3,6-phenanthrenedicarboxylic acid | 59795-45-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 3,6-phenanthrenedicarboxylic acid
• 英文别名: phenanthrene-3,6-dicarboxylic acid
• CAS: 59795-45-8
• 化学式: C₁₆H₁₀O₄
• 分子量: 266.253
• InChiKey: KPNSGKVCPJTOSC-UHFFFAOYSA-N

物化性质

• 沸点：
  528.2±30.0 °C(Predicted)
• 密度：
  1.457±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,6-phenanthrenedicarboxylic acid 在 正丁基锂 、 氯化亚砜 、 copper(I) bromide dimethylsulfide complex 作用下， 以 四氢呋喃 、 正己烷 、 正戊烷 为溶剂， 反应 12.5h， 生成 3-{6-[1-tert-butyl-1-hydroxy-3-(2-phenylethynyl-phenyl)-prop-2-ynyl]-phenanthren-3-yl}-4,4-dimethyl-1-(2-phenylethynyl-phenyl)-pent-1-yn-3-ol
  参考文献：
  名称：

  Synthesis and Structures of Diindeno-Fused 1,12-Diphenylbenzo[c]phenanthrene and 1,14-Diphenyl[5]helicene Bearing Severe Helical Twists

  摘要：

  Diindeno-fused 1,12-diphenylbenzo[c] phenanthrene 15 and 1,14-diphenyl[5] helicene 20 were prepared in a four-step synthetic sequence from 2,7-naphthalenedicarboxylic acid and 3,6-phenanthrenedicarboxylic acid, respectively. The X-ray structures of 15 and 20 show that the fused ring systems possess severe helical twists. The rotational barriers of the phenyl substituents were determined by the analysis of temperature-dependent H-1 NMR spectra.

  DOI：

  10.1021/ol063056s
• 作为产物：
  描述：

  diethyl 3,6-phenanthrenedicarboxylate 在 sodium hydroxide 、 水 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以99%的产率得到3,6-phenanthrenedicarboxylic acid
  参考文献：
  名称：

  一些头对头连接的DNA小沟结合剂的合成

  摘要：

  已经制备了一系列首尾相连的杂环氨基酸二聚体，用于研究与DNA小沟结合的亲和力和选择性。合成目标的选择由基于计算机的设计主导。已经包括几种新颖的二羧酸连接基，包括吲哚，菲，芴酮和双苯并噻吩。通过印迹分析与DNA的结合表明对衍生自2,7-二氢菲二羧酸的化合物具有很高的亲和力，并且对包含至少4个AT对的AT富集区域具有主要选择性，但具有跨越两个CG碱基对的能力。

  DOI：

  10.1016/s0040-4020(00)00432-4

文献信息

• Phenanthrene-Derived DNA Hairpin Mimics
  作者：Alfred Stutz、Simon M. Langenegger、Robert Häner

  DOI：10.1002/hlca.200390256

  日期：2003.9

  Self-complementary oligodeoxynucleotides containing 3,6-disubstituted phenanthrenes adopt highly stable, hairpin-like structures. The thermodynamic stability of the hairpin mimics depends on the overall length of the phenanthrene building block. Hairpin loops composed of a phenanthrene-3,6-dicarboxamide and ethylene linkers were found to be optimal. The hairpin mimics are more stable than the analogous

  包含3,6-二取代菲的自互补寡聚脱氧核苷酸采用高度稳定的发夹状结构。发夹模拟物的热力学稳定性取决于菲构成单元的总长度。发现由3，6-菲菲和乙烯连接基组成的发夹环是最佳的。发夹模拟物比包含dT 4或dA 4四环的类似发夹更稳定。模型研究表明，发夹模拟物的热力学稳定性主要是由于菲3,6-菲二甲酰胺菲在DNA双链体的相邻碱基对上的芳香堆积。
• Development of a Series of Cross-Linking Agents that Effectively Stabilize α-Helical Structures in Various Short Peptides
  作者：Kazuhisa Fujimoto、Masaoki Kajino、Masahiko Inouye

  DOI：10.1002/chem.200700843

  日期：2008.1.18

  A series of cross-linking agents of varying rigidity and length were designed to stabilize helical structures in short peptides and were then synthesized. The sequences of the short peptides employed in this study each include two X residues (X=Dap, Dab, Orn, and Lys) at the i/i+4, i/i+7, or i/i+11 positions to provide the sites for cross-linking. These peptides were subjected to reaction with the

  设计了一系列具有不同刚度和长度的交联剂，以稳定短肽中的螺旋结构，然后进行合成。本研究中使用的短肽序列各在i / i + 4，i / i + 7或i / i + 11位置包含两个X残基（X = Dap，Dab，Orn和Lys），以提供用于交叉链接的网站。使这些肽与合成的交联剂反应，并通过圆二色性详细分析所得的交联肽的螺旋含量。对于每种肽类，我们发现与交联剂的组合适用于在5摄氏度下构建高达95％的螺旋度的稳定螺旋结构。我们的方法还可以应用于天然蛋白质（例如，修订版
• DNA Containing Non-Nucleosidic Phenanthrene Building Blocks with Asymmetrical Linkers
  作者：Simon M. Langenegger、Vladimir L. Malinovskii、Daniel Wenger、Sarah Werder、Robert Häner

  DOI：10.1080/15257770701506319

  日期：2007.11.26

  The synthesis and hybridization properties of oligonucleotides containing phenanthrene building blocks with non-nucleosidic linkers of different length are described. It was found that the length of the linkers, as well as the combination of unequal linkers can have a substantial influence on the thermal stability of the modified DNA.
• US3953498A
  申请人：——

  公开号：US3953498A

  公开（公告）日：1976-04-27
• Synthesis and Structures of Diindeno-Fused 1,12-Diphenylbenzo[<i>c</i>]phenanthrene and 1,14-Diphenyl[5]helicene Bearing Severe Helical Twists
  作者：Yanzhong Zhang、Jeffrey L. Petersen、Kung K. Wang

  DOI：10.1021/ol063056s

  日期：2007.3.1

  Diindeno-fused 1,12-diphenylbenzo[c] phenanthrene 15 and 1,14-diphenyl[5] helicene 20 were prepared in a four-step synthetic sequence from 2,7-naphthalenedicarboxylic acid and 3,6-phenanthrenedicarboxylic acid, respectively. The X-ray structures of 15 and 20 show that the fused ring systems possess severe helical twists. The rotational barriers of the phenyl substituents were determined by the analysis of temperature-dependent H-1 NMR spectra.