5,6,7,8-Tetrahydro-2-butyl-4H-cycloheptafuran | 89506-69-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5,6,7,8-Tetrahydro-2-butyl-4H-cycloheptafuran
• 英文别名: 2-butyl-5,6,7,8-tetrahydro-4H-cyclohepta[b]furan；3-butyl-5,6,7,8-tetrahydro-4H-cyclohepta[b]furan；5,6,7,8-Tetrahydro-2-butyl-4H-cyclohepta[b]furan
• CAS: 89506-69-4
• 化学式: C₁₃H₂₀O
• 分子量: 192.301
• InChiKey: FCJMEVCHQCMOQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-[(二甲氨基)甲基]环庚烷-1-酮 在 3-苄基羟乙基甲基噻唑氯化锂 硫酸 、 三乙胺 作用下， 以 乙醇 为溶剂， 60.0~550.0 ℃ 、1.33 kPa 条件下， 反应 63.0h， 生成 5,6,7,8-Tetrahydro-2-butyl-4H-cycloheptafuran
  参考文献：
  名称：

  Stetter, Hermann; Haese, Wilfried, Chemische Berichte, 1984, vol. 117, # 2, p. 682 - 693

  摘要：

  DOI：

文献信息

• Gold(III) Bromide Catalyzed Furannulation of 2-Alkynylcycloalk-2-enols: An Expedient Route to Fused Furans
  作者：P. Perumal、C. Praveen、P. Kiruthiga

  DOI：10.1055/s-0029-1217517

  日期：2009.7

  An efficient synthesis of fused furans from 2-alkynyl­cycloalk-2-enols via gold(III) bromide catalyzed cycloisomerization was achieved. The reaction condition is moderate and amenable to structurally diverse substrates, leading to good yield of products.

  通过金(III)溴化物催化的环异构化作用，从2-炔基环烯-2-烯醇高效合成了并环呋喃。反应条件温和且适用于结构多样的底物，从而获得良好的产率。
• Extrapolation of the gold-catalyzed cycloisomerization to the palladium-catalyzed cross-coupling/cycloisomerization of acetylenic alcohols for the synthesis of polysubstituted furans: Scope and application to tandem processes
  作者：Chandrasekar Praveen、Paramasivan T. Perumal

  DOI：10.1016/s1872-2067(15)60994-9

  日期：2016.2

  of diverse furan derivatives from acetylenic alcohols by gold and palladium catalyzed π-activation chemistry. Notably, this new method was found to be amenable to cyclooctyl-containing substrates, which represents a significant extension to this methodology compared with our previous reports. Furthermore, this newly developed method allowed for the direct construction of cyclooctyl furans from their

  摘要 本文描述了通过金和钯催化的 π 活化化学从炔醇制备多种呋喃衍生物的综合方法的发展。值得注意的是，发现这种新方法适用于含环辛基的底物，与我们之前的报告相比，这代表了对该方法的显着扩展。此外，这种新开发的方法允许在 Sonogashira 条件下从其合成前体直接构建环辛基呋喃。实验结果表明，钯在这些反应中起两个主要作用，包括（1）底物交叉偶联反应中必不可少的催化剂；(2) 通过典型的 π 活化过程促进炔醇中间体的环化。3-碘呋喃的一锅合成强调了这种化学的范围，这为进一步功能化（通过偶联方法）提供了机会。最后，AuBr 3 协议还详细阐述了多米诺环化/C-H 活化反应，以及无环前体的环化。总之，这项研究的结果表明，金和钯催化剂可用于在环化反应中相互补充。
• Silver(I)-Catalyzed Cascade: Direct Access to Furans from Alkynyloxiranes
  作者：Aurélien Blanc、Katharina Tenbrink、Jean-Marc Weibel、Patrick Pale

  DOI：10.1021/jo900483m

  日期：2009.6.5

  Functionalized furans are conveniently formed by a new silver(I)-catalyzed reaction of alk-1-ynyl oxiranes in the presence of p-toluenesulfonic acid and methanol. Evidence supported a cascade mechanism.
• Polyoxometalate-Gold(I)/H⁺ Complexes: Air-Stable, Efficient, Polyvalent, and Bifunctional Catalysts
  作者：Damien Hueber、Marie Hoffmann、Pierre de Frémont、Patrick Pale、Aurélien Blanc

  DOI：10.1021/acs.organomet.5b00656

  日期：2015.10.26

  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.
• Synthesis, Characterization, and Catalytic Activity of Alcohol-Functionalized NHC Gold(I/III) Complexes
  作者：Béatrice Jacques、Damien Hueber、Sophie Hameury、Pierre Braunstein、Patrick Pale、Aurélien Blanc、Pierre de Frémont

  DOI：10.1021/om500240h

  日期：2014.5.12

  A series of alcohol-functionalized NHC gold(I/III) complexes of the types [(L)Au(Cl or NTf2)] and [(L)AuCl3] (L = IPrEtOH, (1, 4, 5), IMesEtOH (2, 6), IMeEtOH (3, 7)) was readily synthesized and characterized by NMR spectroscopy and single-crystal X-ray diffraction. The catalytic activity of the new complexes was assessed and compared with that of other gold catalysts, in the tandem 3,3-rearrangement-Nazarov reactions of enynyl acetate and the rearrangement reaction of alkynyloxirane. The new complexes appeared to be dual-site catalysts in both transformations, thanks to the presence of the primary alcohol function tethered to the NHC ligands.