1-trimethylsilylquinolinium iodide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-trimethylsilylquinolinium iodide
• 英文别名: 1-(Trimethylsilyl)quinolin-1-ium iodide；trimethyl(quinolin-1-ium-1-yl)silane;iodide
• 化学式: C₁₂H₁₆NSi*I
• 分子量: 329.256
• InChiKey: KPQYFMNRVNKJBS-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.19
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  3.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  喹啉 、 碘代三甲硅烷 以 正己烷 为溶剂， 以99%的产率得到1-trimethylsilylquinolinium iodide
  参考文献：
  名称：

  Total Synthesis of (+)-Lithospermic Acid by Asymmetric Intramolecular Alkylation via Catalytic C−H Bond Activation

  摘要：

  The total synthesis of (+)-lithospermic acid is described. The efficient synthesis features an asymmetric alkylation via C-H bond activation to assemble the dihydrobenzofuran core of the natural product. This was accomplished via a chiral imine-directed C-H bond functionalization and represents the first application of this C-H activation method to natural product synthesis. Furthermore, a challenging deprotection of a late-stage permethylated lithospermic acid was achieved.

  DOI：

  10.1021/ja052680h
• 作为试剂：
  描述：

  2,2-dibromo-1-(3,4-dimethoxyphenyl)ethene 在 哌啶 、 1-trimethylsilylquinolinium iodide 、 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 1-di(2-(5-methylfuryl)phosphanyl)ferrocene 、 正丁基锂 、 [RhCl(coe)2]2 、 4 A molecular sieve 、 sodium methylate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三甲基氢氧化锡 作用下， 以 甲醇 、 正己烷 、 氯仿 、 1,2-二氯乙烷 、 甲苯 、 苯 为溶剂， 反应 129.83h， 生成 紫草酸
  参考文献：
  名称：

  Total Synthesis of (+)-Lithospermic Acid by Asymmetric Intramolecular Alkylation via Catalytic C−H Bond Activation

  摘要：

  The total synthesis of (+)-lithospermic acid is described. The efficient synthesis features an asymmetric alkylation via C-H bond activation to assemble the dihydrobenzofuran core of the natural product. This was accomplished via a chiral imine-directed C-H bond functionalization and represents the first application of this C-H activation method to natural product synthesis. Furthermore, a challenging deprotection of a late-stage permethylated lithospermic acid was achieved.

  DOI：

  10.1021/ja052680h

文献信息

• Total Synthesis of (+)-Lithospermic Acid by Asymmetric Intramolecular Alkylation via Catalytic C−H Bond Activation
  作者：Steven J. O'Malley、Kian L. Tan、Anja Watzke、Robert G. Bergman、Jonathan A. Ellman

  DOI：10.1021/ja052680h

  日期：2005.10.1

  The total synthesis of (+)-lithospermic acid is described. The efficient synthesis features an asymmetric alkylation via C-H bond activation to assemble the dihydrobenzofuran core of the natural product. This was accomplished via a chiral imine-directed C-H bond functionalization and represents the first application of this C-H activation method to natural product synthesis. Furthermore, a challenging deprotection of a late-stage permethylated lithospermic acid was achieved.