4-coronen-1-yl-butyric acid | 14890-20-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 4-coronen-1-yl-butyric acid
• 英文别名: 4-coronenyl butyric acid；4-coronenylbutyric acid；4-coronenyl-butyric acid；4-Coronenyl-buttersaeure；4-coronen-1-ylbutanoic acid
• CAS: 14890-20-1
• 化学式: C₂₈H₁₈O₂
• 分子量: 386.45
• InChiKey: BHCZFQZUBXOUJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-coronen-1-yl-butyric acid 在 sodium chloride 、 zinc(II) chloride 作用下， 生成 苯并(a)晕苯
  参考文献：
  名称：

  314. 1：2-苯并香豆烯和萘（2'：3'-1：2）

  摘要：

  DOI：

  10.1039/jr9580001577
• 作为产物：
  描述：

  晕苯 在 aluminum (III) chloride 、 sodium hydroxide 、 肼 作用下， 以 硝基苯 、 二乙二醇 为溶剂， 反应 9.0h， 生成 4-coronen-1-yl-butyric acid
  参考文献：
  名称：

  Improvement of Thermal Stability of Gold Nanoparticles by Synergistic Interligand Interactions

  摘要：

  制备了三种含有不同缩合环的配体的新型金纳米颗粒。由于缩合环形成的强配体间相互作用（π-π堆叠），它们的热稳定性明显高于环烷基硫醇包围的典型金纳米颗粒。热稳定性与π-π堆叠强度之间存在清晰的相关性。

  DOI：

  10.1246/cl.2012.708

文献信息

• Arginine magic with new counterions up the sleeve
  作者：Masamichi Nishihara、Florent Perret、Toshihide Takeuchi、Shiroh Futaki、Adina N. Lazar、Anthony W. Coleman、Naomi Sakai、Stefan Matile

  DOI：10.1039/b501472g

  日期：——

  The elusive questions how arginine-rich sequences allow peptides and proteins to penetrate cells or to form voltage-gated ion channels are controversial topics of current scientific concern. The possible contributions of exchangeable counterions to these puzzling processes remain underexplored. The objective of this report is to clarify scope and limitations of certain counteranions to modulate cellular uptake and anion carrier activity of oligo/polyarginines. The key finding is that the efficiency of counteranion activators depends significantly on many parameters such as activator–membrane and activator–carrier interactions. This finding is important because it suggests that counteranions can be used to modulate not only efficiency but also selectivity. Specifically, activator efficiencies are found to increase with increasing aromatic surface of the activator, decreasing size of the transported anion, increasing carrier concentration as well as increasing membrane fluidity. Efficiency sequences depend on membrane composition with coronene > pyrene ≫ fullerene > calix[4]arene carboxylates in fluid and crystalline DPPC contrasting to fullerene > calix[4]arene ≈ coronene > pyrene carboxylates in EYPC with or without cholesterol or ergosterol. In HeLa cells, the efficiency of planar activators (pyrene) exceeds that of spherical activators (fullerenes, calixarenes). Polyarginine complexes with pyrene and coronene activators exhibit exceptional excimer emission. Decreasing excimer emission with increasing ionic strength reveals dominant hydrophobic interactions with the most efficient carboxylate activators. Dominance of ion pairing with the inefficient high-affinity sulfate activators is corroborated by the reversed dependence on ionic strength. These findings on activator–carrier and activator–membrane interactions are discussed as supportive of arene-templated guanidinium–carboxylate pairing and interface-directed translocation as possible origins of the superb performance of higher arene carboxylates as activators.

  神秘的问题——富含精氨酸的序列如何使多肽和蛋白质穿透细胞或形成电压门控离子通道——是当前科学界争论的话题。可交换配衡离子对这些令人困惑的过程可能的贡献仍未得到充分探索。本报告的目的是澄清某些配衡离子调节寡精氨酸/聚精氨酸细胞摄取和阴离子载体活性的范围和局限性。关键发现是，配衡离子激活剂的效率显著取决于许多参数，如激活剂–膜和激活剂–载体相互作用。这一发现很重要，因为它表明配衡离子不仅可以调节效率，还可以调节选择性。具体而言，随着活化剂芳香表面的增加、转运阴离子尺寸的减小、载体浓度的增加以及膜流动性的增加，活化剂效率提高。效率序列取决于膜组成，在流体和结晶DPPC中，芘环 > 芘 > 富勒烯 > 杯[4]芳烃羧酸盐与在含或不含胆固醇或麦角甾醇的EYPC中富勒烯 > 杯[4]芳烃 ≈ 芘环 > 芘羧酸盐形成对比。在HeLa细胞中，平面型激活剂（芘）的效率超过球型激活剂（富勒烯、杯芳烃）。与芘和芘环激活剂复合的聚精氨酸表现出卓越的激基缔合物发射。随着离子强度的增加，激基缔合物发射减少，揭示了与最高效的羧酸盐激活剂之间占主导地位的疏水相互作用。通过离子强度依赖性的倒置证实了优势离子配对对于效率较低的高亲和硫酸盐激活剂。这些关于激活剂–载体和激活剂–膜相互作用的发现讨论了作为芳烃模板胍基–羧酸配对的支撑，以及作为较高芳烃羧酸作为激活剂的优异性能可能的界面导向转运起源。
• A novel fluorescent coronenyl-phospholipid analogue for investigations of submicrosecond lipid fluctuations
  作者：Lesley Davenport、Bo Shen、Troy W. Joseph、Michael P. Straher

