4-[10-(3-Hydroxy-3-methyl-but-1-ynyl)-anthracen-9-yl]-2-methyl-but-3-yn-2-ol | 18499-69-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 4-[10-(3-Hydroxy-3-methyl-but-1-ynyl)-anthracen-9-yl]-2-methyl-but-3-yn-2-ol
• 英文别名: 9,10-bis(3-hydroxy-3-dimethyl-1-butynyl)anthracene；9,10-Bis-(3-methyl-3-hydroxybut-1-inyl)-anthracen；9,10-bisdimethylcarbinolethynylanthracene；9,10-bis(3-hydroxy-3-methylbutynyl)anthracene；9,10-bis-(3-hydroxy-3-methyl-but-1-ynyl)-anthracene；9,10-Bis-(3-hydroxy-3-methyl-but-1-inyl)-anthracen；4-[10-(3-Hydroxy-3-methylbut-1-ynyl)anthracen-9-yl]-2-methylbut-3-yn-2-ol
• CAS: 18499-69-9
• 化学式: C₂₄H₂₂O₂
• 分子量: 342.437
• InChiKey: QZLXUSOKVDHEAZ-UHFFFAOYSA-N

物化性质

• 沸点：
  559.3±40.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-[10-(3-Hydroxy-3-methyl-but-1-ynyl)-anthracen-9-yl]-2-methyl-but-3-yn-2-ol 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 9,10-Bis-(3-methyl-3-hydroxybut-1trans-enyl)-anthracen
  参考文献：
  名称：

  Skowronski,R. et al., Bulletin de la Societe Chimique de France, 1967, p. 4235 - 4243

  摘要：

  DOI：
• 作为产物：
  描述：

  9,10-二溴蒽 在 copper(l) iodide 、 正丁基锂 、 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 、 氯代叔丁烷 作用下， 以 四氢呋喃 、 正己烷 、 二乙胺 为溶剂， 反应 71.0h， 生成 4-[10-(3-Hydroxy-3-methyl-but-1-ynyl)-anthracen-9-yl]-2-methyl-but-3-yn-2-ol
  参考文献：
  名称：

  The synthesis of anthracene, and dipyridine salts as cations for DMIT complexes

  摘要：

  The synthesis of a series of cations for the preparation of [Ni(dmit)(2)](2) complexes is described. These cations are a series of 9,10-disubstituted anthracene derivatives with phosphane or alkylamine sustituents. Metal catalysed coupling reactions were used to prepare the 9,10-ethynylanthracene derivatives, one of which was subsequently methylated, using iodomethane as methylating reagent, to form cations for [Ni(dmit)(2)](2) salts. A range of salts were prepared using ferrocene and anthracene-based cations with [Ni(dmit)(2)](2) as the dianion. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.11.007

文献信息

• 1,4-Selective Diels–Alder Reaction of 9,10-Diethynylanthracene with 3,6-Difluorobenzyne
  作者：Yoshitaka Tsuchido、Tomohito Ide、Yuji Suzaki、Kohtaro Osakada

  DOI：10.1246/bcsj.20150017

  日期：2015.6.15

  Diels–Alder reaction of 9,10-bis(3-hydroxy-3-methyl-1-butynyl)anthracene with 3,6-difluorobenzyne yields the naphthobarrelene derivative via 1,4-addition of difluorobenzyne in a higher yield than the 9,10-adduct having a triptycene core. The DFT calculations revealed that the intermediate for the former reaction is stabilized more significantly by attractive interaction between a fluorine atom at the benzyne ring and a hydrogen atom at the anthracene ring.

  9,10-双（3-羟基-3-甲基-1-丁炔基）蒽与3,6-二氟苯乙炔的Diels-Alder反应通过1,4-加成生成萘桶烯衍生物，其产率高于具有三聚氰胺核心的9,10-加成物。DFT计算显示，前一种反应的中间体通过苯乙炔环中的氟原子与蒽环中的氢原子之间的吸引相互作用得到了更显著的稳定。
• Molecular Wires Built from Binuclear Cyclometalated Complexes
  作者：Sandrine Fraysse、Christophe Coudret、Jean-Pierre Launay

  DOI：10.1021/ja0299506

  日期：2003.5.1

  the calculation of the electronic coupling element V(ab). This series of complexes exhibit relatively large couplings when comparing with complexes of similar metal-metal distances, with a special mention for the anthracene-containing spacer, which appears particularly efficient for mediating the metal-metal interaction. The results can be rationalized by theoretical calculations at the extended Hückel

