3-(1,1,1-trimethylsilyl)-2-propynyl 2-bromo-2-methylpropanoate | 847043-15-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-(1,1,1-trimethylsilyl)-2-propynyl 2-bromo-2-methylpropanoate
• 英文别名: 3-(trimethylsilyl)prop-2-yn-1-yl 2-bromo-2-methylpropanoate；3-trimethylsilyl-2 propynyl-2-bromo-2-methylpropanoate；3-(trimethylsilyl)propargyl 2-bromoisobutyrate；TMSCCBr；3-(Trimethylsilyl)prop-2-YN-1-YL 2-bromo-2-methylpropanoate；3-trimethylsilylprop-2-ynyl 2-bromo-2-methylpropanoate
• CAS: 847043-15-6
• 化学式: C₁₀H₁₇BrO₂Si
• 分子量: 277.233
• InChiKey: AVJHIDARCIGTOR-UHFFFAOYSA-N

物化性质

• 沸点：
  257.5±20.0 °C(Predicted)
• 密度：
  1.208±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-溴-2-甲基丙酰溴 、 三甲硅基丙炔醇 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以93%的产率得到3-(1,1,1-trimethylsilyl)-2-propynyl 2-bromo-2-methylpropanoate
  参考文献：
  名称：

  Modular synthesis of block copolymers via cycloaddition of terminal azide and alkyne functionalized polymers

  摘要：

  通过原子转移自由基聚合反应（ATRP）制备了含有叠氮和炔烃官能团的聚合物构筑基块，并通过 1,3-二极环加成反应模块化地合成了嵌段共聚物。

  DOI：

  10.1039/b412930j

文献信息

• DENDRITIC MOLECULES
  申请人：Monteiro Michael John

  公开号：US20120059173A1

  公开（公告）日：2012-03-08

  The invention relates to novel dendritic molecules and methods of making them. The dendritic molecules comprise arms, each of which arms is a polymer. The dendritic molecules can be synthesised by way of a reasonably small number of versatile and reliable step-wise reactions, especially click chemistry reactions. Chemical and structural heterogeneity is possible in the dendritic molecule. The invention also provides for surface and interior functionalisation of the molecule.

  该发明涉及新型树状分子及其制备方法。这些树状分子包括臂，每个臂都是一种聚合物。这些树状分子可以通过相对少量的多功能和可靠的逐步反应合成，特别是点击化学反应。树状分子中可能存在化学和结构上的异质性。该发明还提供了对分子的表面和内部功能化。
• Synthesis of poly(2-hydroxyethyl methacrylate) end-capped with asymmetric functional groups via atom transfer radical polymerization
  作者：Chengmin Hou、Shudong Lin、Feng Liu、Jiwen Hu、Ganwei Zhang、Guojun Liu、Yuanyuan Tu、Hailiang Zou、Hongsheng Luo

  DOI：10.1039/c3nj01398g

  日期：——

  (CH3)3Si–CC–PHEMA–Cl as a macroinitiator. The methoxyl polyethylene glycol-block-poly(2-hydroxyethyl methacrylate) (MPEG-b-PHEMA) diblock copolymer was prepared by click reaction between MPEG-N3 and HCC–PHEMA–Cl. These two reactions demonstrated the reactivity of the asymmetric functional groups end-capping the PHEMA, and further provided modular examples for the synthesis of a novel well-defined (co)polymer with

  在甲醇和2-丁酮的溶剂混合物中，使用CuCl / CuCl 2 / 2,2'-联吡啶作为催化剂，通过HEMA的ATRP合成了带有活泼氯和炔基封端的聚甲基丙烯酸2-羟乙酯。根据聚合动力学，聚合度（DP）和摩尔质量分散度（Đ），研究了引发剂，溶剂，温度和初始单体与引发剂比例等参数对聚合的影响。）所得的PHEMA聚合物。使用2-溴异丁炔丙基炔丙基（PBiB）作为引发剂的HEMA的ATRP控制不佳，但是使用3-（三甲基甲硅烷基）炔丙基2-溴异丁酸酯（TMSPBiB）和3-（三异丙基甲硅烷基）炔丙基2-溴异丁酸酯（TiPSPBiB）的HEMA的ATRP效果良好。 -受控。此外，使用TMSPBiB引发剂的HEMA ATRP的表观传播速率常数高于使用TiPSPBiB引发剂的表观传播速率常数。甲醇-2-丁酮在不同组成下的混合溶剂极大地影响了聚合反应的可控制性。在适当的条件下获得了DP值为1000和Đ为1.
• Prop-2-yn-1-yl 2-Bromo-2-methylpropanoate: Identification and Suppression of Side Reactions of a Commonly Used Terminal Alkyne-Functional ATRP Initiator
  作者：William K. Storms-Miller、Coleen Pugh

