α-monobromobenz[f]indanone | 1027139-77-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: α-monobromobenz[f]indanone
• 英文别名: 2-bromobenz(4,5)indanone；2-Bromo-1,2-dihydrocyclopenta[b]naphthalen-3-one
• CAS: 1027139-77-0
• 化学式: C₁₃H₉BrO
• 分子量: 261.118
• InChiKey: BMWWVNOOHJHQPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  α-monobromobenz[f]indanone 在 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 2.0h， 生成 2-bromobenz(5,6)indene
  参考文献：
  名称：

  A Suzuki Coupling Based Route to 2,2‘-Bis(2-indenyl)biphenyl Derivatives

  摘要：

  Because of the promising performance in olefin polymerization of 2,2'-bis(2-indenyldiyl)biphenyl zirconium dichloride, we developed a new and broadly applicable route to 2,2'-bis(2-indenyl)biphenyl derivatives. Reaction of the known 2,2'-diiodobiphenyl (26) with the new 2-indenyl boronic acid (23) did not result in the desired 2,2'-bis(2-indenyl)biphenyl (10); instead an isomer thereof, (spiro-1,1-(2,2'-biphenyl)-2-(2-indenyl)indane) (27), was obtained. It was found that compound 10 could be made via a palladium-catalyzed reaction of 2,2-biphenyldiboronic acid (31) with 2-bromoindene (21) under standard Suzuki reaction conditions. However, the yield of this reaction was low at low palladium catalyst loadings, due to a competitive hydrolysis reaction of 2,2-biphenyldiboronic acid (31). HTE techniques were used to find an economically viable protocol. Thus, use of the commercially available 1.0 molar solution of (n-BU)(4)NOH in methanol with cosolvent toluene led to precipitation of the pure product in a fast and clean reaction, using only 0.7 mol % (0.35 mol % per C-C) of the expensive palladium catalyst.

  DOI：

  10.1021/jo016040i
• 作为产物：
  描述：

  四溴对烯 在 溴 、 sodium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.08h， 生成 α-monobromobenz[f]indanone
  参考文献：
  名称：

  Unlu, Cihansel Sancak; Tutar, Ahmet; Erenler, Ramazan, Journal of the Chemical Society of Pakistan, 2012, vol. 34, # 3, p. 705 - 708

  摘要：

  DOI：