3,4,5-tri(decyloxy)benzoyl chloride | 122060-80-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4,5-tri(decyloxy)benzoyl chloride
• 英文别名: 3,4,5-Tris(decyloxy)benzoyl chloride；3,4,5-tris-decoxybenzoyl chloride
• CAS: 122060-80-4
• 化学式: C₃₇H₆₅ClO₄
• 分子量: 609.374
• InChiKey: VCLHVYIEFVUYLW-UHFFFAOYSA-N

物化性质

• 沸点：
  658.7±50.0 °C(Predicted)
• 密度：
  0.961±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  15.8
• 重原子数：
  42
• 可旋转键数：
  31
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4,5-tri(decyloxy)benzoyl chloride 在 4-二甲氨基吡啶 、 palladium on carbon 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 4-aminophenyl 3,4,5-tris(decyloxy)benzoate
  参考文献：
  名称：

  Columnar Liquid-Crystalline Phase from a Series of Symmetrical Bent Diphenylamine Derivatives: Synthesis and Characterization

  摘要：

  A series of symmetrical bent-shaped materials with six alkoxy chains at the terminal position has been designed and synthesized. All except one exhibit columnar mesophase behavior. The mesomorphic properties of the compounds have been studied with the help of polaralizing optical microscopy (POM) and differential scanning colorimetry (DSC) experiments.

  DOI：

  10.1080/15421400903568146
• 作为产物：
  描述：

  没食子酸甲酯 在 氯化亚砜 、 potassium carbonate 、 potassium iodide 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 76.0h， 生成 3,4,5-tri(decyloxy)benzoyl chloride
  参考文献：
  名称：

  具有不同间隔长度的半相侧链液晶聚合物的自组织行为

  摘要：

  一种新的和简单的一系列含不同间隔基长度联苯液晶原，4 hemiphasmidic侧链液晶聚甲基丙烯酸- [（3,4,5-十三烷氧基）-1- carbonylbenzoate]联苯ñ -甲基（表示为P- ñ - BP，n = 2、4、6、8和10，n是指间隔基的碳原子数），是通过自由基聚合设计并成功合成的。如由POM，DSC和XRD结果，P-2-BP和P-4-BP表现出的六角柱状（Φ ħ）在室温下的阶段，但对于P-4-BP，有从Φ过渡H1相向高度有序的Φh2各向同性之前的相。用更长的间隔基，P-6-BP和P-8-BP在室温下形成近晶相，并转化成Φ ħ在较高温度相。对于P-10-BP，它仅显示从近晶相到各向同性状态的单个过渡。可以归因于这样的事实，即P- n- BP的自组织机制在不同温度下随着间隔物长度的变化而不同。

  DOI：

  10.1039/c7nj00991g

文献信息

• Molecular Factors Responsible for the Formation of the Axially Polar Columnar Mesophase ColhPA
  作者：Joanna Matraszek、Jozef Mieczkowski、Damian Pociecha、Ewa Gorecka、Bertrand Donnio、Daniel Guillon

  DOI：10.1002/chem.200601192

  日期：2007.4.16

  of hexacatenar bent-shape molecules has been systematically modified in order to determine the main molecular factors responsible for the appearance of the axially polar columnar mesophase. It was found that the stability of the polar phase is very sensitive to the subtle modifications of the molecular shape: the phase is solely preserved if the modification is made at the terminal parts of the mesogenic

  为了确定引起轴向极性柱状中间相出现的主要分子因素，已对六邻苯二酚弯曲形分子的结构进行了系统性的修饰。发现极性相的稳定性对分子形状的细微修饰非常敏感：如果在介晶核的末端部分进行修饰，则仅保留该相，而任何其他修饰都会使相不稳定。可以得出结论，驱动平的超分子盘制成的相与圆锥形单元制成的轴向极性相之间过渡的主要因素是满足紧密堆积条件的能力，以消除相邻分子刚性核之间的空隙。
• Effect of central linkages on mesophase behavior of imidazolium-based rod-like ionic liquid crystals
  作者：Xiaohong Cheng、Fawu Su、Rong Huang、Hongfei Gao、Marko Prehm、Carsten Tschierske

  DOI：10.1039/c2sm06854k

  日期：——

  Two series of phenylbenzylether and benzanilide based rod-like imidazolium bromides and their nonionic precursors, the 1-phenyl-1H-imidazoles have been synthesized and the influence of the number and length of the alkyl chain(s) and the structure of the linking group in the aromatic core (–CH2O–, –COO–, –CONH–) on their mesophase self-assembly in ionic liquid crystalline phases were studied by POM, DSC and XRD. Upon decreasing the length of the N-terminal chain or by enlarging the number and length of the C-terminal chains, the sequence smectic (SmA)–hexagonal columnar (Colhex)–micellar cubic (CubI/Pm3n) was found for the ether based imidazolium salts; while only SmA and Colhex phases were observed for the related amides. The influence of the polarity of the central linkages, namely –CH2O– and –CONH–, on the mesophase structure and stability is discussed and compared with related –COO– connected ILC.