  DOI：10.1021/acs.macromol.5b00652

  日期：2015.6.23

  The atom transfer radical polymerization (ATRP) of styrene was investigated using the popular alkyne-functional initiator prop-2-yn-1-yl 2-bromo-2-methylpropanoate (PBiB). The polymerization kinetics and evolution of molecular weight as a function of monomer conversion were systematically studied with PBiB and similar initiators with protecting groups at the reactive propargylic and terminal acetylenic

  使用流行的炔烃官能引发剂2-溴-2-甲基丙酸丙-2-炔-1-基丙酯（PBiB）研究了苯乙烯的原子转移自由基聚合（ATRP）。用PBiB和类似的在反应性炔丙基和炔基末端带有保护基的引发剂，系统地研究了聚合动力学和分子量随单体转化率的变化。将这些研究与使用非功能性引发剂2-溴异丁酸乙酯的对照研究进行了比较。如模型反应的NMR分析所证实的，末端炔烃在ATRP条件下会经历氧化炔烃-炔烃偶联反应，从而产生具有双峰分子量分布的聚合物。
• Synthesis of cyclic polyelectrolyte via direct copper(I)-catalyzed click cyclization
  作者：Fenggui Chen、Guangming Liu、Guangzhao Zhang

  DOI：10.1002/pola.25869

  日期：2012.3.1

  Well‐defined cyclic poly(acrylic acid) (PAA) has been successfully prepared based on the direct click cyclization. The linear poly(tert‐butyl acrylate) (PtBA) with azide and TMS‐protected alkyne group forms cyclic chain directly by the copper(I)‐catalyzed click cyclization without any deprotection steps. Cyclic PAA is synthesized by the hydrolysis of cyclic PtBA. The present synthetic strategy provides

  在直接点击环化的基础上，已经成功制备了定义明确的环状聚丙烯酸（PAA）。带有叠氮化物和TMS保护的炔基的线性聚（丙烯酸叔丁酯）（P t BA）通过铜（I）催化的点击环化直接形成环状链，而无需任何脱保护步骤。环状PAA是通过环状P t BA的水解而合成的。本合成策略提供了一种合成环状聚电解质的简单有效的方法，并且可以应用于其他聚合物体系。
• Grafting Efficiency of Synthetic Polymers onto Biomaterials: A Comparative Study of Grafting-<i>from</i> versus Grafting-<i>to</i>
  作者：Susanne Hansson、Vanessa Trouillet、Thomas Tischer、Anja S. Goldmann、Anna Carlmark、Christopher Barner-Kowollik、Eva Malmström

  DOI：10.1021/bm3013132

  日期：2013.1.14

  In the present study, the two grafting techniques grafting-from - by activators regenerated by electron transfer atom transfer radical polymerization (ARGET ATRP) - and grafting-to - by copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) - were systematically compared, employing cellulose as a substrate. In order to obtain a meaningful comparison, it is crucial that the graft lengths of the polymers that are grafted from and to the substrates are essentially identical. Herein, this was achieved by utilizing the free polymer formed in parallel to the grafting from reaction as the polymer for the grafting-to reaction. Four graft lengths were investigated, and the molar masses of the four free polymers (21 <= M-n <= 100 kDa; 1.07 <= D-M <= 1.26), i.e. the polymers subsequently employed in the grafting to reaction, were shown to be in the same range as the molar masses of the polymers grafted from the surface (23 <= M-n <= 87 kDa; 1.08 <= D-M <= 1.31). The molecular weights of the chains grafted from the surface were established after cleavage from the cellulose substrates via size exclusion chromatography (SEC). High-resolution Fourier transform infrared microscopy (FT-IRM) was employed as an efficient tool to study the spatial distribution of the polymer content on the grafted substrates. In addition, the functionalizeid substrates were analyzed by X-ray photoelectron spectroscopy (XPS), contact angle (CA) measurements, and field-emission scanning electron microscopy (FE-SEM). For cellulose substrates modified via the grafting-from approach, the content of polymer on the surfaces increased with increasing graft length, confirming the possibility to tailor not only the length of the polymer grafts but also the polymeric content on the surface. In comparison, for the grafting to reaction, the grafted content could not be controlled by varying the length of the preformed polymer: the polymer content was essentially the same for the four graft lengths. Consequently, the obtained results, when employing cellulose as a substrate and under these conditions, suggest that the grafting-from approach is superior to the grafting-to technique with respect to controlling the distribution of the polymeric content on the surface.