2-(5-Methoxy-2-bromobenzyl)-3,3-dimethyl-1-methylenecyclohexane | 155855-28-0

• 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)-3,3-dimethyl-1-methylenecyclohexane
• 英文别名: 1-Bromo-2-[(2,2-dimethyl-6-methylidenecyclohexyl)methyl]-4-methoxybenzene
• CAS: 155855-28-0
• 化学式: C₁₇H₂₃BrO
• 分子量: 323.273
• InChiKey: BKVTVAIVNQAJDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(5-Methoxy-2-bromobenzyl)-3,3-dimethyl-1-methylenecyclohexane 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 6.0h， 以65%的产率得到trans-1,1-Dimethyl-1,2,3,4,4a,9,9a,10-octahydro-7-methoxyanthracene
  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-(5-Methoxy-2-bromobenzyl)-3-methylcyclohex-2-en-1-one 在 LiCu 、 三氟化硼乙醚 、 sodium tert-pentoxide 作用下， 以 甲苯 为溶剂， 反应 6.33h， 生成 2-(5-Methoxy-2-bromobenzyl)-3,3-dimethyl-1-methylenecyclohexane
  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

• An Efficient Palladium Catalyzed Stereocontrolled Synthesis of 4a-Angular Methyl Substituted Hydrofluorenes
  作者：Jayanta K. Mukhopadhyaya、Sitaram Pal、Usha Ranjan Ghatak

  DOI：10.1080/00397919508015849

  日期：1995.6

  A high yield s tereoselective synthesis of 4a-angularly methyl substituted cis-hexahydrofluorenes 5a-h and tetrahydrofluorenes 7a,b has been developed by palladium-catalyzed intramolecular Heck-type cyclization of the respective exo-olefins 4a-h and 4a,b through exclusive 5-exo-trig mode.
• 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).