1,3,5-Tris-(4-brombutoxy)benzol | 63604-99-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,3,5-Tris-(4-brombutoxy)benzol
• 英文别名: 1,3,5-Tris(4-bromobutoxy)benzene
• CAS: 63604-99-9
• 化学式: C₁₈H₂₇Br₃O₃
• 分子量: 531.123
• InChiKey: VOUYMSOGBRHIJF-UHFFFAOYSA-N

物化性质

• 熔点：
  43-44 °C(Solv: dichloromethane (75-09-2))
• 沸点：
  557.1±50.0 °C(Predicted)
• 密度：
  1.519±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  24
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3,5-Tris-(4-brombutoxy)benzol 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 (R,R,R)-C6H3(O(CH2)4C2HN3CH2OCH(CH3)C5H4N)3
  参考文献：
  名称：

  Highly Stable Chiral (A)₆–B Supramolecular Copolymers: A Multivalency-Based Self-Assembly Process

  摘要：

  A novel type of chiral layered supramolecular copolymer with high molecular weight has been assembled from a hydrogen bonded C-6-symmetric zinc porphyrin hexamer and chiral C-3-symmetric pyridine hexadentate linkers driven by multivalent zinc porphyrin-pyridine coordination. UV-vis, circular dichroism, and static light scattering experiments revealed that the formation of the layered supramolecular copolymers is at first dynamically controlled and then becomes thermodynamically controlled.

  DOI：

  10.1021/ja205059z
• 作为产物：
  描述：

  1,4-二溴丁烷 、 间苯三酚 在 potassium carbonate 作用下， 生成 1,3,5-Tris-(4-brombutoxy)benzol
  参考文献：
  名称：

  1,6,13,18,25,30-六氧杂[6.6.6]（1,3,5）环烷。尝试合成[4]密码子

  摘要：

  六恶[5.5.5]（1,3,5）环烷（12）是由间苯三酚和1,4-二溴丁烷通过逐步方法合成的。已经证明所有尝试对六氧杂环[6.6.6]（1,3,5）环烷（12）中的两个芳环进行催化加氢以生成所需的[4] cryptand（14）的尝试均未成功。

  DOI：

  10.1039/p19770000785

文献信息

• A photocontrollable supramolecular hyperbranched polymer based on host-guest recognition in aqueous solution
  作者：Lei Zou、Zhiyi Yuan、Dongdong Chang、Xiang Ma

  DOI：10.1016/j.dyepig.2017.04.027

  日期：2017.8

  A novel supramolecular hyperbranched polymer had been fabricated conveniently through host-guest recognition based on Cucurbit[8]uril in aqueous solution. The three branched monomer contained an azobenzene unit and a viologen moiety on each of its branch. The polymerization of the supramolecular polymer in water could be controlled by tuning the isomer ratio of azobenzene groups of the guest monomers

  通过基于Cucurbit [8] uril的客体识别，方便地制备了一种新型的超分子超支化聚合物。三个支链单体在其每个支链上均包含偶氮苯单元和紫精部分。超分子聚合物在水中的聚合可通过在光竞争照射下调节客体单体的偶氮苯基的异构体比率来控制。另外，可以通过改变主体和客体单体之间的摩尔比来调节结构的严格性。通过在光滑平面上干燥超分子超支化聚合物溶液的溶剂来构建平面超分子网络。该研究提供了一种进行双反应超分子聚合的有前途的方法。
• Supramolecular Polymers Based on Efficient Pillar[5]arene-Neutral Guest Motifs
  作者：Chunju Li、Kang Han、Jian Li、Yanyan Zhang、Wei Chen、Yihua Yu、Xueshun Jia

  DOI：10.1002/chem.201301022

  日期：2013.9.2

  Neutral and efficient: A neutral guest with a cyano site and a triazole site, which can be easily prepared and modified, is demonstrated to strongly bind with pillar[5]arene (see figure). Based on this new recognition motif, two neutral supramolecular polymers in organic media, which are currently unfeasible by means of host–guest interactions of crown ethers and calixarenes, were fabricated. One is

  中性和高效：具有氰基位点和三唑位点的中性客体，可以很容易地制备和修饰，并被证明与柱[5]芳烃牢固结合（见图）。基于这个新的识别基序，在有机介质中制造了两种中性的超分子聚合物，目前尚无法通过冠醚和杯芳烃的客体相互作用实现。一个是AA / BB型，另一个是A 2 / B 3型。
• New Ditopic and Tripodal 1,2,4-Triazole- and Tetrazole-Based Ligands for Coordination Chemistry
  作者：Yann Garcia、Yves Boland、Pascale Hertsens、Jacqueline Marchand-Brynaert

