1-(prop-2-yn-1-yloxy)-2,2-bis((prop-2-yn-1-yloxy)methyl)butane | 353520-68-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(prop-2-yn-1-yloxy)-2,2-bis((prop-2-yn-1-yloxy)methyl)butane
• 英文别名: 1-Prop-2-ynoxy-2,2-bis(prop-2-ynoxymethyl)butane；1-prop-2-ynoxy-2,2-bis(prop-2-ynoxymethyl)butane
• CAS: 353520-68-0
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: MAIRLRSIWYVERD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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-(prop-2-yn-1-yloxy)-2,2-bis((prop-2-yn-1-yloxy)methyl)butane 、 在 五甲基二乙烯三胺 、 copper(I) bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以72%的产率得到
  参考文献：
  名称：

  “点击”合成每个支链单元均含有金属结合部分的亲水性树枝状和树枝状大分子

  摘要：

  通过专门设计的Cu（I）催化的炔-叠氮化物环加成反应（CuAAC），创建了由三（乙二醇）（TrEG）和双（羟甲基）丙酸（bis-MPA）组成的新的水溶性三唑树枝状聚合物家族。互补的构建基块。CuAAC将三代之前的树枝状大分子合成为三官能核，其收率范围从第一代的72％，第二代的67％和第三代树状聚合物的64％。每个bis-MPA分支位置的两个三唑环可作为某些VIIIA组元素的有效螯合口袋。作为原理的证明，对这些亲水性树突状配体的[PdCl 2（PhCN）2 ]配位化学进行了研究[ 1]。1 H NMR，动态光散射，透射电子显微镜和DFT计算。结果表明络合在5分钟内完成。新型亲水性树枝状Pd络合物能够在100°C，60°C甚至在50°C的3 h内催化Suzuki–Miyaura在水中的偶合反应，并且具有实际的定量转化率。

  DOI：

  10.1021/ma500126f
• 作为产物：
  描述：

  三羟甲基丙烷 、 3-溴丙炔 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 6.0h， 以79%的产率得到1-(prop-2-yn-1-yloxy)-2,2-bis((prop-2-yn-1-yloxy)methyl)butane
  参考文献：
  名称：

  “点击”合成每个支链单元均含有金属结合部分的亲水性树枝状和树枝状大分子

  摘要：

  通过专门设计的Cu（I）催化的炔-叠氮化物环加成反应（CuAAC），创建了由三（乙二醇）（TrEG）和双（羟甲基）丙酸（bis-MPA）组成的新的水溶性三唑树枝状聚合物家族。互补的构建基块。CuAAC将三代之前的树枝状大分子合成为三官能核，其收率范围从第一代的72％，第二代的67％和第三代树状聚合物的64％。每个bis-MPA分支位置的两个三唑环可作为某些VIIIA组元素的有效螯合口袋。作为原理的证明，对这些亲水性树突状配体的[PdCl 2（PhCN）2 ]配位化学进行了研究[ 1]。1 H NMR，动态光散射，透射电子显微镜和DFT计算。结果表明络合在5分钟内完成。新型亲水性树枝状Pd络合物能够在100°C，60°C甚至在50°C的3 h内催化Suzuki–Miyaura在水中的偶合反应，并且具有实际的定量转化率。

  DOI：

  10.1021/ma500126f

文献信息

• Reactions of Unsaturated Azides; Part 22: The Alkyne Azide Click Chemistry as a Synthetic Tool for the Generation of Cage-Like Triazole Compounds
  作者：Klaus Banert、Jens Wutke、Tobias Rüffer、Heinrich Lang

  DOI：10.1055/s-2008-1078602

  日期：2008.8

  applicability of the copper(I)-catalyzed click reaction of terminal trialkynes with triazides to the synthesis of cage-like triazole compounds was determined. A number of starting materials were prepared and several monotriazoles as well as macrocyclic bistriazoles were obtained from the triazide trialkyne reaction. Finally, a tristriazole macrobicyclic compound was synthesized from the previously formed

  确定了铜 (I) 催化的末端三炔烃与三叠氮化物的点击反应在合成笼状三唑化合物中的适用性。制备了许多起始材料，并从三叠氮化物三炔反应中获得了几种单三唑以及大环双三唑。最后，由先前形成的三唑前体合成了三唑大双环化合物。
• Photopolymerization Reactions Using the Photoinitiated Copper (I)-Catalyzed Azide-Alkyne Cycloaddition (CuAAC) Reaction
  作者：Tao Gong、Brian J. Adzima、Noah H. Baker、Christopher N. Bowman