  合成了两系列基于苯基苄醚和苯腈的棒状咪唑鎓溴化物及其非离子前体1-苯基-1H-咪唑，并研究了烷基链的数量和长度以及芳香核心中连接基团（–CH2O–、–COO–、–CONH–）的结构对其在离子液晶相中的介相自组装的影响，采用了偏光显微镜（POM）、差示扫描量热仪（DSC）和X射线衍射（XRD）等技术。当减少N-末端链的长度或增加C-末端链的数量和长度时，对于基于醚的咪唑鎓盐，发现了层状相（SmA）–六角柱状相（Colhex）–胶束立方相（CubI/Pm3n）的序列；而相关的酰胺仅观察到SmA和Colhex相。讨论了中心链接的极性（即–CH2O–和–CONH–）对介相结构和稳定性影响，并与相关的–COO–连接的离子液晶进行了比较。
• Concise Synthesis of [1,1′-Biisoquinoline]-4,4′-diol<i>via</i>a Protecting Group Strategy and Its Application for Potential Liquid-Crystalline Compounds
  作者：Elisabeth Kapatsina、Markus Mateescu、Angelika Baro、Wolfgang Frey、Sabine Laschat

  DOI：10.1002/hlca.200900085

  日期：2009.10

  Williamson etherification (Scheme 4). Slightly modified conditions were applied to the esterification of 4a⋅2 HCl with galloyl chlorides 10a–h as well as etherification of 4a⋅2 HCl with 6‐bromohexyl tris(alkyloxy)benzoates 11b,d–h and [(6‐bromohexyl)oxy]‐substituted pentakis(alkyloxy)triphenylenes 14a–c (Scheme 5). Despite the bulky substituents, the respective target 1,1′‐biisoquinolines 12, 13, and 15

  的[1,1'- biisoquinoline] -4,4'-二醇（4A），其为盐酸盐4A从甲氧基甲基开始两个步骤⋅2盐酸（MOM）保护的1-氯异喹啉8（方案3），打开了进一步获得O-官能化的二异喹啉衍生物的途径。化合物4A ⋅2的HCl与4-（十六烷氧基）苯甲酰氯（酯化图5b），得到相应的二酯3B（方案4），这可能不是由Ni基自偶联介导而得到图6b（方案2）。通过4a的反应，醚衍生物2b可以良好的收率获得。在Williamson醚化条件下，用相应的烷基溴9组成的⋅2HCl （方案4）。略作修改的条件被应用到的酯化4A ⋅2HCl中没食子酰氯化物10A - ħ以及醚化4A ⋅2的HCl与6-溴己基三（烷氧基）苯甲酸11b中，d - ħ和[（6-溴己基）氧基]-取代的五（烷氧基）三亚苯基14a – c（方案5）。尽管有大量取代基，但各自的目标1,1'-双异喹啉12、13和分离出15种，收率为14-86％（表）。
• Impact of Substitution Pattern and Chain Length on the Thermotropic Properties of Alkoxy-Substituted Triphenyl-Tristriazolotriazines
  作者：Thorsten Rieth、Natalie Tober、Daniel Limbach、Tobias Haspel、Marcel Sperner、Niklas Schupp、Philipp Wicker、Stefan Glang、Matthias Lehmann、Heiner Detert

  DOI：10.3390/molecules25235761

  日期：——

  Tristriazolotriazines (TTTs) with a threefold alkoxyphenyl substitution were prepared and studied by DSC, polarized optical microscopy (POM) and X-ray scattering. Six pentyloxy chains are sufficient to induce liquid-crystalline behavior in these star-shaped compounds. Thermotropic properties of TTTs with varying substitution patterns and a periphery of linear chains of different lengths, branching

