[3-[2-(2,3-Dimethoxy-4-methylphenyl)ethyl]-3-methylcyclopenten-1-yl]oxy-trimethylsilane | 843610-75-3

• 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: [3-[2-(2,3-Dimethoxy-4-methylphenyl)ethyl]-3-methylcyclopenten-1-yl]oxy-trimethylsilane
• CAS: 843610-75-3
• 化学式: C₂₀H₃₂O₃Si
• 分子量: 348.558
• InChiKey: FAHIJJYIVDMMFC-UHFFFAOYSA-N

物化性质

• 沸点：
  387.4±42.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.48
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [3-[2-(2,3-Dimethoxy-4-methylphenyl)ethyl]-3-methylcyclopenten-1-yl]oxy-trimethylsilane 在 lithium perchlorate 作用下， 以 异丙醇 、 乙腈 为溶剂， 生成 3-[2-(2,3-Dimethoxy-4-methyl-phenyl)-ethyl]-3-methyl-cyclopentanone 、 (3aS,9bR)-6,7-Dimethoxy-3a,8-dimethyl-2,3,3a,4,5,9b-hexahydro-cyclopenta[a]naphthalen-1-one
  参考文献：
  名称：

  Synthesis of the hamigeran skeleton through an electro-oxidative coupling reaction

  摘要：

  The tricyclic core of the hamigerans has been prepared through the use of a two-step electrochemical benzannulation reaction. The annulation proceeds through an initial conjugate addition of a phenethyl cuprate to 3-methlcyclopentenone with in situ silylation of the resulting enolate. Anodic oxidation effectively couples the pendant arene and the silyl enolether to produce a key intermediate for the synthesis of the natural products. Careful optimization revealed that the use of 'alcohol-free' conditions during the electrolysis was critical to obtain high yields of the annulated product. This method allowed the preparation. of the tricyclic core of hamigeran A and B in just four steps from commercially, available starting materials. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2004.11.108
• 作为产物：
  描述：

  2-(2,3-dimethoxy-4-methyl-phenyl)-ethanol 在 溴 、 magnesium 、 三苯基膦 作用下， 生成 [3-[2-(2,3-Dimethoxy-4-methylphenyl)ethyl]-3-methylcyclopenten-1-yl]oxy-trimethylsilane
  参考文献：
  名称：

  Synthesis of the hamigeran skeleton through an electro-oxidative coupling reaction

  摘要：

  The tricyclic core of the hamigerans has been prepared through the use of a two-step electrochemical benzannulation reaction. The annulation proceeds through an initial conjugate addition of a phenethyl cuprate to 3-methlcyclopentenone with in situ silylation of the resulting enolate. Anodic oxidation effectively couples the pendant arene and the silyl enolether to produce a key intermediate for the synthesis of the natural products. Careful optimization revealed that the use of 'alcohol-free' conditions during the electrolysis was critical to obtain high yields of the annulated product. This method allowed the preparation. of the tricyclic core of hamigeran A and B in just four steps from commercially, available starting materials. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2004.11.108

文献信息

• Synthesis of the hamigeran skeleton through an electro-oxidative coupling reaction
  作者：Jeffrey B. Sperry、Dennis L. Wright

  DOI：10.1016/j.tetlet.2004.11.108

  日期：2005.1

  The tricyclic core of the hamigerans has been prepared through the use of a two-step electrochemical benzannulation reaction. The annulation proceeds through an initial conjugate addition of a phenethyl cuprate to 3-methlcyclopentenone with in situ silylation of the resulting enolate. Anodic oxidation effectively couples the pendant arene and the silyl enolether to produce a key intermediate for the synthesis of the natural products. Careful optimization revealed that the use of 'alcohol-free' conditions during the electrolysis was critical to obtain high yields of the annulated product. This method allowed the preparation. of the tricyclic core of hamigeran A and B in just four steps from commercially, available starting materials. (C) 2004 Published by Elsevier Ltd.