5-n-butylindan | 92013-22-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 5-n-butylindan
• 英文别名: 5-butylindan；5-Butyl-2,3-dihydro-1H-indene
• CAS: 92013-22-4
• 化学式: C₁₃H₁₈
• 分子量: 174.286
• InChiKey: UJGOUXAEHNPLGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  6-溴茚酮 在 platinum(IV) oxide sodium tetrahydroborate 、 [nickel(II)dichloride(1,3-bis(diphenylphosphino)propane)] 、 氢气 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 苯 为溶剂， 25.0 ℃ 、137.9 kPa 条件下， 生成 5-n-butylindan
  参考文献：
  名称：

  Synthesis of biological markers in fossil fuels. 2. Synthesis and carbon-13 NMR studies of substituted indans and tetralins

  摘要：

  DOI：

  10.1021/jo00196a024

文献信息

• Formal radical closure onto aromatic rings—a general route to carbocycles
  作者：Derrick L. J. Clive、Rajesh Sunasee、Zhenhua Chen

  DOI：10.1039/b803308k

  日期：——

  A general method is described for indirectly effecting radical carbocyclization of an alkyl chain onto an aromatic ring. Birch reductive-alkylation of aromatic tert-butyl esters with α,ω-dibromides, chromium(VI)-mediated oxidation of the resulting 1,4-dienes and Finkelstein displacement of Br− with NaI gives cross-conjugated ketones that undergo radical cyclization. The products are easily aromatized to phenols by silylation, Saegusa oxidation and treatment with BiCl3.H2O. A special feature of the route is that it allows attachment of a substituent to the original aromatic ring in place of the phenolic oxygen of the normal product.

  一种通用方法被描述用于间接地实现烷基链与芳环的自由基碳环化。通过使用α,ω-二溴化物对芳香叔丁基酯进行Birch还原烷基化，接着对所得的1,4-二烯进行铬(VI)介导的氧化，以及用NaI替代Br⁻的Finkelstein反应，可以得到交联共轭酮，这些酮随后经历自由基环化。这些产物可以通过硅化、Saegusa氧化以及与BiCl3·H2O处理，轻松芳香化为酚类化合物。这条路线的一个特殊之处在于，它允许将取代基附加到原始芳环上，以替代正常产物中的酚醇氧。
• Iridium Complex-Catalyzed [2+2+2] Cycloaddition of α,ω-Diynes with Monoynes and Monoenes
  作者：Satoko Kezuka、Shigeru Tanaka、Toshihito Ohe、Yoshihiko Nakaya、Ryo Takeuchi

  DOI：10.1021/jo051874c

  日期：2006.1.1

  [Ir(cod)Cl](2)/DPPE was found to be a new catalyst for the cycloaddition of alpha,omega-diynes with monoynes to give polysubstituted benzene derivatives in high yields. Internal monoynes as well as terminal monoynes could be used. The reaction tolerates a broad range of functional groups such as alcohol, amine, alkene, ether, halogen, and nitrile. The reaction of 1,6-octadiyne derivatives with 1-alkynes gives ortho products and meta products. The regioselectivity could be controlled by the choice of ligand. The reaction with DPPE was meta selective, with meta selectivity of up to 82%. The reaction with DPPF was ortho selective, with ortho selectivity of up to 88%. We propose a mechanism to account for this regioselective cycloaddition. [Ir(cod)Cl-2]2/DPPE also catalyzed the cycloaddition of alpha-omega-diynes with 2,5-dihydrofuran to give bicyclic cyclohexadiene derivatives. The reaction with 2,3-dihydrofuran and n-butyl vinyl ether gave benzene derivatives instead of cyclohexadiene derivatives. We also propose a mechanism to account for this novel aromatization that includes cleavage of the C-O bond.
• Grigg, Ronald; Scott, Ronald; Stevenson, Paul, Journal of the Chemical Society. Perkin transactions I, 1988, p. 1357 - 1364
  作者：Grigg, Ronald、Scott, Ronald、Stevenson, Paul

  DOI：——

  日期：——
• ADAMCZYK, M.;WATT, D. S.;NETZEL, D. A., J. ORG. CHEM., 1984, 49, N 22, 4226-4237
  作者：ADAMCZYK, M.、WATT, D. S.、NETZEL, D. A.

  DOI：——

  日期：——
• Synthesis of biological markers in fossil fuels. 2. Synthesis and carbon-13 NMR studies of substituted indans and tetralins
  作者：Maciej Adamczyk、David S. Watt、Daniel A. Netzel

  DOI：10.1021/jo00196a024

  日期：1984.11