3,4,5-tris(3,4,5-tridodecyloxybenzyloxy)benzyl alcohol | 186031-56-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,4,5-tris(3,4,5-tridodecyloxybenzyloxy)benzyl alcohol
• 英文别名: [3,4,5-Tris[(3,4,5-tridodecoxyphenyl)methoxy]phenyl]methanol
• CAS: 186031-56-1
• 化学式: C₁₃₆H₂₄₂O₁₃
• 分子量: 2085.41
• InChiKey: ORVPHOLPPFAKSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  55.4
• 重原子数：
  149
• 可旋转键数：
  118
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  131
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  3,4,5-tris(3,4,5-tridodecyloxybenzyloxy)benzyl alcohol 在 氯化亚砜 、 2,6-二叔丁基吡啶 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到3,4,5-tris[3',4',5'-tris(n-dodecan-1-yloxy)benzyloxy]benzyl chloride
  参考文献：
  名称：

  Rational Design of the First Spherical Supramolecular Dendrimers Self-Organized in a Novel Thermotropic Cubic Liquid-Crystalline Phase and the Determination of Their Shape by X-ray Analysis

  摘要：

  The rational design, the synthesis via a new convergent approach, and the characterization of four generations of monodendrons based on the AB(3) building block methyl 3,4,5-trishydroxybenzoate are described. The first generation monodendrons are crystalline. The second generation methyl 3,4,5-tris-3',4',5'-[tris(n-dodecyloxy)benzyloxy]benzoate (12Gn-AG-CH3, n = 2), the corresponding benzyl alcohol (12G2-AG-CH2OH) and benzoic acid (12G2-AG), and all higher generation monodendrons with n = 3 and 4 exhibit in addition to the crystal phase an isomorphous cubic liquid-crystalline (LC) phase of space group. The cubic unit cell parameters of 12G2-AG, 12G3-AG, and 12G4-AG are 68.3, 79.2, and 84.0 Angstrom, respectively. Computed electron density profiles demonstrated that in the cubic phase 12, 6, and 2 monodendrons of generation 2, 3 and 4 are self-assembled in supramolecular dendrimers resembling spherical micelles when they are centered at the corners and the body-center and respectively highly rounded tetrahedra when they are at 1/4 and 3/4 distance along one of the bisectors of each face of the cubic cell. This novel thermotropic LC phase is similar to that of the lyotropic phase of biological lipids. These supramolecular dendrimers contain a poly(benzyl ether) core dispersed in an aliphatic matrix of nearly uniform density which is made up of the melted terminal long alkyl chains of the monodendrons. The size of the supramolecular dendrimer and of the entire unit cell increases with generation number as a result of a disproportionately large increase in the number of AB(3) repeat units relative to the number of terminal alkyl chains in a monodendron which decreases its average cone angle. The present experiments provide the first examples of monodendrons which self-assemble into spherical supramolecular dendrimers forming a thermotropic cubic LC phase.

  DOI：

  10.1021/ja963295i
• 作为产物：
  描述：

  methyl 3,4,5-tris[3',4',5'-tris(n-dodecan-1-yloxy)benzyloxy]benzoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 3,4,5-tris(3,4,5-tridodecyloxybenzyloxy)benzyl alcohol
  参考文献：
  名称：

  通过分子间氮-锌配位构建具有由叶绿素锌组装体组成的方形核的树枝状聚合物

  摘要：

  报道了由自组装的叶绿素锌衍生物组成的第一批树枝状大分子。通过吡啶固定在树枝上的附加了叶绿素的锌叶绿素锌衍生物的配位定向自组装导致树枝状分子通过吡啶环中氮原子与二氢卟吩环中锌原子之间的分子间轴向配位相互作用而在外围被树枝状分子官能化。我们通过使用1表征了环状四聚体的形成1 H NMR测量包括扩散有序光谱法（DOSY）。叶绿素锌成分中引入了四种不同类型的树突，以研究自组装对树突结构的耐受性。所有树枝状聚合物均表现出相似的稳定性，这表明树枝状分子部分不会干扰自组装，因此组装中90％以上的分子在苯中的浓度> 0.2 mM。

