2-Bromo-4,5-benzo-2,4-cycloheptadien-1-one | 150545-66-7

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 2-Bromo-4,5-benzo-2,4-cycloheptadien-1-one
• 英文别名: 6-Bromo-8,9-dihydrobenzo[7]annulen-7-one
• CAS: 150545-66-7
• 化学式: C₁₁H₉BrO
• 分子量: 237.096
• InChiKey: FYBAJHDAHCGELV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  2-Bromo-4,5-benzo-2,4-cycloheptadien-1-one 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 、 四甲基乙二胺 、 叔丁基锂 、 草酸 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醇 、 氯仿 、 苯 为溶剂， 反应 60.75h， 生成 (6-trimethylsilyl-8,9-dihydro-7H-benzo[7]annulen-7-yl) acetate
  参考文献：
  名称：

  Construction of the colchicine framework via two consecutive cyclopropane-mediated ring-expansion reactions

  摘要：

  托品酮 19 是一种体现生物碱秋水仙碱 1 框架的分子，它的七元 B 环和 C 环都是通过环丙烷对六元环前体进行扩增而形成的。

  DOI：

  10.1039/p19960002217
• 作为产物：
  描述：

  1,1-dibromo-1a,2,3,7b-tetrahydro-1H-cyclopropanaphthalene 在 水 、 silver nitrate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 25.0~124.0 ℃ 、861.26 kPa 条件下， 反应 12.0h， 生成 2-Bromo-4,5-benzo-2,4-cycloheptadien-1-one
  参考文献：
  名称：

  A seven-membered-ring allene dimer: synthesis of 1,2-benzo-1,3,4-cycloheptatriene and attempted synthesis of 1,2-benzo-1,4,5-cycloheptatriene

  摘要：

  7,7-Dibromo-3,4-benzobicyclo[4.1.0]heptane (6) and 7,7-dibromo-2,3-benzobicyclo[4.1.0]heptane (14) have been synthesized and their silver ion-catalyzed reactions studied. Hydroxy alcohol 7a was converted to the corresponding vinyl bromide 10. Reaction of 10 with base gave the hydrocarbon 12, instead of the expected allene 4. Hydroxy alcohol 15a was converted to the corresponding mesylate 20, but all attempts to reduce 20 to the expected vinyl bromide 23 failed. Instead, unexpected ether 21 was obtained. Therefore, 15a was treated with PBr3 to give 22, which upon treatment with LiAlH4 gave the vinyl bromide 23. Reaction of 23 'with potassium tert-butoxide produced strained bicyclic allene 5, which underwent a dimerization to give 24. Addition of tetracyanoethylene to dimer 24 resulted in the formation of 26, whose structure was investigated by X-ray crystallography.

  DOI：

  10.1021/jo00072a016

文献信息

• Construction of the colchicine framework via two consecutive cyclopropane-mediated ring-expansion reactions
  作者：Martin G. Banwell、Mariana Berak、David C. R. Hockless

  DOI：10.1039/p19960002217

  日期：——

  The seven-membered B- and C-rings of tropone 19, a molecule which embodies the framework of the alkaloid colchicine 1, have both been constructed via cyclopropanemediated expansion of a six-membered ring precursor.

  托品酮 19 是一种体现生物碱秋水仙碱 1 框架的分子，它的七元 B 环和 C 环都是通过环丙烷对六元环前体进行扩增而形成的。
• A seven-membered-ring allene dimer: synthesis of 1,2-benzo-1,3,4-cycloheptatriene and attempted synthesis of 1,2-benzo-1,4,5-cycloheptatriene
  作者：Y. Kemal Yildiz、Hasan Secen、Mariusz Krawiec、William H. Watson、Metin Balci

  DOI：10.1021/jo00072a016

  日期：1993.9

  7,7-Dibromo-3,4-benzobicyclo[4.1.0]heptane (6) and 7,7-dibromo-2,3-benzobicyclo[4.1.0]heptane (14) have been synthesized and their silver ion-catalyzed reactions studied. Hydroxy alcohol 7a was converted to the corresponding vinyl bromide 10. Reaction of 10 with base gave the hydrocarbon 12, instead of the expected allene 4. Hydroxy alcohol 15a was converted to the corresponding mesylate 20, but all attempts to reduce 20 to the expected vinyl bromide 23 failed. Instead, unexpected ether 21 was obtained. Therefore, 15a was treated with PBr3 to give 22, which upon treatment with LiAlH4 gave the vinyl bromide 23. Reaction of 23 'with potassium tert-butoxide produced strained bicyclic allene 5, which underwent a dimerization to give 24. Addition of tetracyanoethylene to dimer 24 resulted in the formation of 26, whose structure was investigated by X-ray crystallography.