2-(2,3-dimethoxy-4-methyl-phenyl)-ethanol | 843610-73-1

• 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: 2-(2,3-dimethoxy-4-methyl-phenyl)-ethanol
• 英文别名: 2-(2,3-Dimethoxy-4-methylphenyl)ethanol
• CAS: 843610-73-1
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: RIKYMRRJTDWXBC-UHFFFAOYSA-N

物化性质

• 沸点：
  291.3±35.0 °C(Predicted)
• 密度：
  1.066±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2,3-dimethoxy-4-methyl-phenyl)-ethanol 在 溴 、 三苯基膦 作用下， 以87%的产率得到1-(2-Bromoethyl)-2,3-dimethoxy-4-methylbenzene
  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：

  环氧乙烷 、 2,3-二甲氧基甲苯 在 正丁基锂 作用下， 以60%的产率得到2-(2,3-dimethoxy-4-methyl-phenyl)-ethanol
  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.