5-bromo-1,2,3-tris(decyloxy)benzene | 695816-76-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-bromo-1,2,3-tris(decyloxy)benzene
• 英文别名: 5-bromo-1,2,3-tris-decoxybenzene
• CAS: 695816-76-3
• 化学式: C₃₆H₆₅BrO₃
• 分子量: 625.814
• InChiKey: NIWJYARHKGQNSJ-UHFFFAOYSA-N

物化性质

• 沸点：
  623.5±50.0 °C(Predicted)
• 密度：
  1.003±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13.01
• 重原子数：
  40.0
• 可旋转键数：
  30.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-bromo-1,2,3-tris(decyloxy)benzene 在 叔丁基锂 、 硼酸三甲酯 、 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 生成 3,4,5-tri(decyloxy)phenyl boronic acid
  参考文献：
  名称：

  Discotic liquid crystalline materials for potential nonlinear optical applications: synthesis and liquid crystalline behavior of 1,3,5-triphenyl-2,4,6-triazine derivatives containing achiral and chiral alkyl chains at the periphery

  摘要：

  As a novel approach to nonlinear optical materials, new octupolar discotic liquid crystalline materials 1,3,5-triphenyl-2,4,6-triazine derivatives containing achiral alkyl chains (5a) and chiral alkyl chains (5b) at the periphery were synthesized. The former exhibits an ordered hexagonal columnar mesophase, whereas the latter displays a rectangular columnar mesophase. The negative exciton splitting observed in the CD spectrum of a thin film of 5b suggests that it has a left-handed helical structure within the column. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.11.085
• 作为产物：
  描述：

  2,6-二甲氧基苯酚 在 甲醇 、 N-溴代丁二酰亚胺(NBS) 、 三溴化硼 、 sodium hydride 、 potassium carbonate 、 potassium iodide 作用下， 以 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 5-bromo-1,2,3-tris(decyloxy)benzene
  参考文献：
  名称：

  Discotic liquid crystalline materials for potential nonlinear optical applications: synthesis and liquid crystalline behavior of 1,3,5-triphenyl-2,4,6-triazine derivatives containing achiral and chiral alkyl chains at the periphery

  摘要：

  As a novel approach to nonlinear optical materials, new octupolar discotic liquid crystalline materials 1,3,5-triphenyl-2,4,6-triazine derivatives containing achiral alkyl chains (5a) and chiral alkyl chains (5b) at the periphery were synthesized. The former exhibits an ordered hexagonal columnar mesophase, whereas the latter displays a rectangular columnar mesophase. The negative exciton splitting observed in the CD spectrum of a thin film of 5b suggests that it has a left-handed helical structure within the column. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.11.085

文献信息

• Synthesis of oleophilic electron-rich phenylhydrazines
  作者：Aleksandra Jankowiak、Piotr Kaszyński

  DOI：10.3762/bjoc.8.29

  日期：——

  Phenylhydrazines 1 substituted with two or three long-chain alkyl, alkoxy or alkylsulfanyl groups were successfully prepared by acid-induced removal of the Boc group in hydrazides 2. The reaction is carried out with 5 equivalents of TfOH in CF₃CH₂OH/CH₂Cl₂ at −40 °C for 1.5 min. Under these conditions, the deprotected hydrazine 1 is fully protonated, which increases its stability in the reaction medium. The hydrazines were isolated in 60–86% yields and purities >90%. The hydrazides 2 were obtained in 43–71% yields from aryl bromides 5, which were lithiated with t-BuLi and subsequently reacted with di-tert-butyl azodicarboxylate (DTBAD).

  苯基肼1通过酸诱导去除肼酰胺2中的Boc基团，成功地取代了两个或三个长链烷基、烷氧基或烷基硫基团。反应在CF₃CH₂OH/CH₂Cl_{2>中以5当量的TfOH在-40°C下进行1.5分钟。在这些条件下，去保护的肼1被完全质子化，增加了其在反应介质中的稳定性。肼类产物以60-86%的产率和纯度>90%的纯度分离。肼酰胺2以43-71%的产率从芳基溴化物5中获得，该溴化物通过与t-BuLi锂化，然后与双tert-丁基叠氮二羧酸酯（DTBAD）反应得到。}
• Alkyloxy modified pyrene fluorophores with tunable photophysical and crystalline properties
  作者：Andreas Kapf、Hassan Eslahi、Meik Blanke、Marco Saccone、Michael Giese、Marcel Albrecht

  DOI：10.1039/c9nj00652d

  日期：——

  coupling approach. Optical properties such as quantum yields and absorption/emission spectra of the fluorophores were investigated by UV/Vis and fluorescence measurements. Aggregation induced excimer formation of the chromophores in polar solvents and in the solid state was proved by the presence of a characteristic bathochromically shifted emission band and a decrease of the emission capability. These

  通过直接的Sonogashira偶联方法制备了新颖的烷氧基改性的2,7-二叔丁基-4,5,9,10-四（芳基乙炔基）py。通过UV / Vis和荧光测量研究了荧光团的光学性质，例如量子产率和吸收/发射光谱。通过存在特征性的红移的发射带和发射能力的降低，证明了在极性溶剂中和在固态下发色团的聚集诱导的准分子形成。这些结果有力地表明意外地观察到，相邻的芘环的受激准分子的形成不会被引入体积大的防止叔-丁基取代基。单晶X射线和计算分析揭示了molecules分子多聚芳烃的分子堆积中相邻分子的共面排列以及π-π堆积的存在。此外，荧光，DSC和POM测量表明，聚集行为，热特性和结晶特性会受到changing核外围附着的官能团结构变化的显着影响。
• Thermotropic MIDA Boronates as a Case Study for the Role of Dipolar Interactions in Liquid Crystalline Self-Assembly
  作者：Tobias Wöhrle、Rafet Gündemir、Wolfgang Frey、Friederike Knecht、Andreas Köhn、Sabine Laschat

