2,4-diphenyl-3,6-dihydro-2H-pyran | 71188-55-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2,4-diphenyl-3,6-dihydro-2H-pyran
• 英文别名: 2-phenyl-4-phenyl-3,6-dihydro-2H-pyrane
• CAS: 71188-55-1
• 化学式: C₁₇H₁₆O
• 分子量: 236.313
• InChiKey: QPJUWHMKAYXQSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 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-Phenyl-4-methyl-4-phenyl-1,3-dioxane 、 硫酸 以25%的产率得到
  参考文献：
  名称：

  POMAHOB, N. A.;KANTOR, E. A.;MUSAVIROV, R. S.;KARAXANOV, R. A.;RAXMANKULO+, ZH. PRIKL. XIMII, 1982, 55, N 1, 157-161

  摘要：

  DOI：

文献信息

• Silver Tetrafluoroborate-Catalyzed Oxa-Diels-Alder Reaction Between Electrically Neutral Dienes and Aldehydes
  作者：Xiaodong Zou、Lizheng Yang、Xiangli Liu、Hao Sun、Hongjian Lu

  DOI：10.1002/adsc.201500487

  日期：2015.10.12

  Chemoselective oxa-Diels–Alder reactions between electrically neutral 1,3-dienes and various aldehydes were achieved using the commercially available silver tetrafluoroborate (AgBF4) as catalyst. This catalytic process has high functional group tolerance. Heteroatoms at the β-position of the aryl aldehydes can greatly promote the reactivity of the substrates even with heterocyclic aldehydes that were

  使用市售的四氟硼酸银（AgBF 4）作为催化剂，可以实现电中性1,3-二烯与各种醛之间的化学选择性oxa-Diels-Alder反应。该催化过程具有较高的官能团耐受性。即使以前认为杂环醛对oxa-Diels-Alder反应没有反应性，芳基醛的β-位上的杂原子也可以极大地提高底物的反应性。另外，具有β-杂原子取代的丙烯醛也是良好的底物。室温下，丙烯醛与化学计量简单的1,3-二烯之间的oxa-Diels-Alder反应实现了高化学选择性和区域选择性。
• Iron Corrole-catalyzed [4 + 2] Cycloaddition of Dienes and Aldehydes
  作者：Toru Kuwano、Takuya Kurahashi、Seijiro Matsubara

  DOI：10.1246/cl.130672

  日期：2013.10.5

  We have developed cationic iron(IV) corrole-catalyzed formal hetero-Diels–Alder reaction of aldehydes with dienes, which opens the way for divergent synthesis of pyrans. The potential utility of the catalyst was also demonstrated by carrying out cycloaddition of α,β-unsaturated aldehyde with a diene to give pyran selectively. Furthermore, the catalytic reactivity of iron corrole complex on the cycloaddition was determined by comparing that of iron porphyrin complex.

  我们开发了一种阳离子铁(IV) corrole 催化的醛与二烯的正式杂-Diels-Alder 反应，这为吡喃的多样性合成开辟了道路。催化剂的潜在应用价值也通过 α,β-不饱和醛与二烯的环加成反应得到选择性吡喃的生成得以证明。此外，通过比较铁 porphyrin 配合体在环加成反应中的催化活性，确定了铁 corrole 配合体的催化反应活性。
• AlCl3 catalyzed oxa-Diels-Alder reaction of aromatic aldehydes with simple dienes
  作者：Wujun Jian、Bo Qian、Hongli Bao、Daliang Li

  DOI：10.1016/j.tet.2016.10.049

  日期：2017.7

  A highly regioselective and diastereoselective oxa-Diels-Alder reaction catalyzed by AlCl3 has been developed. This reaction is efficient and characterized by good functional group compatibility, F, Cl, CN, NO2, OMe and thiophenyl groups are tolerated. A Lewis acid catalyzed concerted cycloaddition mechanism is proposed based on the results.

  已经开发了由AlCl 3催化的高度区域选择性和非对映选择性的oxa-Diels-Alder反应。该反应是有效的并且以良好的官能团相容性为特征，可以容忍F，Cl，CN，NO 2，OMe和硫代苯基。基于该结果，提出了路易斯酸催化的协同环加成机理。
• Efficient Synthesis of 3,6‐Dihydro‐2H‐pyrans via [3+2+1] Annulation Based on the Heteroatom‐free Tri‐atom Donor
  作者：Hui Li、Haiping Liu、Yufeng Liu、Zhongzhong Cao、Miaodong Su、Meiqiang Fu、Weiping Luo、Qiang Liu、Cancheng Guo

  DOI：10.1002/adsc.201900900

  日期：2019.12.3

  strategy based on the heteroatom‐free tri‐atom donor to synthesize 3,6‐dihydro‐2H‐pyrans has been developed. In this method, 2‐arylpropylene served as tri‐atom donor to contribute three carbon atoms, the heteroatom was provided by aldehyde, and DMSO served as one carbon donor and solvent. This annulation reaction gave 3,6‐dihydro‐2H‐pyrans in moderate to good yields. Based on the control experiments, a

  基于无杂原子的三原子供体合成3,6-二氢-2 H-吡喃的新的[3 + 2 + 1]环空策略已被开发出来。在这种方法中，2-芳基丙烯充当三原子供体，贡献三个碳原子，杂原子由醛提供，而DMSO作为一种碳供体和溶剂。此成环反应产生3,6-dihydro-2 H-吡喃，产率中等至良好。在控制实验的基础上，提出了一种可能的机理。
• Ligand-Directed Conformational Control over Porphyrinic Zirconium Metal–Organic Frameworks for Size-Selective Catalysis
  作者：Liting Yang、Peiyu Cai、Liangliang Zhang、Xiaoyi Xu、Andrey A. Yakovenko、Qi Wang、Jiandong Pang、Shuai Yuan、Xiaodong Zou、Ning Huang、Zhehao Huang、Hong-Cai Zhou

  DOI：10.1021/jacs.1c03960

  日期：2021.8.11

  sizes could limit the accessibility of substrates to active centers in the framework. On the basis of the structural characteristics, PCN-625(Fe) can be utilized as an efficient heterogeneous catalyst for the size-selective [4 + 2] hetero-Diels–Alder cycloaddition reaction. Due to its high chemical stability, this catalyst can be repeatedly used over six times. This work demonstrates that Zr-MOFs can

  锆基金属有机骨架（Zr-MOFs）由于其优异的稳定性、柔性结构和有趣的功能而引起了极大的兴趣。精确控制其晶体结构，包括拓扑结构、孔隙率、组成和构象，是实现定制功能化的重要挑战。在这项工作中，我们开发了一种新的 Zr-MOF (PCN-625) 与csq拓扑网络，类似于著名的 PCN-222 和 NU-1000。然而，显着差异在于卟啉环的构象，它们垂直于孔表面而不是平行。由此产生的 PCN-625 展示了两种类型的一维通道，混凝土直径为 2.03 和 0.43 nm。此外，垂直卟啉与收缩的孔径一起可能会限制底物对框架中活性中心的可及性。基于其结构特征，PCN-625(Fe)可用作尺寸选择性[4+2]杂-Diels-Alder环加成反应的有效多相催化剂。由于其化学稳定性高，这种催化剂可以重复使用六次以上。