1,3,5-tris((allyloxy)methyl)benzene | 1158483-15-8

• 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-tris((allyloxy)methyl)benzene
• 英文别名: 1,3,5-Tris(prop-2-enoxymethyl)benzene
• CAS: 1158483-15-8
• 化学式: C₁₈H₂₄O₃
• 分子量: 288.387
• InChiKey: NAWXQCHGQPMDSC-UHFFFAOYSA-N

物化性质

• 沸点：
  367.8±37.0 °C(predicted)
• 密度：
  0.989±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  1,3,5-tris((allyloxy)methyl)benzene 、 溴甲苯 在 六羰基铬 、 正丁基锂 、 (1S,2S)-1,2-diphenyl-N,N'-bis((R)-1-phenylethyl)ethane-1,2-diamine 、 lithium chloride 作用下， 以 四氢呋喃 、 二丁醚 、 正己烷 为溶剂， 反应 25.0h， 以138 mg的产率得到(-)-(R)-1,3,5-tris(1-allyloxy-2-phenylethyl)benzene
  参考文献：
  名称：

  通过苄基烯丙基醚的三羰基铬(0)配合物合成对映体富集的仲醇和叔醇

  摘要：

  苄醇的三羰基铬 (0) 络合物的烯丙基醚使用手性碱/亲电子猝灭序列进行高度对映选择性的苄基官能化；如对映体富集的咪唑醇、三醇和叔醇的合成所证明的，烯丙基很容易去除以显示羟基。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  DOI：

  10.1002/ejoc.200900007
• 作为产物：
  描述：

  1,3,5-三(溴甲基)苯 、 烯丙醇 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.17h， 以86%的产率得到1,3,5-tris((allyloxy)methyl)benzene
  参考文献：
  名称：

  Thermomechanical Formation–Structure–Property Relationships in Photopolymerized Copper-Catalyzed Azide–Alkyne (CuAAC) Networks

  摘要：

  Bulk photopolymerization of a library of synthesized multifunctional azides and alkynes was carried out toward developing structure property relationships for CuAAC-based polymer networks. Multifunctional azides and alkynes were formulated with a copper catalyst and a photoinitiator, cured, and analyzed for their mechanical properties. Material properties such as the glass transition temperatures (T-g) show a strong dependence on monomer structure with T-g values ranging from 41 to 90 degrees C for the series of CuAAC monomers synthesized in this study. Compared to the triazoles, analogous thioether-based polymer networks exhibit a 45-49 degrees C lower T-g whereas analogous monomers composed of ethers in place of carbamates exhibit a 40 degrees C lower T-g. Here, the formation of the triazole moiety during the polymerization represents a critical component in dictating the material properties of the ultimate polymer network where material properties such as the rubbery modulus, cross-link density, and T-g all exhibit strong dependence on polymerization conversion, monomer composition, and structure postgelation.

  DOI：

  10.1021/acs.macromol.6b00137

文献信息

• Iron-catalyzed regioselective cyclotrimerization of alkynes to benzenes
  作者：Suhas Shahaji Gawali、Chidambaram Gunanathan

  DOI：10.1016/j.jorganchem.2018.12.007

  日期：2019.2

  catalyzed the regioselective [2+2+2] cyclotrimerization of terminal aryl and alkyl alkynes to provide the 1,2,4-trisubstituted benzene molecules. Interestingly, internal alkynes also exhibited similar cyclization and resulted in hexa-substituted benzene compounds. Increased steric bulk on pincer ligands diminished the selectivity for cycloaddition. Cyclotrimerization reactions proceeded at room temperature

  我们报告了简单的二（氨基甲基）吡啶连接的铁-钳配合物的合成和表征，它催化了末端芳基和烷基炔烃的区域选择性[2 + 2 + 2]环三聚反应，从而提供了1,2,4-三取代的苯分子。有趣的是，内部炔烃也表现出相似的环化作用，并产生六取代的苯化合物。钳位配体上增加的空间体积减少了对环加成反应的选择性。在通过格氏试剂活化催化剂后，在室温下进行环三聚反应。EPR研究表明，在催化剂中热诱导的自旋交叉效应。
• Thermomechanical Formation–Structure–Property Relationships in Photopolymerized Copper-Catalyzed Azide–Alkyne (CuAAC) Networks
  作者：Austin Baranek、Han Byul Song、Mathew McBride、Patricia Finnegan、Christopher N. Bowman

  DOI：10.1021/acs.macromol.6b00137

  日期：2016.2.23

  Bulk photopolymerization of a library of synthesized multifunctional azides and alkynes was carried out toward developing structure property relationships for CuAAC-based polymer networks. Multifunctional azides and alkynes were formulated with a copper catalyst and a photoinitiator, cured, and analyzed for their mechanical properties. Material properties such as the glass transition temperatures (T-g) show a strong dependence on monomer structure with T-g values ranging from 41 to 90 degrees C for the series of CuAAC monomers synthesized in this study. Compared to the triazoles, analogous thioether-based polymer networks exhibit a 45-49 degrees C lower T-g whereas analogous monomers composed of ethers in place of carbamates exhibit a 40 degrees C lower T-g. Here, the formation of the triazole moiety during the polymerization represents a critical component in dictating the material properties of the ultimate polymer network where material properties such as the rubbery modulus, cross-link density, and T-g all exhibit strong dependence on polymerization conversion, monomer composition, and structure postgelation.
• Synthesis of Enantioenriched Secondary and Tertiary Alcohols via Tricarbonylchromium(0) Complexes of Benzyl Allyl Ethers
  作者：Keren Abecassis、Susan E. Gibson、Mar Martin-Fontecha

  DOI：10.1002/ejoc.200900007

  日期：2009.4

  Allyl ethers of the tricarbonylchromium(0) complexes of benzylic alcohols undergo highly enantioselective benzylic functionalisation using a chiral base/electrophilic quench sequence; the allyl group is readily removed to reveal a hydroxy group as demonstrated in the syntheses of enantioenriched imidazole alcohols, a triol and a tertiary alcohol. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim

  苄醇的三羰基铬 (0) 络合物的烯丙基醚使用手性碱/亲电子猝灭序列进行高度对映选择性的苄基官能化；如对映体富集的咪唑醇、三醇和叔醇的合成所证明的，烯丙基很容易去除以显示羟基。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)