6-tert-butyl-2-phenyl-2,3-dihydro<4H>benzopyran | 76336-93-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 6-tert-butyl-2-phenyl-2,3-dihydro<4H>benzopyran
• 英文别名: 6-t-Butylflavan；6-tert-butyl-2-phenyl-3,4-dihydro-2H-chromene
• CAS: 76336-93-1
• 化学式: C₁₉H₂₂O
• 分子量: 266.383
• InChiKey: NDNGJPKJUAHYMA-UHFFFAOYSA-N

物化性质

• 熔点：
  70 °C(Solv: methanol (67-56-1))
• 沸点：
  376.1±42.0 °C(Predicted)
• 密度：
  1.031±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  6-(tert-butyl)-2-phenyl-2H-chromene 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到6-tert-butyl-2-phenyl-2,3-dihydro<4H>benzopyran
  参考文献：
  名称：

  Synthesis of 3-Iodoflavans and 2H-Flavenes

  摘要：

  DOI：

  10.1055/s-1980-29139

文献信息

• Selective synthesis of 6,8-di-t-butylated flavan over Zn–Al containing mesoporous silica catalysts
  作者：M. Selvaraj、P. K. Sinha、D.-W. Park、Il Kim、S. Kawi、C. S. Ha

  DOI：10.1039/c2dt31409f

  日期：——

  We demonstrate a much green synthesis method for highly selective synthesis of 6,8-di-t-butylated flavan (6,8-DTBF) by liquid phase alkylation of 2,4-di-t-butylphenol (2,4-DTBP) with cinnamyl alcohol (Cin-OH) over mesoporous Zn–Al–MCM-41 catalysts synthesized under direct basic hydrothermal method. The main alkylated product, 6,8-DTBF is importantly used as an intermediate in the manufacture of biosynthetic organic compounds. The recyclable mesoporous Zn–Al–MCM-41 catalysts have also been reused in this reaction to study their catalytic activities. The influences of various reaction parameters such as temperature, time, ratios of reactant (2,4-DTBP-to-Cin-OH) have been extensively investigated for the synthesis of 6,8-DTBF. In addition, dimethyl sulfoxide (DMSO) has also been used as a solvent in this catalytic reaction. The mesoporous Zn–Al–MCM-41(75) gives excellent catalytic activity with 6,8-DTBF selectivity (86.0%) and 2,4-DTBP conversion (63.1%), and these catalytic results have also compared with that obtained using other mesoporous and microporous catalysts. On the basis of catalytic activity obtained by using the all catalysts, the Zn–Al–MCM-41(75) catalyst is found to be a highly active, recyclable and eco-friendly heterogeneous catalyst in the liquid-phase alkylation of 2,4-DTBP.

  我们展示了一种通过 2,4-二叔丁基苯酚 (2,4-DTBP) 液相烷基化高选择性合成 6,8-二叔丁基黄烷 (6,8-DTBF) 的绿色合成方法直接碱性水热法合成的介孔Zn-Al-MCM-41催化剂上与肉桂醇(Cin-OH)的反应。主要烷基化产品 6,8-DTBF 在生物合成有机化合物的生产中被重要用作中间体。可回收的介孔Zn-Al-MCM-41催化剂也被重复用于该反应，以研究其催化活性。人们广泛研究了各种反应参数（例如温度、时间、反应物比例（2,4-DTBP-to-Cin-OH））对 6,8-DTBF 合成的影响。此外，二甲基亚砜（DMSO）也被用作该催化反应的溶剂。介孔Zn-Al-MCM-41(75)具有优异的催化活性，6,8-DTBF选择性(86.0%)和2,4-DTBP转化率(63.1%)，这些催化结果也与使用其他介孔和微孔催化剂获得。基于所有催化剂的催化活性，发现Zn-Al-MCM-41(75)催化剂在2的液相烷基化反应中是一种高活性、可回收且环境友好的多相催化剂。 ,4-DTBP。
• Mesoporous aluminosilicate MCM-41 as a convenient acid catalyst for Friedel–Crafts alkylation of a bulky aromatic compound with cinnamyl alcohol
  作者：Elvira Armengol、María L. Cano、Avelino Corma、Hermenegildo García、María T. Navarro

  DOI：10.1039/c39950000519

  日期：——

  Owing to its large molecular size, alkylation of 2,4-di-tert-butylphenol with cinnamyl alcohol does not take plAcc using HY zeolite (pore opening 7.4 Å) as catalyst even after controlled steaming treatment to increase its mesoporosity; by contrast, novel mesoporous aluminosilicate MCM-41 catalyses this reaction giving rise to 6,8-di-tert-butyl-2-phenyl-2,3-dihydro[4H]benzopyran (arising from intramolecular cyclization of the primary cinnamylphenol) together with 4-tert-butylphenol and small amounts of 6-tert-butyl-2-phenyl-2,3-dihydro[4H]benzopyran.

  由于 2,4-二叔丁基苯酚的分子尺寸较大，使用 HY 沸石（孔开度 7.4 Ã ）作为催化剂，即使经过控制蒸煮处理以增加其介孔率，也不会发生烷基化反应；相比之下，新型介孔铝硅酸盐 MCM-41 可催化这一反应，生成 6,8- 二叔丁基-2-苯基-2,3-二氢[4H]苯并吡喃（由初级肉桂基苯酚的分子内环化产生）以及 4-叔丁基苯酚和少量 6-叔丁基-2-苯基-2,3-二氢[4H]苯并吡喃。
• JURD L.; MANNERS G. D., SYNTHESIS, 1980, NO 8, 618-619
  作者：JURD L.、 MANNERS G. D.

  DOI：——

  日期：——