarity is important for the complexation of fluoride ion with AdD receptors 1-4 (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tet.2010.01.018
• 作为产物：
  描述：

  吡咯 、 1-金刚烷甲醛 在 三氟乙酸 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 1.0h， 生成 1-di(pyrrole-2-yl)methyladamantane
  参考文献：
  名称：

  Anion recognition through hydrogen bonding by adamantane-dipyrromethane receptors

  摘要：

  Adamantane-dipyrromethane (AdD) receptors [di(pyrrole-2-yl)methyladamantane (1), 2,2-di(pyrrole-2-yl)adamantane (2). 1,3-bis[di(pyrrole-2-yl)methyl]adamantane (3). 2,2,6,6-tetra(pyrrole-2-yl)adamantane (4)] form complexes with F-, Cl-, Br-, AcO-, NO3-, HSO4-, and H2PO4- The association constants of the complexes were determined by H-1 NMR titrations, whereas the geometries of complexes 1 F- (2 1), 2 F- (2 1), 2 Cl- (2 1), 2 AcO- (2 1), and 4 F- (1 1) were determined by X-ray structural analysis The most stable complexes are of 2 1 stoichiometry with F- and AcO- The stability constants are in accordance with the anion basicity and the ability of AdD receptors to place the hydrogen bonding donor groups in a tetrahedral fashion around anions The binding energies of the complexes between receptors 1-4 and F- anion are calculated using quantum chemical methods The calculated results show that the solvent polarity is important for the complexation of fluoride ion with AdD receptors 1-4 (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tet.2010.01.018

文献信息

• Adamantane-Dipyrromethane Derivatives, Method Of Preparation And Applications In Anion Sensing
  申请人：Basaric Nikola

  公开号：US20100069648A1

  公开（公告）日：2010-03-18

  Aamantane dipyrromethane derivatives are obtained by reacting adamantane carbonyl derivatives with pyrrole or pyrrole derivative, in the presence of acid. Adamantane-dipyrromethanes are used to bind anions of the group consisting of: F—, Cl—, Br—, acetate, HSO4— NO3—, and H2PO4—, and particularly F—.

  Aamantane dipyrromethane衍生物是通过在酸的存在下，将金刚烷羰基衍生物与吡咯或吡咯衍生物反应而得到的。金刚烷-二吡咯甲烷被用于结合以下阴离子组：F—，Cl—，Br—，醋酸盐，HSO4—，NO3—和H2PO4—，尤其是F—。
• Synthesis, structural characterization, and anion binding ability of sterically congested adamantane-calix[4]pyrroles and adamantane-calixphyrins
  作者：Marija Alešković、Ivan Halasz、Nikola Basarić、Kata Mlinarić-Majerski

  DOI：10.1016/j.tet.2009.01.007

  日期：2009.3

  Novel adamantane derivatives of calix[4]pyrroles 4-8 and calixphyrin 9 have been synthesized. The structure of 8 has been characterized by X-ray powder diffraction and the structure of 9 by single crystal X-ray analysis. Whereas calixphyrin 9 does not bind anions, analogous calyx[4]pyrrole 8 forms a complex with Cl in the DMSO Solution and in the solid state. The solid state complexation has been accomplished on grinding in a mill, which is the first example of complex formation with an anion in the solid state. (C) 2009 Elsevier Ltd. All rights reserved.
• Adamantane–dipyrromethanes: novel anion receptors
  作者：Marija Renić、Nikola Basarić、Kata Mlinarić-Majerski

  DOI：10.1016/j.tetlet.2007.08.122

  日期：2007.10

  New adamantane-dipyrromethanes (AdD 1-4) were synthesized and their anion binding properties investigated. AdD 1-3 form 2:1 complexes with F- (AdD: F = 2:1) characterized by high association constants, and 1:1 complexes with Cl-, Br-, HSO4- and H2PO4-. The binding of Cl-, Br-, HSO4- and H2PO4- by AdD 1-3 is 2-3 times stronger than for the reference compound, ineso-phenyldipyrromethane (5). However, AdD 4 forms complexes with F- characterized by 1:1 and 1:2 stoichiometry (AdD:F = 1:2). (C) 2007 Elsevier Ltd. All rights reserved.
• WO2008/114067
  申请人：——

  公开号：——

  公开（公告）日：——
• ADAMANTANE-DIPYRROMETHANE DERIVATIVES, METHOD OF PREPARATION AND APPLICATIONS IN ANION SENSING
  申请人：RUDER BOSKOVIC INSTITUTE

  公开号：EP2129656A1

  公开（公告）日：2009-12-09