3,5-bis(propargyloxy)benzyl chloride | 768387-52-6

• 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: 3,5-bis(propargyloxy)benzyl chloride
• 英文别名: 1-(chloromethyl)-3,5-bis(prop-2-yn-1-yloxy)benzene；3,5-Bis(propargyloxy)benzylchloride；1-(chloromethyl)-3,5-bis(prop-2-ynoxy)benzene
• CAS: 768387-52-6
• 化学式: C₁₃H₁₁ClO₂
• 分子量: 234.682
• InChiKey: GKVVWLHPDYIHQD-UHFFFAOYSA-N

物化性质

• 沸点：
  370.4±42.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-bis(propargyloxy)benzyl chloride 在 sodium azide 、 溴化三(三苯基磷)铜 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 24.08h， 生成 4-[[3-(Azidomethyl)-5-[(1-benzyltriazol-4-yl)methoxy]phenoxy]methyl]-1-benzyltriazole
  参考文献：
  名称：

  通过铜（i）催化的叠氮化物和炔烃的点击化学合成三唑树枝状聚合物的效率和保真度。

  摘要：

  DOI：

  10.1002/anie.200454078
• 作为产物：
  描述：

  3,5-二羟基苯甲酸 在 lithium aluminium tetrahydride 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 28.5h， 生成 3,5-bis(propargyloxy)benzyl chloride
  参考文献：
  名称：

  Selective Upper Rim Functionalization and Lower Rim Bridge Building with Calix[4]arenes and Calix[6]arenes¹

  摘要：

  Selective upper rim functionalization of calix[6]arenes has been achieved by selective lower rim benzoylation at the 1,2,4,5 positions followed by AlCl3-induced removal of the tert-butyl groups of the unesterified aryl residues and introduction of various functionalities into the vacated para positions, including bromo (5), dialkylamino, (7-11) cyanomethyl (12), and (propargyloxy)methyl (13) groups. Lower rim bridge building has been achieved via oxidative coupling reactions between the aryne moieties of calix[4]arenes and calix[6]arenes in which O-benzyl groups carry one (from 23 and 24) or two (from 25) propargyloxy residues. In the calix[4]arene series both a single-spanned (32) and a double-spanned (33) double-cavity calixarene were obtained. In the calix[6]arene series only a single-spanned double cavity calixarene (36) could be characterized.

  DOI：

  10.1021/jo952054a

文献信息

• Synthesis, optical properties, and antioxidant and anticancer activity of benzoheterazole dendrimers with triazole bridging unit
  作者：Kannan Rajavelu、Mamangam Subaraja、Perumal Rajakumar

  DOI：10.1039/c7nj04060a

  日期：——

  scavenging methods. Higher generation dendrimers exhibit superior antioxidant activity than the lower generation dendrimers due to the presence of a higher number of 1,2,3-triazole and benzophenone units. The therapeutic efficacy of the benzoheterazole dendrimers in inhibiting the growth of the A549 cancer cell increases as the dendritic generation increases. Our study shows that the inhibition of cell

  通过点击化学，通过收敛方法已经合成了具有双酚/二苯甲酮核心单元的三唑桥连的苯并杂唑树枝状大分子。研究了苯并杂唑树枝状大分子的光学性质及其在树枝状环境影响下的调制。所有合成的苯并杂唑树枝状聚合物均显示出与标准品相当的抗氧化性能，即：没食子酸和抗坏血酸，通过DPPH和ABTS自由基清除方法测试时。由于存在较高数量的1,2,3-三唑和二苯甲酮单元，因此较高代的树状聚合物比较低代的树状聚合物表现出优异的抗氧化活性。随着树突生成的增加，苯并杂唑树状聚合物抑制A549癌细胞生长的治疗功效也增加。我们的研究表明，抑制细胞增殖与剂量和时间有关。MTT分析，细胞活力，细胞计数和克隆形成分析表明，如活性氧和线粒体膜电位研究所揭示的，苯并杂唑树状聚合物可抑制癌细胞的生长。
• Synthesis and DSSC application of novel dendrimers with benzothiazole and triazole units
  作者：Perumal Rajakumar、Venkatesan Kalpana、Shanmugam Ganesan、Pichai Maruthamuthu

