(Z)-1-(tert-butyldimethylsilyl)-1-dodecene | 183290-32-6

• 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: (Z)-1-(tert-butyldimethylsilyl)-1-dodecene
• 英文别名: (Z)-1-(t-butyldimethylsilyl)-1-dodecene；tert-butyl-[(Z)-dodec-1-enyl]-dimethylsilane
• CAS: 183290-32-6
• 化学式: C₁₈H₃₈Si
• 分子量: 282.585
• InChiKey: YXNMBTVKAGQABU-MSUUIHNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.12
• 重原子数：
  19
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  苯甲醛 、 (Z)-1-(tert-butyldimethylsilyl)-1-dodecene 在 platinum(II) chloride 、 lithium iodide 作用下， 以 1,2-二氯乙烷 为溶剂， 以29%的产率得到2-[(t-butyldimethylsiloxy)(phenyl)methyl]-1-dodecene
  参考文献：
  名称：

  Platinum-Catalyzed Nucleophilic Addition of Vinylsilanes at the β-Position

  摘要：

  In the presence of catalytic amounts of PtCl(2) and metal iodides, beta-substituted vinylsilanes reacted with aldehydes at the beta-position to give allyl silyl ethers. The Pt-catalyzed addition to aromatic aldehydes proceeded efficiently in the presence of Lil. The combined use of PtCl(2) and Mnl(2) was found to be effective in addition to aliphatic aldehydes.

  DOI：

  10.1021/ol902060r
• 作为产物：
  描述：

  Tert-butyl-dodec-1-ynyl-dimethylsilane 在 二异丁基氢化铝 作用下， 以 乙醚 、 正己烷 为溶剂， 生成 (Z)-1-(tert-butyldimethylsilyl)-1-dodecene
  参考文献：
  名称：

  Platinum-Catalyzed Nucleophilic Addition of Vinylsilanes at the β-Position

  摘要：

  In the presence of catalytic amounts of PtCl(2) and metal iodides, beta-substituted vinylsilanes reacted with aldehydes at the beta-position to give allyl silyl ethers. The Pt-catalyzed addition to aromatic aldehydes proceeded efficiently in the presence of Lil. The combined use of PtCl(2) and Mnl(2) was found to be effective in addition to aliphatic aldehydes.

  DOI：

  10.1021/ol902060r

文献信息

• Lewis Acid Catalyzed Highly Regio- and Stereocontrolled <i>Trans</i>-Hydrosilylation of Alkynes and Allenes
  作者：Tomoko Sudo、Naoki Asao、Vladimir Gevorgyan、Yoshinori Yamamoto

  DOI：10.1021/jo9824293

  日期：1999.4.1

  Lewis acids such as AlCl3 or EtAlCl2 dramatically catalyzed the hydrosilylation of alkynes 1 with trialkylsilanes to produce the corresponding cis-vinylsilanes 2 in a regio- and trans-stereoselective manner. For example, the hydrosilylation of 1-dodecyne la with triethylsilane in the presence of 0.2 equiv of AlCl3 gave cis-1-(triethylsilyl)-1-dodecene in 93% yield. Other alkyl- and phenyl-substituted terminal and internal acetylenes also underwent trans-hydrosilylation very smoothly. In the case of alkoxy- or silyloxy-substituted acetylenes, the use of 1.2 equiv of AlCl3 or EtAlCl2 was essential to obtain the corresponding trans-hydrosilylation products in high yields. Moreover, AlCl3 catalyzed the hydrosilylation of aromatic allenes 11, producing the alkenylsilanes 12 with high regio- and stereoselectivities in moderate to high chemical yields. Not only the simple monosubstituted, but also the disubstituted and trisubstituted allenes, underwent the hydrosilylation reaction smoothly, serving as a useful tool for the synthesis of differently substituted vinylsilanes which are not easily available through the previously known methodologies. The mechanisms for these catalytic reactions of alkynes and allenes are proposed.
• Lewis Acid-Catalyzed <i>trans</i>-Hydrosilylation of Alkynes
  作者：Naoki Asao、Tomoko Sudo、Yoshinori Yamamoto

  DOI：10.1021/jo961508g

  日期：1996.1.1
• Platinum-Catalyzed Nucleophilic Addition of Vinylsilanes at the β-Position
  作者：Katsukiyo Miura、Gen Inoue、Hisashi Sasagawa、Hidenori Kinoshita、Junji Ichikawa、Akira Hosomi

  DOI：10.1021/ol902060r

  日期：2009.11.5

  In the presence of catalytic amounts of PtCl(2) and metal iodides, beta-substituted vinylsilanes reacted with aldehydes at the beta-position to give allyl silyl ethers. The Pt-catalyzed addition to aromatic aldehydes proceeded efficiently in the presence of Lil. The combined use of PtCl(2) and Mnl(2) was found to be effective in addition to aliphatic aldehydes.