2-(5-Methoxy-2-bromobenzyl)-3,3-dimethylcyclohexan-1-one | 150271-00-4

• 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-dimethylcyclohexan-1-one
• 英文别名: 2-[(2-Bromo-5-methoxyphenyl)methyl]-3,3-dimethylcyclohexan-1-one
• CAS: 150271-00-4
• 化学式: C₁₆H₂₁BrO₂
• 分子量: 325.246
• InChiKey: IINYOLYQZPGODS-UHFFFAOYSA-N

物化性质

• 沸点：
  400.2±25.0 °C(Predicted)
• 密度：
  1.251±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 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)-3,3-dimethylcyclohexan-1-one 在 偶氮二异丁腈 、 三正丁基氢锡 、 sodium tert-pentoxide 作用下， 以 甲苯 、 苯 为溶剂， 反应 11.0h， 生成 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：

  Ethyl 3-(5-methoxy-2-bromobenzyl)-2-methyl-4-oxocyclohex-2-enecarboxylate 在 氢氧化钾 、 LiCu 、 三氟化硼乙醚 作用下， 以 乙醇 为溶剂， 反应 15.33h， 生成 2-(5-Methoxy-2-bromobenzyl)-3,3-dimethylcyclohexan-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

• Highly regioselective 7-endo-aryl radical cyclisation: synthesis of octahydro-2H-dibenzo[a,d]cycloheptenes
  作者：Ajit K. Ghosh、Keya Ghosh、Sitaram Pal、Usha Ranjan Chatak

  DOI：10.1039/c39930000809

  日期：——

  A highly efficient 7-endo-trig-aryl radical cyclisation of the alkene 6 and the vinylcyclohexanols 11a–d with tri-n-butyltin hydride leading to the respective octahydro-2H-dibenzo[a,d]cycloheptene derivatives 7 and 8 and 12a–d is reported.

  报告了一种高效的7-内源三芳基自由基环化反应，使用三正丁基锡氢化物对烯烃6和乙烯基环己醇11a–d进行反应，生成相应的八氢-2H-二苯[a,d]环庚烯衍生物7、8和12a–d。
• Highly regioselective 8-endo-aryl radical cyclisation: a new synthetic route to decahydrodibenzo-[a,d]- and -[a,e]-cyclooctenols
  作者：Keya Ghosh、Ajit K. Ghosh、Usha Ranjan Ghatak

  DOI：10.1039/c39940000629

  日期：——

  A highly regioselective 8-endo-trig-aryl radical cyclisation of the vinylcyclohexanols 2a-c and allylcyclohexanols 6a-c with tri-n-butyltin hydride provides decahydrodibenzo-[a,e]- and -[a,d]-cyclooctenols 3a-c and 7a-c respectively, in moderate to good yields.

  用氢化三正丁基锡对乙烯基环己醇 2a-c 和烯丙基环己醇 6a-c 进行高区域选择性 8-内向-三芳基自由基环化反应，可分别得到十氢二苯并-[a,e]-和-[a,d]-环辛烯醇 3a-c 和 7a-c，收率中等至良好。
• Regioselective 9- aryl radical cyclisation: A new synthetic route to decahydro-5-dibenzo[a,d] and [a,e]-cyclononenols
  作者：Keya Ghosh、Usha Ranjan Ghatak

  DOI：10.1016/0040-4039(95)00880-l

  日期：1995.7
• 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：——