1-(tert-butyldimethylsilyl)butadiyne | 113860-45-0

• 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-butyldimethylsilyl)butadiyne
• 英文别名: buta-1,3-diynyl-tert-butyl-dimethylsilane
• CAS: 113860-45-0
• 化学式: C₁₀H₁₆Si
• 分子量: 164.323
• InChiKey: DCWDBMFPEMAPCY-UHFFFAOYSA-N

物化性质

• 沸点：
  186.4±9.0 °C(Predicted)
• 密度：
  0.836±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  11.0
• 可旋转键数：
  0.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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-(tert-butyldimethylsilyl)butadiyne 在 aluminum (III) chloride 、 氯化亚砜 、 甲基锂 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 1-tert-butyldimethylsilyl-5-dibromomethylene-7-pentafluorophenyl-1,3,6-heptatriyne
  参考文献：
  名称：

  Thieme Chemistry Journal 获奖者 - 他们现在在哪里？五氟苯基封端聚炔作为超分子结构单元

  摘要：

  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。

  DOI：

  10.1055/s-0029-1217706
• 作为产物：
  描述：

  3-(tert-butyldimethylsilyl)-2-propynal 在 potassium carbonate 、 三苯基膦 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.08h， 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

文献信息

• Selectivity for Alkynyl or Allenyl Imidamides and Imidates in Copper-Catalyzed Reactions of Terminal 1,3-Diynes and Azides
  作者：Sourav Ghorai、Daesung Lee

  DOI：10.1021/acs.orglett.0c03861

  日期：2021.2.5

  Copper-catalyzed reactions of terminal 1,3-diynes with electron-deficient azides to generate either 3-alkynyl or 2,3-dienyl imidamides and imidates are described. The selectivity depends on the diyne substituents and the nucleophile that reacts with the ketenimide intermediate generated from the corresponding triazole precursor. Reactions of 1,3-diynes containing a propargylic acetate afford [3]cumulenyl

  描述了末端的1，3-二炔与缺电子的叠氮化物的铜催化反应以生成3-炔基或2，3-二烯基亚酰胺和酰亚胺。选择性取决于二炔取代基和与相应三唑前体生成的酮丁酰亚胺中间体反应的亲核试剂。含有炔丙基乙酸酯的1,3-二炔反应生成[3]枯烯基亚酰胺，而使用甲醇作为捕集剂的反应选择性生成2,3-二烯基酰亚胺。从含有均丙基羟基或胺取代基的1，3-二炔获得五元杂环。
• Alkynylcyanation of alkynes and dienes catalyzed by nickel
  作者：Yasuhiro Hirata、Masaaki Tanaka、Akira Yada、Yoshiaki Nakao、Tamejiro Hiyama

  DOI：10.1016/j.tet.2009.03.079

  日期：2009.6

  Alkynyl cyanides are found to add across alkynes and 1,2-dienes in the presence of a catalyst prepared in situ from Ni(cod)(2), xantphos, and BPh3. A range of functionalized conjugated cis-enynes are obtained with high regioselectivity. The addition reaction across norbornadiene proceeds in the absence of BPh3 to give exo-cis adduct exclusively. A stoichiometric reaction of ail alkynyl cyanide, Ni(cod)2, xantphos, and BPh3 gives trans-(xantphos)Ni(CNBPh3)(C CSiMe(2)t-Bu), which is suggested to be a plausible reaction intermediate of the alkynylcyanation reaction. (C) 2009 Elsevier Ltd. All rights reserved.
• 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.
• Yamaguchi, Masahiko; Torisu, Kazuhiko; Hiraki, Ken-ichi, Chemistry Letters, 1990, # 12, p. 2221 - 2222
  作者：Yamaguchi, Masahiko、Torisu, Kazuhiko、Hiraki, Ken-ichi、Minami, Toru

  DOI：——

  日期：——
• SHIM, SANG CHUL;LEE, TAE SUK, J. ORG. CHEM., 53,(1988) N 11, 2410-2413
  作者：SHIM, SANG CHUL、LEE, TAE SUK

  DOI：——

  日期：——