  DOI：10.1016/j.tetlet.2011.08.126

  日期：2011.11

  Synthesis of novel dendrimers with benzothiazole as surface group and triazole as branching unit is achieved through click chemistry. The presence of more number of benzothiazole and triazole units increases the molar absorption coefficient and alters the fluorescence as well as electrochemical behaviors in the dendrimers. Dye-sensitized solar cell (DSSC) studies reveal that dendrimers with more number

  通过点击化学合成了以苯并噻唑为表面基团和三唑为支化单元的新型树枝状大分子。大量苯并噻唑和三唑单元的存在增加了摩尔吸收系数，并改变了树枝状聚合物中的荧光以及电化学行为。染料敏化太阳能电池（DSSC）研究表明，苯并噻唑和三唑基团数量较多的树枝状聚合物比苯并噻唑和三唑基团数量较少的树枝状聚合物表现出更好的电流产生能力。树枝状聚合物2b显示出7.1％的最大电流转换效率（η）。
• Synthesis and optical and electrochemical properties of glucose-cored ferrocenyl dendrimers
  作者：Ayyavoo Kannan、Ramasamy Anandhan、Perumal Rajakumar

  DOI：10.1080/00397911.2016.1245752

  日期：2017.3.19

  cycloaddition (CuAAC) of azidoferrocenyl derivatives with glucose pentaacetylide. Higher generation ferrocenyl glycoconjugates form the stable ferrocenium cation and exhibit increased light harvesting property as revealed from cyclic voltammogram studies and ultraviolet–visible spectrum respectively due to the presence of more ferrocenyl and triazolyl units than the lower generation dendrimer. GRAPHICAL

  摘要 通过区域特异性铜（I）催化叠氮二茂铁衍生物与五乙炔葡萄糖的叠氮-炔环加成反应（CuAAC），合成了基于三唑的二茂铁基糖缀合物 1、2 和 3。循环伏安图研究和紫外-可见光谱分别显示，由于存在比低代树枝状聚合物更多的二茂铁基和三唑基单元，更高代的二茂铁基糖缀合物形成稳定的二茂铁阳离子并表现出增强的光捕获特性。图形概要
• Click Chemistry Inspired Synthesis of Glycoporphyrin Dendrimers
  作者：Divya Kushwaha、Vinod K. Tiwari

  DOI：10.1021/jo4012392

  日期：2013.8.16

  A series of porphyrin-cored glycodendrimers containing 8, 12, 16, and 24 β-d-glucopyranose units at the periphery, have been synthesized by convergent methodology using click chemistry. The structure of developed dendrimers is established by 1H and 13C NMR, IR, MALDI-TOF MS, and SEC analysis. Absorption–emission behavior of dendrimers and its modulation under the influence of the dendritic environment

  通过点击法，通过收敛方法合成了一系列在外围含有8、12、16和24个β- d-吡喃葡萄糖的卟啉核心的糖树状聚合物。通过1 H和13 C NMR，IR，MALDI-TOF MS和SEC分析确定发达的树状聚合物的结构。还研究了树枝状聚合物的吸收-发射行为及其在树枝状环境影响下的调节作用。
• Synthesis, photophysical, electrochemical, and DSSC application of novel donor–acceptor triazole bridged dendrimers with a triphenylamine core and benzoheterazole as a surface unit
  作者：Kannan Rajavelu、Perumal Rajakumar、Mandal Sudip、Ramanujam Kothandaraman

  DOI：10.1039/c6nj02126c

  日期：——

  Triazole bridged novel donor–acceptor dendrimers with triphenylamine as the core and benzoheterazole as the surface unit have been synthesized by click chemistry via a convergent approach. All the dendrimers exhibited excellent optical and electrochemical properties, as supported by DFT calculations. Lower generation dendrimers exhibit better current-generating capacity and also show better power conversion

  三唑桥联的新型供体-受体树枝状大分子，以三苯胺为核心，苯并杂唑为表面单元，是通过点击化学通过收敛方法合成的。所有的树枝状聚合物均表现出优异的光学和电化学性能，这得到DFT计算的支持。当用作染料敏化太阳能电池的添加剂时，低代树状聚合物表现出更好的电流产生能力，并且还表现出比高代树状聚合物更好的功率转换效率。