1,6-bis(tert-butyldimethylsilyl)-1,3,5-hexatriyne | 134816-75-4

• 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-butyldimethylsilyl)-1,3,5-hexatriyne
• 英文别名: Tert-butyl-[6-[tert-butyl(dimethyl)silyl]hexa-1,3,5-triynyl]-dimethylsilane
• CAS: 134816-75-4
• 化学式: C₁₈H₃₀Si₂
• 分子量: 302.607
• InChiKey: PNOHHJWGZCZFRS-UHFFFAOYSA-N

物化性质

• 熔点：
  147-149 °C
• 沸点：
  327.5±25.0 °C(predicted)
• 密度：
  0.871±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.09
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  (叔丁基二甲基)乙炔 在 N-溴代丁二酰亚胺(NBS) 、 盐酸羟胺 、 silver nitrate 、 正丁胺 、 copper(l) chloride 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 2.0h， 生成 1,6-bis(tert-butyldimethylsilyl)-1,3,5-hexatriyne
  参考文献：
  名称：

  Contingency and Serendipity in the Reactions of Fischer Carbene Complexes with Conjugated Triynes

  摘要：

  The first examples of reactions of Fischer carbene complexes with triynes are reported. The regioselectivity of the reaction of the two different alkyne functions in the symmetrical triyne depends on the nature of the substituent of the triyne. Bis-silyl-substituted triynes react at the central alkyne unit, whereas bis-aryl- and bis-alkyl-substituted triynes react at the end alkyne unit. The reaction of a Fischer carbene complex with a phenyl substituent also reacts with a bis-silyl-substituted triyne at the central alkyne unit but gives a furan product rather than the normal phenol product. It was also demonstrated that all three of the alkyne units in conjugated triynes could react in turn with a Fischer carbene complex to give access to trisquinones.

  DOI：

  10.1021/ja049836i

文献信息

• [2 + 2] Cycloreversion of [4.3.2]Propella-1,3,11-trienes:  An Approach to Cyclo[<i>n</i>]carbons from Propellane-Annelated Dehydro[<i>n</i>]annulenes
  作者：Yoshito Tobe、Toshihiko Fujii、Hideki Matsumoto、Kunihiro Tsumuraya、Daisuke Noguchi、Nobuko Nakagawa、Motohiro Sonoda、Koichiro Naemura、Yohji Achiba、Tomonari Wakabayashi

  DOI：10.1021/ja993314z

  日期：2000.3.1

  Next, dehydro[12]-, [16]-, [18]-, [20]-, and [24]annulene derivatives annelated by the [4.3.2]propellatriene units were prepared as precursors to the corresponding cyclo[n]carbons, a monocyclic form of carbon clusters. Laser-desorption mass spectra of the dehydroannulenes exhibited, in the negative mode, peaks due to the corresponding cyclo[n]carbon anions (n = 12, 16, 18, 20, and 24) formed by successive

  作为一种从稳定的前体生成具有高反应性聚炔单元的全碳分子的方法，开发了 [4.3.2]propella-1,3,11-triene 衍生物的 [2 + 2] 环回复。为了测试该方法的效率，该反应首先应用于简单的二乙炔基和二丁二炔基取代的丙炔三烯，它们分别在紫外线照射下产生线性己三炔和十戊炔衍生物。接下来，制备了由 [4.3.2] 丙炔三烯单元退火的脱氢 [12]-、[16]-、[18]-、[20]- 和 [24] 环烯衍生物作为相应环 [n] 的前体碳，碳簇的单环形式。脱氢环烯的激光解吸质谱在负模式下表现出由于相应的环 [n] 碳阴离子（n = 12, 16, 18, 20, 和 24) 由芳香族茚满碎片的连续损失形成。脱氢[16]环烯和脱氢[18]环烯衍生物的溶液光解通过[2+2]环还原反应形成反应性聚炔中间体...
• Photochemical Method for Generation of Linear Polyynes: [2 + 2] Cycloreversion of [4.3.2]Propellatrienes Extruding Indan
  作者：Yoshito Tobe、Toshihiko Fujii、Koichiro Naemura

  DOI：10.1021/jo00085a003

  日期：1994.3

  Photolysis of trienediynes 1a and 1b and trienetetrayne 1c having a [4.3.2]propellane framework yielded the respective linear polyynes 2a-c in good efficiency through [2 + 2] cycloreversion, extruding indan (3).
• 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.
• Contingency and Serendipity in the Reactions of Fischer Carbene Complexes with Conjugated Triynes
  作者：May Xiao-Wu Jiang、Manish Rawat、William D. Wulff

  DOI：10.1021/ja049836i

  日期：2004.5.1

  The first examples of reactions of Fischer carbene complexes with triynes are reported. The regioselectivity of the reaction of the two different alkyne functions in the symmetrical triyne depends on the nature of the substituent of the triyne. Bis-silyl-substituted triynes react at the central alkyne unit, whereas bis-aryl- and bis-alkyl-substituted triynes react at the end alkyne unit. The reaction of a Fischer carbene complex with a phenyl substituent also reacts with a bis-silyl-substituted triyne at the central alkyne unit but gives a furan product rather than the normal phenol product. It was also demonstrated that all three of the alkyne units in conjugated triynes could react in turn with a Fischer carbene complex to give access to trisquinones.