  DOI：

  10.1016/j.tetlet.2015.11.057

文献信息

• Cyclic Self-Assembled Structures of Chlorophyll Dyes on HOPG by the Dendron Wedge Effect
  作者：Shinobu Uemura、Sanchita Sengupta、Frank Würthner

  DOI：10.1002/anie.200902801

  日期：2009.10.5

  A molecular cake: Zinc chlorins with different dendron wedges can form linear or circular self‐assembled structures with different molecular packing. In particular, zinc chlorins with six alkyl chains in the dendron group self‐assemble into hexameric cyclic structures on HOPG (see picture). Such cyclic structures are reminiscent of (bacterio)chlorophyll organization in natural light‐harvesting systems

  分子饼：具有不同树枝状楔形的锌二氢卟酚可以形成具有不同分子堆积的线性或圆形自组装结构。特别是，树枝状基团中具有六个烷基链的二氢卟酚锌在HOPG上自组装成六聚环结构（见图）。这种环状结构让人联想到自然采光系统中的（细菌）叶绿素组织。
• Synthesis, Liquid-Crystalline Properties, and Supramolecular Nanostructures of Dendronized Poly(isocyanide)s and Their Precursors
  作者：Yanqing Tian、Kaori Kamata、Hirohisa Yoshida、Tomokazu Iyoda

  DOI：10.1002/chem.200500868

  日期：2006.1

  A series of novel dendronized pi-conjugated poly(isocyanide)s were synthesized successfully by using a Pd-Pt mu-ethynediyl dinuclear complex ([ClPtP(C2H5)3}2C[triple bond]CPtP(C2H5)3}2Cl]) as the initiator. The polymerizations of the dendronized monomers follow first-order kinetics, indicating that living polymerization takes place. The obtained polymers exhibit narrow polydispersities in the range

  使用Pd-Pt乙炔二基双核配合物（[ClPt P（C2H5）3} 2C [三键] CPt P（ ）3} 2Cl]）作为引发剂。树枝状单体的聚合遵循一级动力学，表明发生了活性聚合。所获得的聚合物在1.03-1.20的范围内显示出窄的多分散性。使用差示扫描量热法（DSC），偏振光学显微镜（POM）和广角X射线研究了聚异氰酸酯及其异氰酸酯单体和以甲酰胺基（HCONH-）为顶点的前驱体的热性能衍射（WAXD）。树突的外围和顶点基团都影响前体和单体的超分子柱和/或立方相的形成。由于分子间氢键，甲酰胺基前体形成液晶相。异氰酸酯单体缺乏这种氢键合能力，并且不显示有组织的中间相。具有单树枝状结构的所有刚性聚异氰酸酯均显示出柱状液晶相。有趣的是，聚异氰酸酯的圆柱结构可以通过透射电子显微镜（TEM）直接观察到。
• Non-covalently dendronized flavins as organocatalysts for aerobic reduction of olefins
  作者：Yasushi Imada、Yudai Kugimiya、Shotaro Iwata、Naruyoshi Komiya、Takeshi Naota

  DOI：10.1016/j.tet.2013.07.082

  日期：2013.10

  A variety of association complexes of synthetic flavin with diaminopyridine and melamine receptors are described in terms of synthesis, association properties, and catalytic activities for aerobic hydrogenation of olefins. The 1:1 association complex of lumiflavin 1 with 2,6-bis(acylamino)pyridine receptor bearing 3,4,5-trialkoxybenzyl ether dendron unit 2 acts as an efficient supramolecular organocatalyst for the aerobic reduction of styrene at ambient temperature under atmospheric air pressure. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis and Langmuir-film formation of new dendritic DTPA-derived gadolinium(III) complexes
  作者：Annabelle Bertin、Thomas Muller、Jean-Louis Gallani、Delphine Felder-Flesch

  DOI：10.1016/j.tetlet.2007.05.013

  日期：2007.7

  A series of dendritic DTPA-derived ligands and their corresponding gadolinium(III) complexes have been prepared and their spreading behaviour at the air-water interface has been investigated. The results show that these amphiphiles have the prerequisite qualities to form stable and reversible Langmuir monolayers opening the road to novel magnetic organic films. (c) 2007 Elsevier Ltd. All rights reserved.