2-(5-Methoxy-2-bromobenzyl)-3-methylcyclohex-2-en-1-one | 155855-21-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(5-Methoxy-2-bromobenzyl)-3-methylcyclohex-2-en-1-one
• 英文别名: 2-(2-bromo-5-methoxybenzyl)-3-methylcyclohex-2-en-1-one；2-[(2-Bromo-5-methoxyphenyl)methyl]-3-methylcyclohex-2-en-1-one
• CAS: 155855-21-3
• 化学式: C₁₅H₁₇BrO₂
• 分子量: 309.203
• InChiKey: FUAXGVSBJDLGAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(5-Methoxy-2-bromobenzyl)-3-methylcyclohex-2-en-1-one 在 氢氧化钾 、 sodium tert-pentoxide 作用下， 以 乙醚 、 乙醇 、 水 、 甲苯 为溶剂， 反应 115.0h， 生成 Methyl 2-(5-methoxy-2-bromobenzyl)-3-methyl-1-methylenecyclohexane-3-carboxylate
  参考文献：
  名称：

  Regioselective Aryl Radical Cyclization. 1. Stereocontrolled Synthesis of Linearly Condensed Hydroaromatic Carbocyclic Systems through 6-endo-Ring Closures

  摘要：

  The stereocontrolled synthesis of trans-octahydroanthracenes 3, 11a-c, and 14a-c and trans-octahydro-5aH-cyclohepta[b] naphthalene (27) through implementation of an efficient and highly regioselective 6-endo-trig-aryl radical cyclization of the respective 2-(o-bromoaryl)-1-methylenecyclohexanes 2, 10a-c, and 13a-c and 2-(o-bromobenzyl)-1-methylenecycloheptane (41) with tri-n- butyltin-hydride-is described. The radical cyclization of 2-(o-bromobenzyl)-1-methylenecyclopentane (43), in contrast, produced a mixture of the cis- and trans-hexahydro-1H-benz[f]indenes (38) and (37).

  DOI：

  10.1021/jo00089a009
• 作为产物：
  描述：

  2-溴-5-甲氧基溴苄 在 氢氧化钾 、 potassium tert-butylate 作用下， 以 乙醇 、 叔丁醇 为溶剂， 反应 30.0h， 生成 2-(5-Methoxy-2-bromobenzyl)-3-methylcyclohex-2-en-1-one
  参考文献：
  名称：

  Regioselective Aryl Radical Cyclization. 1. Stereocontrolled Synthesis of Linearly Condensed Hydroaromatic Carbocyclic Systems through 6-endo-Ring Closures

  摘要：

  The stereocontrolled synthesis of trans-octahydroanthracenes 3, 11a-c, and 14a-c and trans-octahydro-5aH-cyclohepta[b] naphthalene (27) through implementation of an efficient and highly regioselective 6-endo-trig-aryl radical cyclization of the respective 2-(o-bromoaryl)-1-methylenecyclohexanes 2, 10a-c, and 13a-c and 2-(o-bromobenzyl)-1-methylenecycloheptane (41) with tri-n- butyltin-hydride-is described. The radical cyclization of 2-(o-bromobenzyl)-1-methylenecyclopentane (43), in contrast, produced a mixture of the cis- and trans-hexahydro-1H-benz[f]indenes (38) and (37).

  DOI：

  10.1021/jo00089a009

文献信息

• Palladium‐Catalyzed Tandem γ‐Arylation/Aromatization of Cyclohex‐2‐En‐1‐One Derivatives: A Route to 3,4‐Dihydroanthracen‐1(2 <i>H</i> )‐Ones
  作者：Yi‐Kang Song、Si‐Yu Xu、Shu‐Sheng Zhang、Jian‐Guo Fu、Guo‐Qiang Lin、Chen‐Guo Feng

  DOI：10.1002/adsc.202001587

  日期：2021.6.21

  An intramolecular palladium-catalyzed tandem γ-arylation/aromatization reaction of cyclohex-2-en-1-one derivatives was developed. This work provides a simple and efficient approach for the construction of substituted 3,4-dihydroanthracen-1(2H)-ones in good yields with a broad substrate scope.

  开发了分子内钯催化的 cyclohex-2-en-1-one 衍生物的串联 γ-芳基化/芳构化反应。这项工作为构建具有广泛底物范围的高产率取代的 3,4-二氢蒽-1(2 H )-酮提供了一种简单有效的方法。
• Mukhopadhyaya, Jayanta K.; Pal, Sitaram; Ghatak, Usha Ranjan, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 3, p. 264 - 268
  作者：Mukhopadhyaya, Jayanta K.、Pal, Sitaram、Ghatak, Usha Ranjan

  DOI：——

  日期：——
• Pal Sitaram, Mukhopadhyaya Jayanta K., Ghatak Usha Ranjan, J. Org. Chem, 59 (1994) N 10, S 2687-2694
  作者：Pal Sitaram, Mukhopadhyaya Jayanta K., Ghatak Usha Ranjan

  DOI：——

  日期：——
• Regioselective Aryl Radical Cyclization. 1. Stereocontrolled Synthesis of Linearly Condensed Hydroaromatic Carbocyclic Systems through 6-endo-Ring Closures
  作者：Sitaram Pal、Jayanta K. Mukhopadhyaya、Usha Ranjan Ghatak

  DOI：10.1021/jo00089a009

  日期：1994.5

  The stereocontrolled synthesis of trans-octahydroanthracenes 3, 11a-c, and 14a-c and trans-octahydro-5aH-cyclohepta[b] naphthalene (27) through implementation of an efficient and highly regioselective 6-endo-trig-aryl radical cyclization of the respective 2-(o-bromoaryl)-1-methylenecyclohexanes 2, 10a-c, and 13a-c and 2-(o-bromobenzyl)-1-methylenecycloheptane (41) with tri-n- butyltin-hydride-is described. The radical cyclization of 2-(o-bromobenzyl)-1-methylenecyclopentane (43), in contrast, produced a mixture of the cis- and trans-hexahydro-1H-benz[f]indenes (38) and (37).