  DOI：10.1055/s-2006-926439

  日期：2006.5

  amine precursors. The first family consisted of ditopic ligands containing both 1-R-tetrazole and 4-R-1,2,4-triazole moieties linked by an alkyl spacer, white the second consists of branched ligands with three azole cycles linked to a benzene core through ether bonds. Both classes are suitable for building multidimensional polynuclear coordination assemblies and for the observation of thermal spin state

  报道了两类新的基于唑类的多面体配体的实际合成。前体胺的合成是通过用叠氮化物取代离去基团，然后用三苯膦和水还原来实现的。另一种有效的方法是使用 Mitsunobu 与邻苯二甲酰亚胺偶联，从而将伯醇转化为伯胺。通过这些胺前体的环化得到三唑和四唑。第一个家族由包含通过烷基间隔连接的 1-R-四唑和 4-R-1,2,4-三唑部分的双位配体组成，第二个家族由具有三个唑环的支链配体组成醚键。
• Crystalline Nanoparticles of Water‐Soluble Covalent Basket Cages (CBCs) for Encapsulation of Anticancer Drugs
  作者：Vageesha W. Liyana Gunawardana、Carson Ward、Han Wang、Joseph H. Holbrook、Emily R. Sekera、Honggang Cui、Amanda B. Hummon、Jovica D. Badjić

  DOI：10.1002/anie.202306722

  日期：2023.8.14

  We herein describe the preparation, assembly, recognition characteristics, and biocompatibility of novel covalent basket cage CBC‐11, composed of four molecular baskets linked to four trivalent aromatic amines through amide groups. The cage is tetrahedral in shape and similar in size to small proteins (M_w=8637 g/mol) with a spacious nonpolar interior for accommodating multiple guests. While 24 carboxylates at the outer surface of CBC‐11 render it soluble in aqueous phosphate buffer (PBS) at pH=7.0, the amphiphilic nature prompts its assembly into nanoparticles (d=250 nm, DLS). Cryo‐TEM examination of nanoparticles revealed their crystalline nature with wafer‐like shapes and hexagonally arranged cages. Nanoparticulate CBC‐11 traps anticancer drugs irinotecan and doxorubicin, with each cage binding up to four drug molecules in a non‐cooperative manner. The inclusion complexation resulted in nanoparticles growing in size and precipitating. In media containing mammalian cells (HCT 116, human colon carcinoma), the IC₅₀ value of CBC‐11 was above 100 μM. While this work presents the first example of a large covalent organic cage operating in water at the physiological pH and forming crystalline nanoparticles, it also demonstrates its biocompatibility and potential to act as a polyvalent binder of drugs for their sequestration or delivery.

  摘要 我们在此介绍新型共价篮笼 CBC-11 的制备、组装、识别特性和生物相容性，它由四个分子篮组成，通过酰胺基团与四个三价芳香胺相连。这种笼子呈四面体形状，大小与小型蛋白质相似（Mw=8637 g/mol），具有宽敞的非极性内部空间，可容纳多种客体。虽然 CBC-11 外表面的 24 个羧基使其可溶于 pH=7.0 的磷酸盐缓冲液（PBS）水溶液中，但两亲性促使其组装成纳米颗粒（d=250 nm，DLS）。对纳米颗粒进行的冷冻-TEM 检查显示，它们具有晶圆状和六角形笼状排列的结晶性质。纳米微粒 CBC-11 可捕获抗癌药物伊立替康和多柔比星，每个笼子以非合作方式结合多达四个药物分子。包涵复合物导致纳米颗粒增大并沉淀。在含有哺乳动物细胞（HCT 116，人类结肠癌）的培养基中，CBC-11 的 IC50 值超过 100 μM。这项研究首次展示了一种大型共价有机笼在生理 pH 值的水中运行并形成结晶纳米颗粒的实例，同时也证明了它的生物相容性以及作为多价药物粘合剂用于药物封存或递送的潜力。
• Triisocyano-based trinuclear gold(I) complexes with aggregation-induced emission (AIE) and mechanochromic luminescence characteristics
  作者：Zhao Chen、Peng-Shou Huang、Zheng Li、Jun Yin、Guang-Ao Yu、Sheng Hua Liu

  DOI：10.1016/j.ica.2015.04.016

  日期：2015.6

  Three novel trinuclear gold(I) complexes have been designed and synthesized. These gold(I) complexes exhibit aggregation-induced emission characteristics. Furthermore, the photoluminescence properties of these luminogens show off-on green fluorescence in response to mechanical grinding. The changing of weak multiple intermolecular C-H center dot center dot center dot F or pi-pi interactions, or the formation of aurophilic interactions are possibly responsible for their mechanochromism phenomena. (C) 2015 Elsevier B.V. All rights reserved.