  DOI：10.1016/s0009-3084(00)00214-0

  日期：2001.2

  (DMPC) for dynamic lipid studies. Fluorescence quenching studies using potassium iodide, together with steady-state emission anisotropy (EA) measurements, confirm that the coronene moiety of the phospholipid adduct resides towards the head group interfacial region of the lipid bilayer. Unique properties of this new fluorescent phospholipid adduct are its long mean fluorescence lifetime (tau av approximately

  合成了一种荧光磷脂衍生物，即溶血卵磷脂酰胆碱的2'-（4-coronenylbutyric）酯，用于亚微秒脂质动力学研究。磷脂衍生物的合成涉及游离co烯的弗瑞德-克来福特（Friedel-Crafts）酰化，然后通过Huang-Minlon还原，得到脂肪酰基衍生物4-co烯基丁酸。通过溶血磷脂酰胆碱通过混合的酸酐中间体实现羧酸的酯化。所得的冠烯基磷脂加合物（Cor-PC）已掺入二豆蔻酰基磷脂酰胆碱（DMPC）的超声单层囊泡中进行动态脂质研究。使用碘化钾进行荧光猝灭研究以及稳态发射各向异性（EA）测量，证实磷脂加合物的冠冕部分位于脂质双层的头基界面区域。这种新的荧光磷脂加合物的独特性质是其长的平均荧光寿命（在14摄氏度下tau av约为112 ns），荧光团的平面对称性及其定义的双层位置。结果，冠冕部分的去极化运动靶向由相对窄的双层分布引起的亚微秒“凝胶-流体”脂质动力学。我们的数据表明，这
• Fluorescent phospholipid analogs and fatty acid derivatives
  申请人：——

  公开号：US05322794A1

  公开（公告）日：1994-06-21

  Fluorescence probes are described comprising coronene fluorophores chemically attached to lipids or membrane-mimetic molecules via hydrocarbon spacers of defined length. Also described is a method for determining lipid packing and dynamics in membranes, a method for estimating hydrodynamic properties of macromolecules and macromolecular complexes, and a method for measuring changes in Ca.sup.+2 concentrations in or near membranes.

  描述了荧光探针，包括通过定义长度的烃间隔化学连接到脂质或类膜分子上的coronene荧光团。还描述了一种确定膜中脂质包装和动力学的方法，一种估算大分子和大分子复合物的流体动力学特性的方法，以及一种测量膜内或附近Ca.sup.+2浓度变化的方法。
• PARTICLE AND NEAR-FIELD OPTICAL WAVEGUIDE
  申请人：Yamada Ko

  公开号：US20100239219A1

  公开（公告）日：2010-09-23

  A particle includes: a metal; and a compound containing a hydrogen-bonding forming group, an absorption group different from the hydrogen-bonding forming group, and an aromatic ring, M representing the metal, A representing the absorption group, B representing the hydrogen-bonding forming group, a representing an integer of 0 or greater, b representing an integer of 0 or greater, c representing an integer of 1 or greater, R1 representing an aromatic ring (a planar ring up to a pi-electron number of 24) and a derivative of the aromatic ring, R2 through R5 representing a hydrogen atom, saturated hydrocarbon, unsaturated hydrocarbon, an ether bond, an ester bond, a cyano group, or derivatives of the substances and bonds, and the compound having a structure expressed by the following chemical formula.

  一种粒子包括：一种金属和一种含有氢键形成基团、不同于氢键形成基团的吸收基团和芳香环的化合物，其中M代表金属，A代表吸收基团，B代表氢键形成基团，a表示大于或等于0的整数，b表示大于或等于0的整数，c表示大于或等于1的整数，R1表示芳香环（平面环，最多具有24个π电子）和芳香环的衍生物，R2到R5表示氢原子、饱和碳氢化合物、不饱和碳氢化合物、醚键、酯键、氰基或上述物质和键的衍生物，并且该化合物具有以下化学式所表示的结构。
• Particle and near-field optical waveguide
  申请人：Yamada Ko

  公开号：US08475685B2

  公开（公告）日：2013-07-02

  A particle includes: a metal; and a compound containing a hydrogen-bonding forming group, an absorption group different from the hydrogen-bonding forming group, and an aromatic ring, M representing the metal, A representing the absorption group, B representing the hydrogen-bonding forming group, a representing an integer of 0 or greater, b representing an integer of 0 or greater, c representing an integer of 1 or greater, R1 representing an aromatic ring (a planar ring up to a pi-electron number of 24) and a derivative of the aromatic ring, R2 through R5 representing a hydrogen atom, saturated hydrocarbon, unsaturated hydrocarbon, an ether bond, an ester bond, a cyano group, or derivatives of the substances and bonds, and the compound having a structure expressed by the following chemical formula.

  一种粒子包括：一种金属；以及一种含有氢键形成基团、吸收基团和芳香环的化合物，其中M代表金属，A代表吸收基团，B代表氢键形成基团，a表示大于或等于0的整数，b表示大于或等于0的整数，c表示大于或等于1的整数，R1代表芳香环（一个平面环，最多有24个π电子）和芳香环的衍生物，R2到R5代表氢原子、饱和碳氢化合物、不饱和碳氢化合物、醚键、酯键、氰基或这些物质和键的衍生物，该化合物具有以下化学式表示的结构。