4,5-Dimethyl-1-benzoyl-1,2,2a,3-tetrahydrobenzindole | 155997-38-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4,5-Dimethyl-1-benzoyl-1,2,2a,3-tetrahydrobenzindole
• 英文别名: (4,5-dimethyl-2a,3-dihydro-2H-benzo[cd]indol-1-yl)-phenylmethanone
• CAS: 155997-38-9
• 化学式: C₂₀H₁₉NO
• 分子量: 289.377
• InChiKey: RQQNRFYWDPLSOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.63
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4,5-Dimethyl-1-benzoyl-1,2,2a,3-tetrahydrobenzindole 在 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 水 作用下， 生成 4,5-Dimethyl-4,5-exo-epoxy-1-benzoyl-1,2,2a,3,4,5-hexahydrobenzindole 、 4,5-Dimethyl-4,5-endo-epoxy-1-benzoyl-1,2,2a,3,4,5-hexahydrobenzindole
  参考文献：
  名称：

  Stereoselective Epoxidations and Electrophilic Additions to Partial Ergot Alkaloids and Conformationally-Fixed Styrenes. Experimental and Theoretical Modeling Evidence for the Importance of Torsional Steering as a Stereocontrol Element

  摘要：

  Partial ergot alkaloid substrates and related conformationally-fixed styrenes undergo epoxidation, osmium tetraoxide dihydroxylation, and hydrobromination with a level of stereoselectivity which cannot be explained by steric control but is consistent with electrophilic attack to minimize torsional strain. Force-field modeling is consistent with the importance of torsional steering as the dominant stereochemical control element.

  DOI：

  10.1021/jo00087a042
• 作为产物：
  描述：

  (5-Hydroxy-4,5-dimethyl-2a,3,4,5-tetrahydro-2H-benzo[cd]indol-1-yl)-phenyl-methanone 在 Amberlyst IR-15A resin 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 4,5-Dimethyl-1-benzoyl-1,2,2a,3-tetrahydrobenzindole
  参考文献：
  名称：

  Stereoselective Epoxidations and Electrophilic Additions to Partial Ergot Alkaloids and Conformationally-Fixed Styrenes. Experimental and Theoretical Modeling Evidence for the Importance of Torsional Steering as a Stereocontrol Element

  摘要：

  Partial ergot alkaloid substrates and related conformationally-fixed styrenes undergo epoxidation, osmium tetraoxide dihydroxylation, and hydrobromination with a level of stereoselectivity which cannot be explained by steric control but is consistent with electrophilic attack to minimize torsional strain. Force-field modeling is consistent with the importance of torsional steering as the dominant stereochemical control element.

  DOI：

  10.1021/jo00087a042