1-¹³C-6-bromo-4,4-diphenylcyclohex-2-enone | 1026325-08-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-¹³C-6-bromo-4,4-diphenylcyclohex-2-enone
• 英文别名: 6-bromo-4,4-diphenyl(113C)cyclohex-2-en-1-one
• CAS: 1026325-08-5
• 化学式: C₁₈H₁₅BrO
• 分子量: 328.209
• InChiKey: LATXGKJZNFVVIA-CAAGJAQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-¹³C-6-bromo-4,4-diphenylcyclohex-2-enone 在 lithium carbonate 、 lithium bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 以76%的产率得到1-¹³C-4,4-diphenyl-2,5-cyclohexadienone
  参考文献：
  名称：

  4,4-Diphenylcyclohexa-2,5-dienylidene:  Rearrangement via an Isobenzene Pathway

  摘要：

  Pyrolytic decompostition of the Li salt of the tosylhydrazone of 4,4-diphenyl-2,5-cyclohexadienone produces a mixture of products which includes biphenyl, p-terphenyl, the azine of 4,4-diphenyl-2,5-cyclohexadienone, and o-terphenyl. C-13 labeling studies and computational results (semiempirical AM1 and density functional B3LYP/6-31G* molecular orbital calculations) elucidate the mechanistic pathway for the formation of o-terphenyl. A single mechanism is involved which proceeds through formation of an isobenzene species followed by subsequent phenyl and hydrogen migrations.

  DOI：

  10.1021/jo982400z
• 作为产物：
  描述：

  2-¹³C-5,5-diphenyl-2-acetoxy-1,3-cyclohexadiene 在 溴 作用下， 以 四氯化碳 为溶剂， 反应 3.0h， 以89%的产率得到1-¹³C-6-bromo-4,4-diphenylcyclohex-2-enone
  参考文献：
  名称：

  4,4-Diphenylcyclohexa-2,5-dienylidene:  Rearrangement via an Isobenzene Pathway

  摘要：

  Pyrolytic decompostition of the Li salt of the tosylhydrazone of 4,4-diphenyl-2,5-cyclohexadienone produces a mixture of products which includes biphenyl, p-terphenyl, the azine of 4,4-diphenyl-2,5-cyclohexadienone, and o-terphenyl. C-13 labeling studies and computational results (semiempirical AM1 and density functional B3LYP/6-31G* molecular orbital calculations) elucidate the mechanistic pathway for the formation of o-terphenyl. A single mechanism is involved which proceeds through formation of an isobenzene species followed by subsequent phenyl and hydrogen migrations.

  DOI：

  10.1021/jo982400z