2,3-dibutyl-1H-inden-1-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 2,3-dibutyl-1H-inden-1-one
• 英文别名: 2,3-di-n-butylinden-1-one；2,3-dibutyl-1-indone；2,3-Dibutylinden-1-one
• 化学式: C₁₇H₂₂O
• 分子量: 242.361
• InChiKey: HAKYVCDRJQIACS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5-癸炔 、 2-碘苄醇 在 二氯双[二叔丁基-(4-二甲基氨基苯基)膦]钯(II) 、 氧气 、 potassium carbonate 作用下， 以 水 为溶剂， 反应 24.0h， 以77%的产率得到2,3-dibutyl-1H-inden-1-one
  参考文献：
  名称：

  Palladium-Catalyzed Annulation of Alkynes with Ortho-Halide-Containing Benzyl Alcohols in Aqueous Medium

  摘要：

  The Pd-catalyzed annulations of ortho-halide-containing benzyl alcohols with alkynes for the synthesis of indenones were achieved in aqueous Triton X-100 micelles with good yields and wide substrate scopes. Moreover, the indenones obtained in this procedure can be further functionalized to form some more synthetic useful derivatives via an environmental-friendly way.

  DOI：

  10.1021/jo501444g

文献信息

• Rhodium-catalyzed Carbonylative Annulation of 2-Bromobenzylic Alcohols with Internal Alkynes Using Furfural via β-Aryl Elimination
  作者：Takuma Furusawa、Hiroki Tanimoto、Yasuhiro Nishiyama、Tsumoru Morimoto、Kiyomi Kakiuchi

  DOI：10.1246/cl.170249

  日期：2017.7.5

  made in transformations of unstrained benzylic (tert-)alcohols through β-aryl elimination, catalytic carbonylation has not yet been developed extensively because alkoxycarbonylation is probably favored over β-aryl elimination. In this letter, we report on the rhodium(I)-catalyzed carbonylative annulation of α,α-dimethyl-(2-bromoaryl)methanols with internal alkynes using furfural leading to the formation

  尽管通过β-芳基消除在无应变的苄基（叔）醇转化方面取得了重大进展，但催化羰基化尚未得到广泛发展，因为烷氧基羰基化可能比β-芳基消除更受青睐。在这封信中，我们报告了铑（I）催化的α，α-二甲基-（2-溴芳基）甲醇与内部炔烃的羰基化环化，使用糠醛导致茚酮的形成。反应成功的关键是通过糠醛的脱羰及时产生羰基源。
• CuCl-mediated tandem CO insertion and annulation of 1,4-dilithio-1,3-dienes: formation of multiply substituted cyclopentadienones and/or their head-to-head dimers
  作者：Qian Luo、Chao Wang、Wen-Xiong Zhang、Zhenfeng Xi

  DOI：10.1039/b719007g

  日期：——

  Mediated by CuCl, 1,4-dilithio-1,3-dienes reacted with carbon monoxide (CO) to generate multi-substituted cyclopentadienones and/or their head-to-head dimers, via tandem CO insertion and intra/intermolecular cycloaddition of organocopper compounds.

  在氯化铜的介导下，1,4-二硫-1,3-二烯与一氧化碳（CO）反应，通过串联 CO 插入和有机铜化合物的分子内/分子间环加成，生成多取代环戊二烯酮和/或其头对头二聚体。
• Ni-Catalyzed Larock Indenone Annulation with Aliphatic- and Silyl-Substituted Alkynes Supported by Mechanistic Analysis
  作者：Hannah M. Hynds、Holli E. Lemons、Jasmine D. Willis、MarKayla J. Bell、Sydney E. Bottcher、Mei Lin N. Dye、Emily T. Echols、Edward L. Garner、Lauren E. Hutchinson、Caleb M. Phillips、Claudia P. Stephens、Thomas M. Gilbert、Dale J. Wilger

  DOI：10.1021/acs.organomet.2c00016

  日期：2022.3.28
• Efficient Synthesis of Cyclopentadienone Derivatives by the Reaction of Carbon Dioxide with 1,4-Dilithio-1,3-dienes
  作者：Zhenfeng Xi、Qiuling Song

  DOI：10.1021/jo005641r

  日期：2000.12.1

  One-pot reaction of carbon dioxide with 1,4-dilithio-1,3-diene derivatives afforded cyclopentadienone derivatives bearing various substituents in high yields within several minutes.
• CO insertion reaction of zirconacyclopentadienes
  作者：Zhenfeng Xi、Hong-Tao Fan、Shizue Mito、Tamotsu Takahashi

  DOI：10.1016/s0022-328x(03)00711-3

  日期：2003.10

  Alkyl-substituted zirconacyclopentadienes reacted with CO directly at room temperature to give cyclopentenone derivatives as a mixture of cis and trans isomers after hydrolysis. Cyclopentadienones were not obtained. In the case of zirconaindene, both of indanones and indenones were obtained after hydrolysis. Treatment of unsymmetrical zirconacyclopentadienes prepared from diphenylacetylene and 4-octyne with CO at room temperature afforded cyclopentenones as a mixture of positional isomers of the double bond. (C) 2003 Elsevier B.V. All rights reserved.