2-(1-pyrenyl)benzoic acid | 1108178-83-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 2-(1-pyrenyl)benzoic acid
• 英文别名: 2-Pyren-1-ylbenzoic acid；2-pyren-1-ylbenzoic acid
• CAS: 1108178-83-1
• 化学式: C₂₃H₁₄O₂
• 分子量: 322.363
• InChiKey: VLJCXAMNYPDXED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(2-溴苯基)芘 、 二氧化碳 在 正丁基锂 、 盐酸 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.08h， 以58%的产率得到2-(1-pyrenyl)benzoic acid
  参考文献：
  名称：

  Synthesis and crystal structures of fluorescent receptors for 9-butyladenine

  摘要：

  Two pyrene containing fluorescent receptors, 2-(1-pyrenyl)benzoic acid (FR-1) and 8-(1-pyrenyl)-1-naphthoic acid (FR-2), have been designed and synthesized to mimic a pyrene dinucleotide for molecular recognition of 9-butyladenine (9-BuA). The X-ray crystal structures of the receptors FR-1 and FR-2 along with the binding substrate 9-BuA have been determined. FR-1 has the carboxyl group in the same plane as the phenyl group whereas the pyrenyl group is perpendicular to the phenyl group. However, both carboxyl and pyrenyl groups in FR-2 are parallel to each other but perpendicular to the naphthyl group. The binding constant for FR-2 to 9-BuA was found to be 7896 +/- 2187 M-1, which is 8.3-fold greater than that for FR-1 (953 +/- 129 M-1). The results indicate that the complex of 9-BuA with FR-2 is more stable than that with FR-1 by 1.2 kcal/mol. In addition, the molecular recognition of 9-BuA with the receptors can also be observed using fluorescence spectroscopy. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.10.041

文献信息

• Synthesis and crystal structures of fluorescent receptors for 9-butyladenine
  作者：Bassam Lamale、William P. Henry、Lee M. Daniels、Cungen Zhang、Suzane M. Klein、Yu Lin Jiang

  DOI：10.1016/j.tet.2008.10.041

  日期：2009.1

  Two pyrene containing fluorescent receptors, 2-(1-pyrenyl)benzoic acid (FR-1) and 8-(1-pyrenyl)-1-naphthoic acid (FR-2), have been designed and synthesized to mimic a pyrene dinucleotide for molecular recognition of 9-butyladenine (9-BuA). The X-ray crystal structures of the receptors FR-1 and FR-2 along with the binding substrate 9-BuA have been determined. FR-1 has the carboxyl group in the same plane as the phenyl group whereas the pyrenyl group is perpendicular to the phenyl group. However, both carboxyl and pyrenyl groups in FR-2 are parallel to each other but perpendicular to the naphthyl group. The binding constant for FR-2 to 9-BuA was found to be 7896 +/- 2187 M-1, which is 8.3-fold greater than that for FR-1 (953 +/- 129 M-1). The results indicate that the complex of 9-BuA with FR-2 is more stable than that with FR-1 by 1.2 kcal/mol. In addition, the molecular recognition of 9-BuA with the receptors can also be observed using fluorescence spectroscopy. (C) 2008 Elsevier Ltd. All rights reserved.