2H,2'H-4,4'-bichromene | 1384484-68-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2H,2'H-4,4'-bichromene
• 英文别名: 4-(2H-chromen-4-yl)-2H-chromene
• CAS: 1384484-68-7
• 化学式: C₁₈H₁₄O₂
• 分子量: 262.308
• InChiKey: WCGCNXILODSQEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2H,2'H-4,4'-bichromene 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以80%的产率得到4,11-dioxa-5,6,12,12a-tetrahydrobenzo[j]fluoranthene
  参考文献：
  名称：

  Hybrid System of Metal/Brønsted Acid Relay Catalysis for the Intramolecular Double Hydroarylation and Cationic Cyclization of Diyne Diethers and Diamines

  摘要：

  We have developed a hybrid system of metal/Bronsted acid relay catalysis for the intramolecular double hydroarylation and cationic cyclization of diyne diethers and diamines to give 4,4'-bi(2H-chromene), bi(2H-quinoline), and dioxafluoranthenes starting from 2,4-diyne-1,6-diethers and diamines in one reaction vessel under mild conditions.

  DOI：

  10.1021/ol301522y
• 作为产物：
  描述：

  苯基炔丙基醚 在 嘧啶 、 3H⁽¹⁺⁾*O₄₀SiW₁₂^(4-)*C₂₀H₁₈AuNP⁽¹⁺⁾ 、 copper(II) acetate monohydrate 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 2H,2'H-4,4'-bichromene
  参考文献：
  名称：

  Polyoxometalate-Gold(I)/H⁺ Complexes: Air-Stable, Efficient, Polyvalent, and Bifunctional Catalysts

  摘要：

  Gold(I)/H+-polyoxometalate hybrids, with general formula [POM](x-)[H](x-1)(+)[R3PAu(MeCN)](+), were synthesized and fully characterized by P-31 and Si-29 MAS or liquid NMR, FT-IR, and mass spectroscopy. All these polyoxometalate gold(I) complexes exhibited excellent catalytic activity and selectivity compared to standard homogeneous gold catalysts in a large range of reactions. The variation of the ligand and the polyoxometalate nature around gold(I) also highlighted the flexibility and the multifunctionality of such catalysts, as well as their recyclability.

  DOI：

  10.1021/acs.organomet.5b00656

文献信息

• Benzyne-Mediated Nonconcerted Pathway toward Synthesis of Sterically Crowded [5]- and [7]Oxahelicenoids, Stereochemical and Theoretical Studies, and Optical Resolution of Helicenoids
  作者：Prashant M. Gawade、Vaibhav N. Khose、Purav M. Badani、Mohammed Hasan、Sandra Kaabel、Shaikh M. Mobin、Victor Borovkov、Anil V. Karnik

  DOI：10.1021/acs.joc.8b02507

  日期：2019.1.18

  Synthesis of [5]- and [7]oxahelicenoids via Diels–Alder reaction of sterically crowded bichromenes with benzyne is presented. Studies carried out on Diels–Alder addition product establish the unusual preference for a stepwise mechanism over the concerted reaction pathway. This high yielding general synthetic protocol affords unexpected anti cycloadducts [5]- and [7]oxahelicenoids, as confirmed by crystallographic

  介绍了通过空间拥挤的双色酮与苯并炔的Diels-Alder反应合成[5]-和[7]氧杂萘的化合物。对Diels–Alder加成产物的研究建立了一种相对于一致的反应途径，更倾向于逐步机制的偏爱。如晶体学分析所证实的，这种高收率的通用合成方案提供了出乎意料的抗环加成物[5]-和[7]氧杂萘类化合物。为了合理化这些有趣的抗加成产物，通过DFT分析阐明了反应机理。另外，羟基官能化的[7]氧杂半萜烯类化合物已经以其光学纯净的形式拆分。
• Synthesis, Characterization, and Catalytic Activity of Cationic NHC Gold(III) Pyridine Complexes
  作者：Serena Orbisaglia、Béatrice Jacques、Pierre Braunstein、Damien Hueber、Patrick Pale、Aurélien Blanc、Pierre de Frémont

  DOI：10.1021/om400338k

  日期：2013.8.12

  A series of cationic gold(I/III) pyridine complexes of the type [(L)Au(pyr)](PF6) and [(L)AuCl2(pyr)](PF6), where L = IPr, (1, 5); L = IMes (2, 6); L = (IBu)-Bu-t, (3, 7); L = ICy (4, 8); and L = PPh3, (9, 10), were synthesized and characterized by NMR spectroscopy and single-crystal X-ray diffraction. The stability of the new complexes and their catalytic activity in five well-established organic transformations were assessed.