2,2-dimethyl-7-(triisopropylsilyl)hepta-4,6-diyn-3-one | 1616860-10-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-dimethyl-7-(triisopropylsilyl)hepta-4,6-diyn-3-one
• CAS: 1616860-10-6
• 化学式: C₁₈H₃₀OSi
• 分子量: 290.521
• InChiKey: MOZUKWFECOIMFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.83
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-7-(triisopropylsilyl)hepta-4,6-diyn-3-one 在 肼 作用下， 以 乙腈 为溶剂， 以62%的产率得到3-(tert-butyl)-5-((triisopropylsilyl)ethynyl)-1H-pyrazole
  参考文献：
  名称：

  Gold-Catalyzed 1,3-Transposition of Ynones

  摘要：

  An efficient, regioselective gold-catalyzed 1,3-transposition reaction of ynones and diynones has been developed. It was found that stereoelectronic (interrupted conjugation) and electronic (extended conjugation) factors could efficiently govern the regioselectivity of this thermodynamically controlled transformation. The produced conjugated diynones were efficiently transformed into diverse alkyne-substituted five- and six-membered heterocycles.

  DOI：

  10.1021/ja504892c
• 作为产物：
  描述：

  6,6-dimethyl-1-(triisopropylsilyl)hepta-1,4-diyn-3-one 在 silver tetrafluoroborate 、 氯[三(2,4-二叔丁基苯基)亚磷酸]金 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以83%的产率得到2,2-dimethyl-7-(triisopropylsilyl)hepta-4,6-diyn-3-one
  参考文献：
  名称：

  Gold-Catalyzed 1,3-Transposition of Ynones

  摘要：

  An efficient, regioselective gold-catalyzed 1,3-transposition reaction of ynones and diynones has been developed. It was found that stereoelectronic (interrupted conjugation) and electronic (extended conjugation) factors could efficiently govern the regioselectivity of this thermodynamically controlled transformation. The produced conjugated diynones were efficiently transformed into diverse alkyne-substituted five- and six-membered heterocycles.

  DOI：

  10.1021/ja504892c

文献信息

• De Novo Ring-Forming Consecutive Four-Component Syntheses of 4-Pyrazolyl-1,2,3-triazoles from (Triisopropylsilyl)butadiyne as a C4 Building Block
  作者：Patrik Niesobski、Fabian Klukas、Henning Berens、Gamall Makhloufi、Christoph Janiak、Thomas J. J. Müller

  DOI：10.1021/acs.joc.8b00430

  日期：2018.4.20

  4-Pyrazolyl-1,2,3-triazoles can be readily synthesized in a one-pot fashion and moderate yield by employing a consecutive four-component process consisting of a sequentially Pd-Cu-catalyzed alkynylation-cyclocondensation-desilylation-CuAAC process. Most distinctly, (triisopropylsilyl)butadiyne is employed as a four-carbon building block in this one-pot de novo formation of both heterocyclic moieties.