  通过 DSC、偏光光学显微镜 (POM) 和 X 射线散射制备并研究了具有三重烷氧基苯基取代的三三唑并三嗪 (TTT)。六个戊氧基链足以在这些星形化合物中诱导液晶行为。比较了具有不同取代模式和不同长度的线性链外围、链中分支和燕尾的 TTT 的热致性质。一般来说，这些盘显示出广泛且稳定的热致中间相，切向 TTT 优于径向异构体。研究了烷基链的数量、位置、长度和结构的构效关系。
• Tailoring thermotropic cubic mesophases: amphiphilic polyhydroxy derivatives
  作者：Konstanze Borisch、Siegmar Diele、Petra Göring、Horst Kresse、Carsten Tschierske

  DOI：10.1039/a705359b

  日期：——

  Novel amphiphilic polyhydroxy compounds [N-(3,4-dialkoxybenzoyl)-1-amino-1-deoxy-d-glucitols (glucamides), N-(3,4-dialkoxybenzoyl)-1-deoxy-1-methylamino-d-glucitols, N-(3,4,5-trialkoxybenzoyl)-1-deoxy-1-methylamino-d-glucitols (N-methylgucamides), 1-benzoylaminopropane-2,3-diols, 2-benzoylaminopropane-1,3-diols, 2-(3,4,5-tridodecyloxybenzoylamino)-2-(hydroxymethyl)propane-1,3-diol and (3,4,5-tridodecyloxybenzoyl)bis(2,3-dihydroxypropyl)amine] have been synthesized. Their thermotropic liquid crystalline phases were investigated by means of polarizing microscopy, differential scanning calorimetry and X-ray diffraction. Depending on the chain length, and the size of the hydrophilic polyhydroxy units, different mesophases have been found: smectic A phases (SA), inverted bicontinuous cubic phases (CubV2 , Ia3d), hexagonal columnar phases (ColH2) and micellar cubic mesophases (CubI2 , Pn3m or P43n). In strong analogy to lyotropic systems, the type of thermotropic mesophase depends on the ratio between the volume of the lipophilic moiety and the surface area of the hydrophilic moiety at the hydrophilic–lipophilic interface. The crossing from zero interface curvature (SA phase) to the finite negative curvature of the inverted cylindrical aggregates of the columnar mesophase takes place via bicontinuous cubic mesophases. The cylindrical aggregates of the columnar mesophase are stable over a rather broad range of variation of the structural parameter. At a certain degree of the size of the lipophilic moiety in respect to the surface area of the hydrophilic group, however, the transition from the hexagonal columnar to a micellar cubic mesophase takes place. On the basis of proton conductivity measurements and from packing considerations we propose that this cubic lattice is built up by eight closed micelles per unit cell which have a rod-like shape and represent small segments of extended columns. Therefrom we can propose a model for the transformations between these different thermotropic mesophases.

  新型两亲聚羟基化合物[N-(3,4-二烷氧基苯甲酰)-1-氨基-1-脱氧-d-葡萄糖醇（葡萄糖酰胺）、N-(3,4-二烷氧基苯甲酰)-1-脱氧-1-甲基氨基-d-葡萄糖醇、N-(3,4,5-三烷氧基苯甲酰)-1-脱氧-1-甲基氨基-d-葡萄糖醇（N-甲基葡萄糖酰胺）、1-苯甲酰氨基-丙烷-2,3-二醇、2-苯甲酰氨基-丙烷-1,3-二醇、2-(3,4,5-三十二烷氧基苯甲酰氨基)-2-(羟甲基)丙烷-1,3-二醇以及(3,4,5-三十二烷氧基苯甲酰)双(2,3-二羟基丙基)胺]已被合成。通过偏光显微镜、差示扫描量热法和X射线衍射法研究了它们的热致液晶相。根据链长和亲水性聚羟基单元的大小，发现了不同的介相：斜方相（SA）、倒置双连续立方相（CubV2，Ia3d）、六角柱相（ColH2）和胶束立方介相（CubI2，Pn3m或P43n）。与液晶系统非常相似，热致介相的类型取决于亲脂部分的体积与亲水部分在亲水-亲脂界面的表面积之间的比率。从零界面曲率（SA相）到柱状介相的有限负曲率倒置圆柱聚集体的过渡，通过双连续立方介相进行。柱状介相的圆柱聚集体在结构参数变化的较宽范围内是稳定的。然而，在亲脂部分与亲水基团表面积的某个比率下，发生从六角柱相到胶束立方介相的转变。根据质子导电性测量和包装考虑，我们提出该立方格子由每个单元格的八个闭合胶束构成，这些胶束呈杆状，代表扩展柱的小段。由此，我们可以提出一个不同热致介相之间转变的模型。