1,3,5-三[4-(氯甲基)苯基]苯 | 66449-09-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,3,5-三[4-(氯甲基)苯基]苯
• 英文名称: 1,3,5-tris(p-chlorophenyl)benzene
• 英文别名: 1,3,5-tris(p-chloromethylphenyl)benzene；tris-1,3,5-(4'-chloromethyl)benzene；1,3,5-Tris[4-(chloromethyl)phenyl]benzene
• CAS: 66449-09-0
• 化学式: C₂₇H₂₁Cl₃
• 分子量: 451.823
• InChiKey: AMGIKSOVIQLLIM-UHFFFAOYSA-N

物化性质

• 熔点：
  162-163 °C
• 沸点：
  599.2±50.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 危险类别：
  8
• 危险性防范说明：
  P264,P270,P271,P280,P303+P361+P353,P304+P340,P305+P351+P338,P310,P330,P331,P363,P403+P233,P501
• 危险品运输编号：
  3261
• 危险性描述：
  H302,H314
• 包装等级：
  II

反应信息

• 作为反应物：
  描述：

  1,3,5-三[4-(氯甲基)苯基]苯 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以86%的产率得到1,3,5-tris(p-azidomethylphenyl)benzene
  参考文献：
  名称：

  使用顺序Cu（I）催化的叠氮化物-炔烃环加成反应的一锅合成结构不对称轮烷。

  摘要：

  提出了一锅顺序Cu（I）催化的叠氮化物-炔烃环加成（CuAAC）策略，用于从简单的起始原料以高收率合成结构不对称的基于环双（百草枯-对苯撑）的轮烷。该方法包括逐步进行多个CuAAC反应以终止假轮烷，其顺序通过末端炔基的甲硅烷基保护和Ag（I）催化的脱保护作用来控制。两亲性支链[4]轮烷的合成突出了该方法。该方法提高了访问越来越复杂的机械互锁化合物以在设备中用作复杂和功能性分子机械的能力。

  DOI：

  10.1002/chem.200800067
• 作为产物：
  描述：

  4-[3,5-二(4-甲酰基苯基)苯基]苯甲醛 在 sodium tetrahydroborate 、 N-氯代丁二酰亚胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 1,3,5-三[4-(氯甲基)苯基]苯
  参考文献：
  名称：

  Can Multivalency Be Expressed Kinetically? The Answer Is Yes

  摘要：

  Inspired by the concept of multivalency and in pursuit of ever more intricate artificial molecular machines, we investigated the strict self-assembly of a triply threaded two-component superbundle, starting from a tritopic receptor in which three benzo[24]crown-8 macrorings are fused onto a triphenylene core and a trifurcated trication wherein three bipyridinium units are linked 1,3,5 to a central benzenoid core. The result of the investigation was quite unexpected and surprising. It transpired that the rapid formation of a doubly threaded two-component complex was followed by an extremely slow conversion (a week at 253 K in CD3COCD3 to reach equilibrium) of this kinetically controlled product into a thermodynamically controlled one, namely a triply threaded two-component superbundle. This intriguing observation begs the question: are there instances in nature where multivalency is expressed as a kinetically controlled process, prior to an equilibrium state being reached, and if so, what are the biological implications, if any?

  DOI：

  10.1021/ja0395285

文献信息

• 1，3，5-三(对-叠氮甲基)三苯基苯及其制备方法
  申请人：湖北航天化学技术研究所

  公开号：CN105566154A

  公开（公告）日：2016-05-11

  一种1，3，5-三(对-叠氮甲基)三苯基苯及其制备方法，包括以下工序将卤代芳烃溶于反应溶剂，反应时间3~15小时，反应完全后降至室温，加入去离子水停止反应，用二氯甲烷萃取三次，减压蒸馏除去二氯甲烷得棕褐色粘稠状产品。本发明的含三个叠氮基团的三苯基苯化合物1，3，5-三(对-叠氮甲基)三苯基苯室温下为棕褐色粘稠状化合物，摩擦感度为0，撞击感度I50为27焦耳。本发明的合成步骤简单，条件温和，不需要特别的合成装置；1，3，5-三(对-叠氮甲基)三苯基苯的熔点低，溶于丙酮、乙醇、N,N-二甲基甲酰胺等多种溶剂，在低温固化高温使用的超支化聚三唑弹性体制备方面有着潜在的应用前景。
• A One-Pot Synthesis of Constitutionally Unsymmetrical Rotaxanes Using Sequential CuI-Catalyzed Azide–Alkyne Cycloadditions
  作者：Jason M. Spruell、William R. Dichtel、James R. Heath、J. Fraser Stoddart

  DOI：10.1002/chem.200800067

  日期：2008.5.9

  A one-pot sequential Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) strategy is presented for the synthesis of constitutionally unsymmetrical cyclobis(paraquat-p-phenylene)-based rotaxanes in good yields from simple starting materials. The methodology consists of performing multiple CuAAC reactions to stopper a pseudorotaxane in a stepwise manner, the order of which is controlled through silyl-protection

  提出了一锅顺序Cu（I）催化的叠氮化物-炔烃环加成（CuAAC）策略，用于从简单的起始原料以高收率合成结构不对称的基于环双（百草枯-对苯撑）的轮烷。该方法包括逐步进行多个CuAAC反应以终止假轮烷，其顺序通过末端炔基的甲硅烷基保护和Ag（I）催化的脱保护作用来控制。两亲性支链[4]轮烷的合成突出了该方法。该方法提高了访问越来越复杂的机械互锁化合物以在设备中用作复杂和功能性分子机械的能力。
• Can Multivalency Be Expressed Kinetically? The Answer Is Yes
  作者：Jovica D. Badjić、Stuart J. Cantrill、J. Fraser Stoddart

  DOI：10.1021/ja0395285

  日期：2004.3.3

  Inspired by the concept of multivalency and in pursuit of ever more intricate artificial molecular machines, we investigated the strict self-assembly of a triply threaded two-component superbundle, starting from a tritopic receptor in which three benzo[24]crown-8 macrorings are fused onto a triphenylene core and a trifurcated trication wherein three bipyridinium units are linked 1,3,5 to a central benzenoid core. The result of the investigation was quite unexpected and surprising. It transpired that the rapid formation of a doubly threaded two-component complex was followed by an extremely slow conversion (a week at 253 K in CD3COCD3 to reach equilibrium) of this kinetically controlled product into a thermodynamically controlled one, namely a triply threaded two-component superbundle. This intriguing observation begs the question: are there instances in nature where multivalency is expressed as a kinetically controlled process, prior to an equilibrium state being reached, and if so, what are the biological implications, if any?