5-Methyl-1-benzoyl-1,2,2a,3-tetrahydrobenzindole | 155997-37-8

• 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: 5-Methyl-1-benzoyl-1,2,2a,3-tetrahydrobenzindole
• 英文别名: (5-methyl-2a,3-dihydro-2H-benzo[cd]indol-1-yl)-phenylmethanone
• CAS: 155997-37-8
• 化学式: C₁₉H₁₇NO
• 分子量: 275.35
• InChiKey: AZZMOXRZEHWVAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-Methyl-1-benzoyl-1,2,2a,3-tetrahydrobenzindole 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 以84%的产率得到5-Methyl-4,5-exo-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：

  1-benzoyl-2,2a,3,4-tetrahydro-1H-benz[cd]indol-5-one 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 5.0h， 生成 5-Methyl-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

文献信息

• Heteroannulation process
  申请人：ELI LILLY AND COMPANY

  公开号：EP0564193A1

  公开（公告）日：1993-10-06

  A heteroannulation process for preparing piperidones and tetrahydropyridones by reacting an appropriately substituted enamine with an acryloyl derivative wherein a leaving group occupies the carbonyl; a process for cleaving a 1-phenylethyl group from an acylated amino group or an heterocyclic nitrogen atom adjacent to a carbonyl group, particularly that on the nitrogen atom of the products of the heteroannulation process, is also provided.

  通过将适当取代的恩胺与丙烯酰衍生物反应，从而制备哌啶酮和四氢吡啶酮的异构化过程，在其中一个离去基团占据羰基；还提供了一种从酰化氨基团或相邻于羰基的杂环氮原子上的1-苯乙基基团中裂解的过程，特别是在异构化过程产物的氮原子上的羰基。
• 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
  作者：Michael J. Martinelli、Barry C. Peterson、Vien V. Khau、Darrell R. Hutchison、M. Robert Leanna、James E. Audia、James J. Droste、Yun-Dong Wu、K. N. Houk

  DOI：10.1021/jo00087a042

  日期：1994.4

  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.