[1-(3,5-dimethoxy-phenyl)-cyclohexa-2,5-dienyl]-acetic acid methyl ester | 912580-95-1

• 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: [1-(3,5-dimethoxy-phenyl)-cyclohexa-2,5-dienyl]-acetic acid methyl ester
• 英文别名: Methyl 2-[1-(3,5-dimethoxyphenyl)cyclohexa-2,5-dien-1-yl]acetate；methyl 2-[1-(3,5-dimethoxyphenyl)cyclohexa-2,5-dien-1-yl]acetate
• CAS: 912580-95-1
• 化学式: C₁₇H₂₀O₄
• 分子量: 288.343
• InChiKey: SPNFSMICEQIAAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [1-(3,5-dimethoxy-phenyl)-cyclohexa-2,5-dienyl]-acetic acid methyl ester 在 sodium tetrahydroborate 、 正丁基锂 、 二异丁基氢化铝 、 sodium sulfate 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 10.0h， 生成 3a-(3,5-dimethoxy-phenyl)-1-(2-methoxy-1-phenyl-ethyl)-2,3,3a,6,7,7a-hexahydro-1H-indole
  参考文献：
  名称：

  Desymmetrization of Cyclohexa-2,5-dienes through a Diastereoselective Protonation−Hydroamination Cascade

  摘要：

  Intramolecular hydroamination of cyclohexa-2,5-dienes led with high selectivity to the corresponding bicyclic allylic amines. This study demonstrates that the reaction does not proceed through a direct hydroamination of one of the diastereotopic olefins but more likely involves a diastereoselective protonation of a pentadienyl anion, followed by addition of a lithium amide across the double bond of the resulting 1,3-diene, and is concluded by a highly regioselective protonation of the final allylic anion.

  DOI：

  10.1021/ol0618353
• 作为产物：
  描述：

  3-hydroxy-5-methoxybiphenyl 在 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 丙酮 为溶剂， 反应 17.42h， 生成 [1-(3,5-dimethoxy-phenyl)-cyclohexa-2,5-dienyl]-acetic acid methyl ester
  参考文献：
  名称：

  Desymmetrization of Cyclohexa-2,5-dienes through a Diastereoselective Protonation−Hydroamination Cascade

  摘要：

  Intramolecular hydroamination of cyclohexa-2,5-dienes led with high selectivity to the corresponding bicyclic allylic amines. This study demonstrates that the reaction does not proceed through a direct hydroamination of one of the diastereotopic olefins but more likely involves a diastereoselective protonation of a pentadienyl anion, followed by addition of a lithium amide across the double bond of the resulting 1,3-diene, and is concluded by a highly regioselective protonation of the final allylic anion.

  DOI：

  10.1021/ol0618353

文献信息

• Desymmetrization of Cyclohexa-2,5-dienes through a Diastereoselective Protonation−Hydroamination Cascade
  作者：Raphaël Lebeuf、Frédéric Robert、Kurt Schenk、Yannick Landais

  DOI：10.1021/ol0618353

  日期：2006.10.1

  Intramolecular hydroamination of cyclohexa-2,5-dienes led with high selectivity to the corresponding bicyclic allylic amines. This study demonstrates that the reaction does not proceed through a direct hydroamination of one of the diastereotopic olefins but more likely involves a diastereoselective protonation of a pentadienyl anion, followed by addition of a lithium amide across the double bond of the resulting 1,3-diene, and is concluded by a highly regioselective protonation of the final allylic anion.