  DOI：10.1002/chem.201605648

  日期：2017.3.23

  decoupled from the MIDA head group. These theoretical findings were supported by IR and Raman spectra as well as by asingle crystal structure analysis of 4‐ethoxyphenyl MIDA boronate. Calculations of the electrostatic potential of the MIDA boronate reveal a special polarity pattern that can support the formation of a two‐dimensional network and is likely to explain the liquid crystalline self‐assembly. The

  合成了一系列带有4-烷氧基，3,4-双烷氧基或3,4,5-三烷氧基苯基取代基的MIDA（N-甲基亚氨基二乙酸）硼酸酯，并通过差示扫描量热法（DSC），偏光光学显微镜对它们的介晶性质进行了表征。 （POM）和X射线衍射（XRD）技术，例如小角度和广角X射线散射（分别为SAXS和WAXS）。大多数衍生物是液晶的。对于单或双烷氧基取代的衍生物，尽管MIDA头基庞大，但C 6链已经诱导了近晶A（SmA）中间相。随着链长的增加，圆柱状六角形（Col h）相取代了双取代系列中的SmA相。对一系列MIDA硼酸盐的量子化学计算表明，B-N键是一个在硼原子上带正电荷而在氮和氧原子上带负电荷的双键。此外，未发现芳基部分和B-N键之间存在π相互作用，因此介晶单元与MIDA头基电子分离。IR和拉曼光谱以及4-乙氧基苯基MIDA硼酸酯的单晶体结构分析为这些理论发现提供了支持。MIDA硼酸酯的静电势的计算揭示了一种特
• Tuning the Magnetic Properties of Columnar Benzo[<i>e</i> ][1,2,4]triazin-4-yls with the Molecular Shape
  作者：Marcin Jasiński、Katarzyna Szymańska、Anita Gardias、Damian Pociecha、Hirosato Monobe、Jacek Szczytko、Piotr Kaszyński

  DOI：10.1002/cphc.201800965

  日期：2019.2.18

  magnetic behavior in the series in transition from half‐disc in 1[0] (antiferromagnetic interactions) to full‐disc geometry in the 1[12] homologue (ferromagnetic interactions with J/kB=+7.5 K). Studies of binary systems revealed that a 1 : 1 mixture of 1[0] and 1[12] exhibits modest stabilization of the Colh phase with an expanded range, and magnetic behavior typical for 1[0] in the rigid phase obtained

  合成了一系列同源的盘状1,3,6-三取代的苯并[ e ] [1,2,4]三嗪-4-基1 [n]，其结构，热，光学，磁和电性质为调查。结果表明，该系列的所有成员均显示具有清澈温度的Col h相，该温度取决于N（1）位置烷氧基链的长度，因此取决于圆盘的形状。粉末XRD和磁数据表明，从1 [0]的半盘（反铁磁相互作用）到1 [12]同源物的全盘几何（铁磁相互作用，从J / kB = + 7.5 K）。二进制系统的研究表明，以1：1的混合物1 [0]和1 [12]显示出适度稳定山口ħ相具有扩展范围，磁性行为典型为1 [0]中的刚性相从所获得的熔化。电学测量表明，混合物和单个化合物中的空穴迁移率约为10 -3  cm 2  V -1  s -1，暗电​​导率约为10 -11  Scm -1。通过用紫外线同时照射，后者可增强多达4倍。
• Dendritic Oligothiophenes Terminated with Tris(alkyloxy)phenylethynyl Tails: Synthesis, Physical Properties, and Self-Assembly
  作者：Chang-Qi Ma、Wojciech Pisula、Cornelia Weber、Xin-Liang Feng、Klaus Müllen、Peter Bäuerle

  DOI：10.1002/chem.201002198

  日期：2011.2.1

  periphery. The first‐generation compounds (3 T‐p‐Ph‐C10 and 6 T‐p‐Ph‐C10) were synthesized by palladium‐catalyzed Sonogashira coupling reactions, whereas the higher generation products were synthesized by palladium‐catalyzed Suzuki coupling reactions in a divergent approach. The optical and electrochemical properties were investigated by UV/Vis absorption, fluorescence spectroscopy, and cyclic voltammetry

  到第三代为止的三维（3D）π共轭树枝状低聚噻吩已在外围被三（癸氧基）苯基乙炔基尾部官能化。第一代化合物（3 T- p -Ph-C10和6 T- p-Ph-C10）是通过钯催化的Sonogashira偶联反应合成的，而更高一代的产品是通过钯催化的Suzuki偶联反应以发散的方式合成的。通过UV / Vis吸收，荧光光谱和循环伏安法研究了光学和电化学性质。结果表明，末端三（烷氧基）苯基乙炔基与分支的低聚噻吩核缀合，产生红移的吸收光谱和荧光光谱，并且相对于树枝状的低聚噻吩核减少了光学带隙。结构研究表明，超分子组织的类型与寡聚噻吩核的大小之间存在密切的关系。第一代化合物3 T- p -Ph-C10和6 T- p‐Ph‐C10以整体状态显示柱状相，这已通过二维广角X射线散射（2D WAXS）测量得到证实。自组装成柱状叠层主要归因于刚性噻吩核与柔性侧链之间的相分离，并通过共轭树枝状低聚噻吩单元之间的较