(3-(pent-3-ynyloxy)prop-1-ynyl)benzene | 1315322-23-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3-(pent-3-ynyloxy)prop-1-ynyl)benzene
• 英文别名: 3-Pent-3-ynoxyprop-1-ynylbenzene；3-pent-3-ynoxyprop-1-ynylbenzene
• CAS: 1315322-23-6
• 化学式: C₁₄H₁₄O
• 分子量: 198.265
• InChiKey: JIFYJNCBISLPRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3-(pent-3-ynyloxy)prop-1-ynyl)benzene 在 methyl(triphenylphosphine)gold(I) 、 水 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 3-甲氧基-1-苯基丙烷-1-酮
  参考文献：
  名称：

  Indium(III)-Catalyzed Hydrative Cyclization of 1,7-Diynyl Ethers

  摘要：

  A new hydrative cyclization of 1,7- and 1,8-diynyl ethers is reported. Using catalytic InI(3) and p-TSA as a cocatalyst, several 2,2-disubstituted tetrahydrofurans with exocyclic enone appendages were prepared. Reaction optimization and scope, mechanistic insight, and further transformation to a C-nucleoside analog are presented.

  DOI：

  10.1021/ol201624b
• 作为产物：
  描述：

  碘苯 、 5-prop-2-ynyloxy-pent-2-yne 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 22.0h， 以76%的产率得到(3-(pent-3-ynyloxy)prop-1-ynyl)benzene
  参考文献：
  名称：

  Indium(III)-Catalyzed Hydrative Cyclization of 1,7-Diynyl Ethers

  摘要：

  A new hydrative cyclization of 1,7- and 1,8-diynyl ethers is reported. Using catalytic InI(3) and p-TSA as a cocatalyst, several 2,2-disubstituted tetrahydrofurans with exocyclic enone appendages were prepared. Reaction optimization and scope, mechanistic insight, and further transformation to a C-nucleoside analog are presented.

  DOI：

  10.1021/ol201624b

文献信息

• Synthesis of Cyclopenta[<i>c</i>]quinolines by Palladium-Catalyzed Cyclization of 3-Bromoindoles with Internal Alkynes via Spirocyclic Cyclopentadiene Intermediates
  作者：Biao Guo、Jiaying Lv、Le Lu、Ruimao Hua

  DOI：10.1021/acs.joc.3c00716

  日期：2023.7.7

  involving a sequential double alkyne insertion into the carbon–palladium bond and dearomatization of indole. The present studies have developed a novel ring-expansion reaction of the pyrrole ring to pyridine via one carbon insertion into the C2–C3 bond of indoles and provided a simple and distinct route for the construction of tricyclic fused-quinoline derivatives that are not easy to access with conventional

  描述了一种在钯存在下通过 3-溴吲哚与内部炔烃环化构建环戊[ c ]喹啉环的新方法。环戊烷的形成[ c]喹啉环是由螺环环戊二烯中间体的双[1,5]碳σ重排提出的，该中间体是通过3-溴吲哚与内部炔烃的环化原位生成的，涉及连续的双炔插入碳-钯键和吲哚的脱芳构化。目前的研究开发了一种通过在吲哚的C2-C3键上插入一个碳将吡咯环扩环为吡啶的新型反应，并为构建不易合成的三环稠合喹啉衍生物提供了一种简单而独特的路线。通过常规方法访问。
• Indium(III)-Catalyzed Hydrative Cyclization of 1,7-Diynyl Ethers
  作者：Amanda L. Gibeau、John K. Snyder

  DOI：10.1021/ol201624b

  日期：2011.8.19

  A new hydrative cyclization of 1,7- and 1,8-diynyl ethers is reported. Using catalytic InI(3) and p-TSA as a cocatalyst, several 2,2-disubstituted tetrahydrofurans with exocyclic enone appendages were prepared. Reaction optimization and scope, mechanistic insight, and further transformation to a C-nucleoside analog are presented.