  DOI：10.1002/adma.201203815

  日期：2013.4.11

  The first bulk photopolymerization of multifunctional alkyne and azide monomers using the CuAAC reaction is successfully carried out from low molecular weight, nonviscous monomer resins. Compared to other traditional step‐growth bulk photopolymerization, this approach readily provides crosslinked, high glass transition temperature polymers that incorporate triazole linkages throughout the polymer structure

  使用CuAAC反应的多官能炔烃和叠氮化物单体的第一次本体光聚合成功地由低分子量，非粘性单体树脂进行。与其他传统的逐步增长的本体光聚合反应相比，该方法可轻松提供交联的，高玻璃化温度的聚合物，该聚合物在整个聚合物结构中结合了三唑键，并具有良好的时间控制性。
• PROCESSES FOR PREPARING CURED FILMS, THE RESULTING FILMS, AND PLASMA-INITIATED POLYMERIZABLE COMPOSITIONS
  申请人：FUJIFILM Corporation

  公开号：US20140170405A1

  公开（公告）日：2014-06-19

  Provided are novel plasma-assisted processes for preparing cured films having excellent heat resistance and moisture resistance. A process for preparing a cured film, comprising at least: applying a composition containing (A) at least one conductive polymer precursor on a substrate to form a coating layer, and irradiating the coating layer with a plasma to polymerize the conductive polymer precursor (A).

  提供了一种新型等离子体辅助制备固化膜的工艺，该固化膜具有优异的耐热性和耐潮性。一种制备固化膜的工艺，包括至少以下步骤：在基板上涂布含有（A）至少一种导电聚合物前体的组合物以形成涂层层，然后用等离子体照射涂层层以聚合导电聚合物前体（A）。
• Development of a triazole-cure resin system for composites: Evaluation of alkyne curatives
  作者：Irene E. Gorman、Rodney L. Willer、Lisa K. Kemp、Robson F. Storey

  DOI：10.1016/j.polymer.2012.04.002

  日期：2012.6

  We are developing a resin system that cures via triazole ring formation (cycloaddition reaction of azides with terminal alkynes) instead of the traditional oxirane/amine reaction. The high exothermicity of the azido/alkyne reaction is expected to yield higher extents of reaction under ambient-cure conditions, making the resin system potentially suitable for "out-of-autoclave" curing processes. The difunctional azide-terminated resin, di(3-azido-2-hydroxypropyl) ether of bisphenol-A, was selected as the baseline diazide. A number of alkyne crosslinkers were synthesized and characterized, including propiolate esters of di- and trifunctional alcohols, propargyl esters of di- and trifunctional carboxylic acids, propargyl ethers of di- and trifunctional alcohols, and N,N,N',N'-tetrapropargyl derivatives of primary diamines. Commercially available tripropargyl amine was also studied. Those systems employing a propiolate-based alkyne were found to be much more reactive toward the Huisgen 1,3-dipolar cycloaddition than the propargyl species. Curing energetics as a function of alkyne type, investigated through a dynamic differential scanning calorimetry approach, showed a distinct divide between the averaged activation energies of the propiolate and propargyl-type crosslinkers, 69.2-73.6 kJ/mol versus 82.3-86.4 kJ/mol, respectively. Cured network properties were readily manipulated through the incorporation of varying amounts of diversus tri- and tetra-functional alkynes or through incorporation of soft alkylene and alkyleneoxy versus rigid aromatic polyalkynes. As expected, mechanical properties, e.g., the temperature of the tan delta peak in dynamic mechanical analysis, were found to increase with increasing crosslink density. These results have allowed us to select the most promising systems for scale-up and fabrication of samples of both pure resin and composites for traditional mechanical property testing, which will be reported in a subsequent paper. (c) 2012 Elsevier Ltd. All rights reserved.
• NOVEL COMPOSITE COMPOSITIONS AND METHODS OF PREPARING AND USING SAME
  申请人：THE REGENTS OF THE UNIVERSITY OF COLORADO, A BODY CORPORATE

  公开号：US20150267002A1

  公开（公告）日：2015-09-24

  The present invention includes compositions comprising an alkyne-based substrate, an azide-based substrate, optionally a Cu(II) salt and optionally a photoinducible reducing agent. The present invention further includes a method of preparing composite materials that are suitable for use as dental implants using the compositions of the invention.