(E)-1-methyl-2-(1-(trimethylsilyl)prop-1-en-2-yl)-1H-indole-3-carbaldehyde | 351055-32-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (E)-1-methyl-2-(1-(trimethylsilyl)prop-1-en-2-yl)-1H-indole-3-carbaldehyde
• 英文别名: 1-methyl-2-[(E)-1-trimethylsilylprop-1-en-2-yl]indole-3-carbaldehyde
• CAS: 351055-32-8
• 化学式: C₁₆H₂₁NOSi
• 分子量: 271.434
• InChiKey: WTEDYLKUOYHDJW-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  在 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以32 mg的产率得到(E)-1-methyl-2-(1-(trimethylsilyl)prop-1-en-2-yl)-1H-indole-3-carbaldehyde
  参考文献：
  名称：

  Iron-Catalyzed Directed C2-Alkylation and Alkenylation of Indole with Vinylarenes and Alkynes

  摘要：

  An iron-N-heterocyclic carbene catalyst generated from an iron(III) salt, an imidazolinium salt, and a Grignard reagent promotes alkylation and alkenylation reactions at the indole C2-position with vinylarenes and internal alkynes, respectively, via imine-directed C-H activation. The former reaction affords 1,1-diarylalkane derivatives with exclusive regioselectivity. Deuterium-labeling experiments suggest that these reactions involve oxidative addition of the C-H bond to the iron center, insertion of the unsaturated bond into the Fe-H bond, and C-C reductive elimination.

  DOI：

  10.1021/ol503395g

文献信息

• Cobalt-catalyzed ortho-alkenylation of aromatic aldimines via chelation-assisted C–H bond activation
  作者：Takeshi Yamakawa、Naohiko Yoshikai

  DOI：10.1016/j.tet.2013.02.092

  日期：2013.6

  An ortho-alkenylation reaction of an aromatic aldimine with an internal alkyne is efficiently promoted by a cobalt catalyst generated from CoBr2, triarylphosphine, and iPrMgBr. The reaction takes place under mild room-temperature conditions to afford, upon acidic hydrolysis, a variety of ortho-alkenylated aromatic aldehydes in moderate to excellent yields. The neighboring formyl and alkenyl groups

  由CoBr 2，三芳基膦和i PrMgBr生成的钴催化剂可有效地促进芳族醛亚胺与内部炔烃的邻链烯基化反应。该反应在温和的室温条件下进行，以酸性水解后以中等至极好的收率得到各种邻链烯基化的芳族醛。产物中相邻的甲酰基和烯基可用作合成结构，以方便地构造茚和萘碳环。