6,8-di-tert-butyl-2-phenyl-2,3-dihydro<4H>benzopyran | 76336-91-9

• 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: 6,8-di-tert-butyl-2-phenyl-2,3-dihydro<4H>benzopyran
• 英文别名: 6,8-di-t-butyl-2-phenyl-2,3-dihydro[4H]benzopyran；6,8-di-tert-butyl-2-phenylchroman；6,8-Di-t-butylflavan；flavan；6,8-ditert-butyl-2-phenyl-3,4-dihydro-2H-chromene
• CAS: 76336-91-9
• 化学式: C₂₃H₃₀O
• 分子量: 322.491
• InChiKey: ZEJOSTZDFLFPOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 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：

  2,4-二叔丁基苯酚钠 以 正己烷 、 苯 为溶剂， 反应 6.0h， 生成 6,8-di-tert-butyl-2-phenyl-2,3-dihydro<4H>benzopyran
  参考文献：
  名称：

  苯酚-苯乙烯双大分子系统中分子内的激发态相互作用：光化学和光物理研究

  摘要：

  已直接观察到一系列在酚环上带有给电子取代基的反式-2-肉桂基苯酚中苯酚和苯乙烯之间的分子内激发态相互作用，作为乙腈中的激基复合物发射。与模型化合物相比，光化学反应性和相对较低的荧光量子产率是苯酚/苯乙烯相互作用的其他证据。

  DOI：

  10.1016/s0040-4020(01)01132-2

文献信息

• Gold(I)-catalysed one-pot synthesis of chromans using allylic alcohols and phenols
  作者：Eloi Coutant、Paul C Young、Graeme Barker、Ai-Lan Lee

  DOI：10.3762/bjoc.9.209

  日期：——

  A gold(I)-catalysed reaction of allylic alcohols and phenols produces chromans regioselectively via a one-pot Friedel-Crafts allylation/intramolecular hydroalkoxylation sequence. The reaction is mild, practical and tolerant of a wide variety of substituents on the phenol.

  烯丙醇和酚的金 (I) 催化反应通过一锅 Friedel-Crafts 烯丙基化/分子内加氢烷氧基化序列区域选择性地产生色满。该反应温和、实用且可耐受苯酚上的多种取代基。
• Cubic Pm3n mesoporous aluminosilicates assembled from zeolite seeds as strong acidic catalysts
  作者：Tsung-Han Lin、Chia-Han Chen、Chi-Shuang Chang、Ming-Chang Liu、Shing-Jong Huang、Soofin Cheng

  DOI：10.1039/c5cy00184f

  日期：——

  Pm3n mesoporous aluminosilicates isomorphous to SBA-1, with 3D interconnected pore structures, were assembled from Al-incorporating zeolite seeds at around pH 9 using cetyltriethylammonium bromide as a pore-directing agent. The resultant series of materials (termed Al–ZSBA-1) has the advantages of strong acidity from the zeolitic structure and good diffusivity of bulky reactants from the 3D interconnected

  使用十六烷基三乙基溴化铵作为导孔剂，从pH约为9的掺铝沸石种子中，组装了与SBA-1同构的立方Pm 3 n介孔铝硅酸盐，并在其中加入了Al分子筛种子。所得的一系列材料（称为Al–ZSBA-1）具有沸石结构的强酸性和3D互连中孔的大体积反应物良好扩散性的优点。Al–ZSBA-1，Al含量高达0.057的Al / Si时，仍保留了立方Pm 3 n结构和高表面积（约600 m 2 g -1）。酸度强于使用硅酸钠作为二氧化硅源（称为Al–SBA-1-alk）制备的相对材料。此外，Al–ZSBA-1中的所有Al（III）离子在823 K下煅烧后仍保持其四面体配位，而Al–SBA-1-alk中的部分Al（III）变为八面体配位。当测试肉桂醇对2,4-二叔丁基苯酚的催化烷基化反应时，与Al-SBA-1-alk，ZSM-5和β沸石相比，Al-ZSBA-1具有更高的黄烷选择性和产率。
• 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。
• Aluminium-containing mesoporous benzene-silicas with crystal-like pore wall structure
  作者：Qihua Yang、Jie Yang、Zhaochi Feng、Ying Li

  DOI：10.1039/b507437a

  日期：——

  Mesoporous benzene-silicas with a high content of tetrahedral aluminium in the framework (Si/Al = 37 and 59) were successfully synthesized, as evidenced by X-ray diffraction, N2 sorption analyses, transmission electron microscopy and solid state 13C CP-MAS, 27Al and 29Si MAS NMR spectroscopy. These materials have well-ordered 2D hexagonal mesostructure with a molecular scale periodicity in the pore walls. The existence of the phenylene groups in the framework greatly enhances the hydrothermal stability of the aluminium-containing mesoporous benzene-silicas. The acidity of the mesoporous benzene-silicas arising from the incorporated aluminium was measured by the FT-IR spectra of pyridine adsorption measurements. The organic groups bridged in the mesoporous framework affect significantly the acidity of the resultant materials although most aluminium atoms are in tetrahedral coordination. These materials are catalytically active for alkylation of 2,4-di-tert-butylphenol with cinnamyl alcohol.

  通过 X 射线衍射、N2 吸附分析、透射电子显微镜和固态 13C CP-MAS、27Al 和 29Si MAS NMR 光谱，成功合成了框架中含有大量四面体铝（Si/Al = 37 和 59）的介孔苯硅。这些材料具有井然有序的二维六边形介观结构，孔壁具有分子尺度的周期性。框架中苯基基团的存在大大提高了含铝介孔苯硅胶的水热稳定性。通过对吡啶吸附的傅立叶变换红外光谱测量，得出了因加入铝而产生的介孔苯硅胶的酸性。尽管大多数铝原子都是四面体配位，但介孔框架中桥接的有机基团对生成材料的酸度有很大影响。这些材料对 2,4- 二叔丁基苯酚与肉桂醇的烷基化具有催化活性。