4-bromo-5-methyl tropone

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 环庚三烯酮
• 英文名称: 4-bromo-5-methyl tropone
• 英文别名: 4-bromo-5-methyltropone；4-Bromo-5-methylcyclohepta-2,4,6-trien-1-one
• 化学式: C₈H₇BrO
• 分子量: 199.047
• InChiKey: PYYZKXHZCGKPME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-methyl-4-tribromomethylcyclohexa-2,5-dien-1-one 在 三苄胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以65%的产率得到4-bromo-5-methyl tropone
  参考文献：
  名称：

  4-三溴甲基-4-甲基-2,5-环己二酮与胺的新型光反应

  摘要：

  在胺的存在下辐照4-三溴甲基-4-甲基-2,5-环己二酮，得到了4-溴-5-甲基对苯二酚作为主要产物。基于获得的结果，提出了涉及从胺基态到二烯酮激发态的单电子转移的机理。

  DOI：

  10.1016/s0040-4039(00)78459-0

文献信息

• Photoreactions of 4-(Tribromomethyl)-4-methyl-2,5-cyclohexadienone and Its Derivatives with Amines:  Radical Cyclization and Ring Expansion Reactions Promoted through Photoinduced Electron Transfer Processes
  作者：Eietsu Hasegawa、Yukinobu Tamura、Kimiko Suzuki、Akira Yoneoka、Toshio Suzuki

  DOI：10.1021/jo990215v

  日期：1999.11.1

  Photoreactions of 4-(tribromomethyl)-4-methyl-2,5-cyclohexadienone (1) and its derivatives with amines were studied. Irradiation of 1 with amine produced 4-bromo-5-methyltropone (2) along with 4-(dibromomethyl)-4-methyl-2,5-cyclohexadienone (3). The effects of solvent, added water, and the structural variation in amine on the product ratio were explored. Isolation of the amine-derived products revealed

  研究了4-（三溴甲基）-4-甲基-2,5-环己二酮（1）及其衍生物与胺的光反应。用胺辐照1产生4-溴-5-甲基对苯二酮（2）以及4-（二溴甲基）-4-甲基-2,5-环己二酮（3）。探索了溶剂，加水和胺的结构变化对产物比率的影响。胺衍生产物的分离表明，胺的氧化脱烷基在光反应过程中进行。基于获得的结果，提出了涉及二烯酮阴离子-自由基和胺阳离子-自由基对的断裂的反应机理。二烯酮4与胺的光反应产生了6酮和7酮，而9酮则由8酮生成。三烷基锡自由基诱导的三正丁基氢化锡还原二烯酮1和4表现出光反应的共同特征。还发现用胺辐射二烯酮3可产生4-甲基对苯二酚（10）。
• Reductive transformation of α,β-epoxy ketones and other compounds promoted through photoinduced electron transfer processes with 1,3-dimethyl-2-phenylbenzimidazoline (DMPBI)
  作者：Eietsu Hasegawa、Akira Yoneoka、Kumiko Suzuki、Teru Kato、Takashi Kitazume、Kazuhiro Yanagi

  DOI：10.1016/s0040-4020(99)00804-2

  日期：1999.11

  Photoreactions of epoxy ketones, aromatic ketones, haloketones, and aromatic halides with 1,3-dimethyl-2-phenylbenzimidazoline (DMPBI) were studied Photoinduced single-electron transfer from DMPBI to such substrates initiates the reactions followed by radical radical rearrangement and reduction to finally give several reduced products in modest to good yields. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Reaction of 4-methyl-4-tribromomethylcyclohexa-2,5-dien-1-one with zinc metal
  作者：G. V. Gavrilova、A. A. Gavrilov、K. P. Butin

  DOI：10.1007/bf02495530

  日期：1998.1

  4-Methyl-4-tribromomethylcyclohexa-2,5-diene-1-one reacts with zinc dust in absolute DMF to give a mixture of 4-bromo-5-methylcyclohepta-2,4,6-trien-1-one, 4-methylcyclohepta-2,4,6-trien-1-one, and 4-dibromomethyl-4-methylcyclohexa-2,5-dien-1-one.
• Novel photoreaction of 4-tribromomethyl-4-methyl-2,5-cyclohexadienone with amine
  作者：Eietsu Hasegawa、Yukinobu Tamura、Takaaki Horaguchi、Koji Isogai、Toshio Suzuki

  DOI：10.1016/s0040-4039(00)78459-0

  日期：1994.11

  Irradiation of 4-tribromomethyl-4-methyl-2,5-cyclohexadienone in the presence of amines gave 4-bromo-5-methyltropone as a major product. On the basis of the results obtained, the mechanism involving single electron transfer from the amine ground state to the dienone excited state was proposed.

  在胺的存在下辐照4-三溴甲基-4-甲基-2,5-环己二酮，得到了4-溴-5-甲基对苯二酚作为主要产物。基于获得的结果，提出了涉及从胺基态到二烯酮激发态的单电子转移的机理。