1-(tert-Butyl-dimethyl-silanyl)-4-trimethylsilanyl-buta-1,3-diyne | 920282-72-0

• 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-(tert-Butyl-dimethyl-silanyl)-4-trimethylsilanyl-buta-1,3-diyne
• 英文别名: tert-Butyl(dimethyl)[4-(trimethylsilyl)buta-1,3-diyn-1-yl]silane；tert-butyl-dimethyl-(4-trimethylsilylbuta-1,3-diynyl)silane
• CAS: 920282-72-0
• 化学式: C₁₃H₂₄Si₂
• 分子量: 236.505
• InChiKey: WIHCKPSVSUAVFY-UHFFFAOYSA-N

物化性质

• 沸点：
  248.7±23.0 °C(Predicted)
• 密度：
  0.840±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-(tert-Butyl-dimethyl-silanyl)-4-trimethylsilanyl-buta-1,3-diyne 在 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 1-(tert-butyldimethylsilyl)butadiyne
  参考文献：
  名称：

  Regioselective Trapping of Terminal Di-, Tri-, and Tetraynes with Benzyl Azide

  摘要：

  The reaction of benzyl azide with terminal di-, tri-, and tetraynes appended with a range of functional groups has been explored. Standard reaction conditions for BnN3 catalyzed by CuSO(4)(.)5H(2)O gave alkynyl, butadiynyl, and hexatriynyl triazoles in moderate to good yields. The reaction proceeds regioselectively as determined by the X-ray crystallographic analysis of three derivatives (1c, 1d, and 3c), and no evidence of multiple azide addition to the polyyne framework is observed.

  DOI：

  10.1021/ol062522a
• 作为产物：
  描述：

  3-(tert-butyldimethylsilyl)-2-propynal 在 三苯基膦 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.08h， 生成 1-(tert-Butyl-dimethyl-silanyl)-4-trimethylsilanyl-buta-1,3-diyne
  参考文献：
  名称：

  Regioselective Trapping of Terminal Di-, Tri-, and Tetraynes with Benzyl Azide

  摘要：

  The reaction of benzyl azide with terminal di-, tri-, and tetraynes appended with a range of functional groups has been explored. Standard reaction conditions for BnN3 catalyzed by CuSO(4)(.)5H(2)O gave alkynyl, butadiynyl, and hexatriynyl triazoles in moderate to good yields. The reaction proceeds regioselectively as determined by the X-ray crystallographic analysis of three derivatives (1c, 1d, and 3c), and no evidence of multiple azide addition to the polyyne framework is observed.

  DOI：

  10.1021/ol062522a

文献信息

• Thieme Chemistry Journal Awardees - Where Are They Now? Pentafluorophenyl End-Capped Polyynes as Supramolecular Building Blocks
  作者：Rik Tykwinski、Jamie Kendall、Robert McDonald

  DOI：10.1055/s-0029-1217706

  日期：2009.8

  The synthesis of pentafluorophenyl end-capped polyynes up to an octayne has been developed based on the use of a Fritsch-Buttenberg-Wiechell rearrangement as the key step. UV/ Vis spectroscopic analysis shows little change in the electronic nature of these structures as phenyl is formally replaced by pentafluorophenyl. The ability of pentafluorophenyl polyynes to function as supramolecular building

  基于使用 Fritsch-Buttenberg-Wiechell 重排作为关键步骤，开发了五氟苯基封端的聚炔合成至辛炔。紫外/可见光谱分析显示这些结构的电子性质几乎没有变化，因为苯基在形式上被五氟苯基取代。五氟苯基聚炔在主客体系统中作为超分子结构单元的能力通过在三炔 5 和十氟甲苯胺之间形成包合物来证明。
• Reactions of Terminal Polyynes with Benzyl Azide
  作者：Thanh Luu、Boris J. Medos、Erin R. Graham、Danielle M. Vallee、Robert McDonald、Michael J. Ferguson、Rik R. Tykwinski

  DOI：10.1021/jo101870y

  日期：2010.12.17

  Terminal di-, tri-, tetra-, and pentaynes substituted with a variety of functional groups react with benzyl azide in the presence of CuSO4 center dot 5H(2)O and ascorbic acid to give derivatives of 4-ethynyl-, 4-butadiynyl-, 4-hexatriynyl-, and 4-octatetraynyl-,2,3-triazoles in moderate to good yields. These reactions appear to proceed regioselectively, and functionalization occurs exclusively at the terminal alkyne moiety. As well, no evidence of multiple azide additions to the polyyne framework is observed. X-ray crystallographic analysis of nine derivatives is used to document the regioselectivity of the reaction as well as outline structural characteristics of the 1,2,3-triazole products.