1,3,5-benzenetrimethanol 1,3,5-tripropiolate | 1382353-48-1

• 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: 1,3,5-benzenetrimethanol 1,3,5-tripropiolate
• 英文别名: [3,5-Bis(prop-2-ynoyloxymethyl)phenyl]methyl prop-2-ynoate；[3,5-bis(prop-2-ynoyloxymethyl)phenyl]methyl prop-2-ynoate
• CAS: 1382353-48-1
• 化学式: C₁₈H₁₂O₆
• 分子量: 324.29
• InChiKey: NEEVFJKWIYWKRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-频哪醇-2-(1,8)萘二胺联硼酸酯 、 1,3,5-benzenetrimethanol 1,3,5-tripropiolate 在 (叔丁基亚氨基)三(吡咯烷)膦 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以65%的产率得到C₆₆H₇₂B₆N₆O₁₂
  参考文献：
  名称：

  有机超碱催化炔烃的 1,1-二硼化

  摘要：

  1,1-二硼基烯烃是有机合成和药物化学中的通用组成部分。然而，目前只有少数成熟的方法来制备这类化合物，并且大多数使用过渡金属催化剂，这在生物相关化合物的制备中是不可取的。进来，我们报告一个前所未有的 P 1 – t应用Bu 磷腈作为超碱性有机催化剂促进未活化的芳香族和缺电子末端炔烃的 1,1-二硼化反应。这种磷腈的双 Brønsted 和 Lewis 碱度能够激活反应底物并获得高区域和立体选择性。彻底的实验和计算研究相结合，为这些磷腈催化的二硼化反应提出了有趣的机理见解，这些反应也得到了详细讨论。

  DOI：

  10.1021/acscatal.2c03901
• 作为产物：
  描述：

  均三苄醇 、 丙炔酸 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 4.5h， 生成 1,3,5-benzenetrimethanol 1,3,5-tripropiolate
  参考文献：
  名称：

  Development of a triazole-cure resin system for composites: Evaluation of alkyne curatives

  摘要：

  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.

  DOI：

  10.1016/j.polymer.2012.04.002

文献信息

• 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.
• Organosuperbase-Catalyzed 1,1-Diboration of Alkynes
  作者：Son H. Doan、Nhan N. H. Ton、Binh Khanh Mai、Thanh Vinh Nguyen

  DOI：10.1021/acscatal.2c03901

  日期：2022.10.7

  1,1-Diboryl alkenes are versatile building blocks in organic synthesis and medicinal chemistry. However, there have been only a small number of established methods to prepare this class of compounds, and most of them used transition-metal catalysts, which are undesirable in the preparation of biologically relevant compounds. Herein, we report an unprecedented application of P1–tBu phosphazene as a

  1,1-二硼基烯烃是有机合成和药物化学中的通用组成部分。然而，目前只有少数成熟的方法来制备这类化合物，并且大多数使用过渡金属催化剂，这在生物相关化合物的制备中是不可取的。进来，我们报告一个前所未有的 P 1 – t应用Bu 磷腈作为超碱性有机催化剂促进未活化的芳香族和缺电子末端炔烃的 1,1-二硼化反应。这种磷腈的双 Brønsted 和 Lewis 碱度能够激活反应底物并获得高区域和立体选择性。彻底的实验和计算研究相结合，为这些磷腈催化的二硼化反应提出了有趣的机理见解，这些反应也得到了详细讨论。