tricarbonyl-[η6-1,3-dimethoxy-5-methyl-2-trimethylsilylbenzene]chromium(0) | 193977-24-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tricarbonyl-[η6-1,3-dimethoxy-5-methyl-2-trimethylsilylbenzene]chromium(0)
• 英文别名: Carbon monoxide;chromium;(2,6-dimethoxy-4-methylphenyl)-trimethylsilane
• CAS: 193977-24-1
• 化学式: C₁₅H₂₀CrO₅Si
• 分子量: 360.402
• InChiKey: XOKRDRUSUUFDOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.44
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  21.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tricarbonyl-[η6-1,3-dimethoxy-5-methyl-2-trimethylsilylbenzene]chromium(0) 、 氯磷酸二乙酯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以59%的产率得到tricarbonyl-[1-(η6-3,5-dimethoxy-4-trimethylsilylphenyl)methyldiethylphosphonate]chromium(0)
  参考文献：
  名称：

  Application of Chromium-Arene Complexes in the Organic Synthesis. Efficient Synthesis of Stilbene Phytoalexins

  摘要：

  Planar chiral eta(6)-arene-Cr(CO)(3) complexes represent highly valuable building blocks for the diastereo- and enantioselective synthesis. Their employment as synthons offer new and unique opportunities for the stereoselective multistep synthesis of complex natural products. The strategy of novel efficient synthesis of stilbene phytoalexins was based on arene chromium chemistry and the chemical and stereochemical effects of the metal unit on the reactivity of complexed arene ligand and stereochemical features of such compounds. Two variants for the construction of the trans-stilbene and diarylethanol framework via facilitated benzylic deprotonation of an eta(6)-benzene-Cr(CO)(3) complex and subsequent coupling with para-anisaidehyde in an aldol-type or a Wittig-Horner reaction were suggested.

  DOI：

  10.1023/b:ruco.0000022800.70211.7d
• 作为产物：
  描述：

  tricarbonyl-[η6-1,3-dimethoxy-2-trimethylsilylbenzene]chromium(0) 、 碘甲烷 在 2,2,6,6-四甲基哌啶 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以75%的产率得到tricarbonyl-[η6-1,3-dimethoxy-5-methyl-2-trimethylsilylbenzene]chromium(0)
  参考文献：
  名称：

  摘要：

  Two variants of synthesis of resveratrol (3,5,4'-trans-trihydroxystilbene) from dimethyl ether and anisaidehyde were performed using the chromium eta(6)-benzenetricarbonyl complex. The Wittig-Horner reactions or aldol condensation in four stages followed by demethylation by EtSLi were applied.

  DOI：

  10.1023/a:1020921101384

文献信息

• ——
  作者：K. E. Polunin、H.-G. Schmalz、I. A. Polunina

  DOI：10.1023/a:1020921101384

  日期：——

  Two variants of synthesis of resveratrol (3,5,4'-trans-trihydroxystilbene) from dimethyl ether and anisaidehyde were performed using the chromium eta(6)-benzenetricarbonyl complex. The Wittig-Horner reactions or aldol condensation in four stages followed by demethylation by EtSLi were applied.
• Application of Chromium-Arene Complexes in the Organic Synthesis. Efficient Synthesis of Stilbene Phytoalexins
  作者：K. E. Polunin、H.-G. Schmalz

  DOI：10.1023/b:ruco.0000022800.70211.7d

  日期：2004.4

  Planar chiral eta(6)-arene-Cr(CO)(3) complexes represent highly valuable building blocks for the diastereo- and enantioselective synthesis. Their employment as synthons offer new and unique opportunities for the stereoselective multistep synthesis of complex natural products. The strategy of novel efficient synthesis of stilbene phytoalexins was based on arene chromium chemistry and the chemical and stereochemical effects of the metal unit on the reactivity of complexed arene ligand and stereochemical features of such compounds. Two variants for the construction of the trans-stilbene and diarylethanol framework via facilitated benzylic deprotonation of an eta(6)-benzene-Cr(CO)(3) complex and subsequent coupling with para-anisaidehyde in an aldol-type or a Wittig-Horner reaction were suggested.