1,6-bis(tert-butyldiphenylsilyl)-1,3,5-hexatriyne | 134816-79-8

• 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: 1,6-bis(tert-butyldiphenylsilyl)-1,3,5-hexatriyne
• 英文别名: 1,6-bis(t-butyldiphenylsilyl)-1,3,5-hexatriyne；tert-butyl-[6-[tert-butyl(diphenyl)silyl]hexa-1,3,5-triynyl]-diphenylsilane
• CAS: 134816-79-8
• 化学式: C₃₈H₃₈Si₂
• 分子量: 550.891
• InChiKey: DYNDZFSAZMDWMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  40.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  1,6-bis(tert-butyldiphenylsilyl)-1,3,5-hexatriyne 在 六甲基磷酰三胺 、 lithium phenylacetylide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以57%的产率得到1-(t-butyldiphenylsilyl)-1,3,5-hexatriyne
  参考文献：
  名称：

  Synthesis and Reactions of Monosilylated 1,3,5-Hexatriyne and 1,3,5,7-Octatetrayne. Total Synthesis of Caryoynencins

  摘要：

  5-hexatriyne 与石碳酸苯乙炔的反应分别产生了不稳定的 1-(t-丁基二苯基硅烷基)-1,3,5,7-辛四炔和 1-(t-丁基二苯基硅烷基)-1,3,5-hexatriyne。在石化过程中，末端乙炔与醛类和酮类发生反应，产生多炔醇，产量很高。该反应被应用于合成多炔抗生素--卡里诺霉素。在掺杂了 SO3 的 ITO 涂层玻璃板上聚合末端的辛四炔，可得到一层薄膜，其导电率为 10-4 S cm-1。

  DOI：

  10.1246/bcsj.67.1717
• 作为产物：
  描述：

  1,6-bis(trimethylsilyl)hexa-1,3,5-triyne 、 叔丁基二苯基氯硅烷 在 甲基锂 、 lithium bromide 作用下， 生成 1,6-bis(tert-butyldiphenylsilyl)-1,3,5-hexatriyne
  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

• Synthesis and Reactions of Monosilylated 1,3,5-Hexatriyne and 1,3,5,7-Octatetrayne. Total Synthesis of Caryoynencins
  作者：Masahiko Yamaguchi、Hyeon-Joo Park、Masahiro Hirama、Kazuhiko Torisu、Shigeo Nakamura、Toru Minami、Hiroshi Nishihara、Tetsuo Hiraoka

  DOI：10.1246/bcsj.67.1717

  日期：1994.6

  Selective monodesilylation of 1,8-bis(t-butyldiphenylsilyl)-1,3,5,7-octatetrayne and 1,6-bis(t-butyldiphenylsilyl)-1,3,5-hexatriyne with lithiated phenylacetylene gave unstable 1-(t-butyldiphenylsilyl)-1,3,5,7-octatetrayne and 1-(t-butyldiphenylsilyl)-1,3,5-hexatriyne, respectively. The terminal acetylenes on lithiation added to aldehydes and a ketone giving polyynols in high yields. The reaction was applied to the synthesis of polyyne antibiotics, caryoynencins. Polymerization of the terminal octatetrayne on an ITO-coated glass plate gave a film, which showed conductivity of 10−4 S cm−1 when doped with SO3.

  5-hexatriyne 与石碳酸苯乙炔的反应分别产生了不稳定的 1-(t-丁基二苯基硅烷基)-1,3,5,7-辛四炔和 1-(t-丁基二苯基硅烷基)-1,3,5-hexatriyne。在石化过程中，末端乙炔与醛类和酮类发生反应，产生多炔醇，产量很高。该反应被应用于合成多炔抗生素--卡里诺霉素。在掺杂了 SO3 的 ITO 涂层玻璃板上聚合末端的辛四炔，可得到一层薄膜，其导电率为 10-4 S cm-1。
• 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.