1,4-bis<4-<(tert-butyldimethylsilyl)ethynyl>-1,2-dioxo-3-cyclobuten-3-yl>-1,3-butadiyne | 134816-73-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 1,4-bis<4-<(tert-butyldimethylsilyl)ethynyl>-1,2-dioxo-3-cyclobuten-3-yl>-1,3-butadiyne
• 英文别名: 3-[2-[Tert-butyl(dimethyl)silyl]ethynyl]-4-[4-[2-[2-[tert-butyl(dimethyl)silyl]ethynyl]-3,4-dioxocyclobuten-1-yl]buta-1,3-diynyl]cyclobut-3-ene-1,2-dione；3-[2-[tert-butyl(dimethyl)silyl]ethynyl]-4-[4-[2-[2-[tert-butyl(dimethyl)silyl]ethynyl]-3,4-dioxocyclobuten-1-yl]buta-1,3-diynyl]cyclobut-3-ene-1,2-dione
• CAS: 134816-73-2
• 化学式: C₂₈H₃₀O₄Si₂
• 分子量: 486.715
• InChiKey: KKLYLMFILWALAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.08
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  68.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-bis<4-<(tert-butyldimethylsilyl)ethynyl>-1,2-dioxo-3-cyclobuten-3-yl>-1,3-butadiyne 以 苯 为溶剂， 以31%的产率得到1,12-bis(tert-butyldimethylsilyl)-1,3,5,7,9,11-dodecahexayne
  参考文献：
  名称：

  Solution-spray flash vacuum pyrolysis: a new method for the synthesis of linear poliynes with odd numbers of C.tplbond.C bonds from substituted 3,4-dialkynyl-3-cyclobutene-1,2-diones

  摘要：

  We report a new method for the preparation of a wide range of linear poliynes, 1a-1i, with an odd number of C = C bonds. This method is based on solution-spray flash vacuum pyrolysis (SS-FVP) of the readily available 3,4-dialkynyl-3-cyclobutene-1,2-diones 3a-3i. It allows the synthesis of multigram quantities of a series of hexatriynes and decapentaynes from poorly volatile and thermally unstable precursors that cannot be subjected to conventional flash vacuum pyrolysis. Yields of the linear poliynes range from 42 to 99%. Similarly, the dodecahexayne 1j was obtained in 31% yield by SS-FVP of the bis(3-cyclobutene-1,2-dione) 3j. The synthesis of the new 3,4-dialkynyl-3-cyclobutene-1,2-diones 3h-3j via the ketals 7, 10, and 13 is reported. The X-ray crystal structure of 1,10-diphenyl-1,3,5,7,9-decapentayne (1c) was solved, and the crystal packing structure provides valuable information to explain the thermal polymerization behavior observed for this compound in the crystalline state.

  DOI：

  10.1021/ja00018a035
• 作为产物：
  描述：

  1,4-bis<12-<(tert-butyldimethylsilyl)ethynyl>-1,4,7,10-tetraoxadispiro<4.0.4.2>-11-dodecen-11-yl>-1,3-butadiyne 在 硫酸 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以90%的产率得到1,4-bis<4-<(tert-butyldimethylsilyl)ethynyl>-1,2-dioxo-3-cyclobuten-3-yl>-1,3-butadiyne
  参考文献：
  名称：

  Solution-spray flash vacuum pyrolysis: a new method for the synthesis of linear poliynes with odd numbers of C.tplbond.C bonds from substituted 3,4-dialkynyl-3-cyclobutene-1,2-diones

  摘要：

  We report a new method for the preparation of a wide range of linear poliynes, 1a-1i, with an odd number of C = C bonds. This method is based on solution-spray flash vacuum pyrolysis (SS-FVP) of the readily available 3,4-dialkynyl-3-cyclobutene-1,2-diones 3a-3i. It allows the synthesis of multigram quantities of a series of hexatriynes and decapentaynes from poorly volatile and thermally unstable precursors that cannot be subjected to conventional flash vacuum pyrolysis. Yields of the linear poliynes range from 42 to 99%. Similarly, the dodecahexayne 1j was obtained in 31% yield by SS-FVP of the bis(3-cyclobutene-1,2-dione) 3j. The synthesis of the new 3,4-dialkynyl-3-cyclobutene-1,2-diones 3h-3j via the ketals 7, 10, and 13 is reported. The X-ray crystal structure of 1,10-diphenyl-1,3,5,7,9-decapentayne (1c) was solved, and the crystal packing structure provides valuable information to explain the thermal polymerization behavior observed for this compound in the crystalline state.

  DOI：

  10.1021/ja00018a035

文献信息

• Solution-spray flash vacuum pyrolysis: a new method for the synthesis of linear poliynes with odd numbers of C.tplbond.C bonds from substituted 3,4-dialkynyl-3-cyclobutene-1,2-diones
  作者：Yves Rubin、Sophia S. Lin、Carolyn B. Knobler、John Anthony、Armen M. Boldi、Francois Diederich

  DOI：10.1021/ja00018a035

  日期：1991.8

  We report a new method for the preparation of a wide range of linear poliynes, 1a-1i, with an odd number of C = C bonds. This method is based on solution-spray flash vacuum pyrolysis (SS-FVP) of the readily available 3,4-dialkynyl-3-cyclobutene-1,2-diones 3a-3i. It allows the synthesis of multigram quantities of a series of hexatriynes and decapentaynes from poorly volatile and thermally unstable precursors that cannot be subjected to conventional flash vacuum pyrolysis. Yields of the linear poliynes range from 42 to 99%. Similarly, the dodecahexayne 1j was obtained in 31% yield by SS-FVP of the bis(3-cyclobutene-1,2-dione) 3j. The synthesis of the new 3,4-dialkynyl-3-cyclobutene-1,2-diones 3h-3j via the ketals 7, 10, and 13 is reported. The X-ray crystal structure of 1,10-diphenyl-1,3,5,7,9-decapentayne (1c) was solved, and the crystal packing structure provides valuable information to explain the thermal polymerization behavior observed for this compound in the crystalline state.