  已经制备了具有 [Ru(bpy)(2)(ppH)](+) 型（bpy = 2,2'-联吡啶，ppH = 2-苯基吡啶）的环金属化末端的双核配合物，由各种间隔基连接。这些间隔基由一个或两个三键或双乙炔基芳基组成，芳基 = 苯、噻吩或蒽。从 [Ru(bpy)(2)(ppBr)](+) 合成子开始，通过 Sonogashira 与合适的双炔烃偶联获得具有双乙炔基芳基间隔基的复合物。从真正的炔烃 [Ru(bpy)(2)(pp-CCH)](+) 环金属化前体中获得具有一个或两个三键的配合物，分别使用 Sonogashira 偶联与碘衍生物 [Ru(bpy)(2) (ppI)](+) 或氧化同源偶联。还获得了一些带有叔丁基取代的联吡啶辅助配体的配合物。双核复合物的氧化发生在 0.5 V 附近，即。例如，比基于 [Ru(bpy)(3)](2+) 的配合物更容易。观察到单个阳极波，几乎没有可检测到的分裂，
• Electronic and Magnetic Communication in Mixed-Valent and Homovalent Ruthenium Complexes Containing Phenylcyanamide Type Bridging Ligands
  作者：Muriel Fabre、Jacques Bonvoisin

  DOI：10.1021/ja067255i

  日期：2007.2.1

  Four new phenylcyanamido-bridge dinuclear ruthenium complexes [Ru(tpy)(thd)}2(mu-L)] with tpy = 2,2':6',2' '-terpyridine, thd = 2,2,6,6-tetramethyl-3,5-heptanedione and L = dcbp = 4,4'-dicyanamidobiphenyl; bcpa = bis(4-cyanamidophenyl)acetylene; bcpda = bis(4-cyanamidophenyl)diacetylene; bcpea = 9,10,-bis(4-cyanamidophenylethynyl)anthracene have been prepared and fully characterized. The mixed valent

  四种新的苯基氰胺桥双核钌配合物 [Ru(tpy)(thd)}2(mu-L)]，tpy = 2,2':6',2''-三联吡啶，thd = 2,2,6， 6-四甲基-3,5-庚二酮和 L = dcbp = 4,4'-二氰氨基联苯；bcpa = 双（4-氰胺基苯基）乙炔；bcpda = 双（4-氰氨基苯基）二乙炔；bcpea = 9,10,-双（4-氰胺基苯基乙炔基）蒽已被制备并充分表征。所有配合物的混合价 Ru(II)Ru(III) 和同价顺磁性 Ru(III)Ru(III) 形式都是电化学生成的，并通过 UV-vis-NIR 和 EPR 光谱进行研究。电子通信通过从近红外区域的间隔测量中提取的电子耦合参数 V(ab) 量化，磁通信通过交换耦合常数 J 量化，当改变温度时，可以从 EPR 信号的强度中获得。获得并讨论了电子和磁耦合与金属间距离的指数衰减。
• One Step Pd(0)-Catalyzed Synthesis, X-ray Analysis, and Photophysical Properties of Cyclopent[<i>hi</i>]aceanthrylene:  Fullerene-like Properties in a Nonalternant Cyclopentafused Aromatic Hydrocarbon
  作者：Hung Dang、Marcia Levitus、Miguel A. Garcia-Garibay

  DOI：10.1021/ja016189b

  日期：2002.1.1

  A simple procedure for the synthesis of cyclopentafused polycyclic aromatic hydrocarbons (CP-PAH) with Pd(PPh(3))(2)Cl(2) catalyst has been applied to the one-pot palladium(0)-catalyzed coupling of 9,10-dibromoanthracene (1) with 2-methyl-3-butyn-2-ol. Reactions carried out in refluxing benzene in the presence of CuSO(4)/Al(2)O(3) yielded 9,10-dialkynylanthracene 2a, alkynyl aceanthrylene 2b, and 2

  一种用 Pd(PPh(3))(2)Cl(2) 催化剂合成环戊稠多环芳烃 (CP-PAH) 的简单方法已应用于一锅钯 (0) 催化偶联 9， 10-二溴蒽 (1) 与 2-methyl-3-butyn-2-ol。在 CuSO(4)/Al(2)O(3) 存在下在回流苯中进行反应，生成 9,10-二炔基蒽 2a、炔基 aceanthrylene 2b 和 2,7-二取代环戊 [hi]aceanthrylene 2c，含量为 13%分别为 23% 和 19% 的纯化产率，总转化率为 80-90%。在 110 摄氏度无铜的密封管反应将 2c 的产率提高到 >75%。2a 和 2c 的单晶 X 射线分析揭示了三维氢键网络，产生了独特的晶体堆积。2b 的堆积结构由两个乙炔分子之间的 pi-pi 堆积相互作用支配。CP-PAHs 2b 和 2c 具有潜在的有趣的类富勒烯光物理学。虽然 2a (Phi(F)
• Novel, yellow-emitting anthracene/fluorene oligomers: synthesis and characterization
  作者：Zujin Zhao、Shuqiang Yu、Lei Xu、Hongbo Wang、Ping Lu

  DOI：10.1016/j.tet.2007.05.095

  日期：2007.8

  A novel series of highly soluble and strongly yellow fluorescent with well-controlled, alternative anthracene, and fluorene units were successfully synthesized by a Pd/Cu-catalyzed Sonogashira coupling reaction and characterized. Their thermal stabilities, electrochemical behaviors, and photophysical properties were investigated. These oligomers might be used as models to study structure-property relationship for their corresponding polymers and applied in optoelectronics devices as materials themselves. (C) 2007 Elsevier Ltd. All rights reserved.