1-辛炔基烯丙基二甲基硅烷 | 665012-74-8

• 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
• 中文名称: 1-辛炔基烯丙基二甲基硅烷
• 英文名称: 1-octynyl allyl dimethylsilane
• 英文别名: Dimethyl-oct-1-ynyl-prop-2-enylsilane；dimethyl-oct-1-ynyl-prop-2-enylsilane
• CAS: 665012-74-8
• 化学式: C₁₃H₂₄Si
• 分子量: 208.419
• InChiKey: XMJATYUPNLPEJG-UHFFFAOYSA-N

物化性质

• 沸点：
  241.7±9.0 °C(Predicted)
• 密度：
  0.810±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  14
• 可旋转键数：
  7
• 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-辛炔基烯丙基二甲基硅烷 在 silver hexafluoroantimonate 、 三苯基膦氯金 、 水 作用下， 以 二氯甲烷 为溶剂， 生成 ((Z)-2-Allyl-oct-1-enyl)-dimethyl-silanol 、 2-n-hexyl-1,4-pentadiene
  参考文献：
  名称：

  Gold-Catalyzed Intramolecular Allylation of Silyl Alkynes Induced by Silane Alcoholysis

  摘要：

  The activation of alkynyl allyl silanes with a cationic gold catalyst in the presence of alcohols provides vinyl silanes that contain the allyl group at the beta-position and the alkoxysilyl group in cis-orientation. The bond reorganization process is most consistent with the involvement of a carbocationic intermediate, which undergoes a nucleophilic attack by an alcohol selectively at the silicon center. The cis-vinyl silyl ether products can be further elaborated by ring-closing and cross metathesis to form more substituted 1,4-dienyl silanes.

  DOI：

  10.1021/ja062560p
• 作为产物：
  描述：

  烯丙基二甲基氯硅烷 、 n-己基乙炔基锂 生成 1-辛炔基烯丙基二甲基硅烷
  参考文献：
  名称：

  Gold-Catalyzed Intramolecular Allylation of Silyl Alkynes Induced by Silane Alcoholysis

  摘要：

  The activation of alkynyl allyl silanes with a cationic gold catalyst in the presence of alcohols provides vinyl silanes that contain the allyl group at the beta-position and the alkoxysilyl group in cis-orientation. The bond reorganization process is most consistent with the involvement of a carbocationic intermediate, which undergoes a nucleophilic attack by an alcohol selectively at the silicon center. The cis-vinyl silyl ether products can be further elaborated by ring-closing and cross metathesis to form more substituted 1,4-dienyl silanes.

  DOI：

  10.1021/ja062560p

文献信息

• Four-component coupling reactions of silylacetylenes, allyl carbonates, and trimethylsilyl azide catalyzed by a Pd(0)–Cu(I) bimetallic catalyst. Fully substituted triazole synthesis from seemingly internal alkynes
  作者：Shin Kamijo、Tienan Jin、Yoshinori Yamamoto

  DOI：10.1016/j.tetlet.2003.11.070

  日期：2004.1

  unactivated silylacetylenes, two equivalents of allyl carbonates, and trimethylsilyl azide in the presence of a Pd(0)–Cu(I) bimetallic catalyst. Various trisubstituted 1,2,3-triazoles were obtained in good yields. The reaction most probably proceeds through the [3+2] cycloaddition reaction between the alkynylcopper species and azide followed by the cross-coupling reaction between the vinylcopper intermediate

  通过在Pd（0）-Cu（I）双金属催化剂存在下，未活化的甲硅烷基乙炔，两当量的碳酸烯丙酯和三甲基甲硅烷基叠氮化物的四组分偶联反应，可以合成完全取代的三唑。以良好的产率获得了各种三取代的1,2,3-三唑。该反应最有可能通过炔铜物种与叠氮化物之间的[3 + 2]环加成反应进行，然后是乙烯基铜中间体与π-烯丙基铝络合物之间的交叉偶联反应。