cis-2,5-Dibromocyclopentanone | 52906-75-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-2,5-Dibromocyclopentanone
• 英文别名: 2,5-dibromocyclopentan-1-one；trans-2,5-dibromocyclopentanone；trans-2,5-dibromocyclopentenone；(+/-)-trans-2,5-dibromo-cyclopentanone；(+/-)-trans-2,5-Dibrom-cyclopentanon
• CAS: 52906-75-9；53778-21-5；61209-44-7
• 化学式: C₅H₆Br₂O
• 分子量: 241.91
• InChiKey: NCQGXAFVNKDKRW-QWWZWVQMSA-N

物化性质

• 沸点：
  243.6±40.0 °C(Predicted)
• 密度：
  2.123±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  8.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

安全信息

• 海关编码：
  2914700090

反应信息

• 作为反应物：
  描述：

  cis-2,5-Dibromocyclopentanone 在 palladium on activated charcoal diiron nonacarbonyl 、 氢气 作用下， 以 苯 为溶剂， 生成 抗-三环[4.2.1.12,5]癸烷-9-酮
  参考文献：
  名称：

  Regioselectivity in cycloadditions of singlet 2-methylenecyclopenta-1,3-diyl species

  摘要：

  DOI：

  10.1021/ja00531a032
• 作为产物：
  描述：

  环戊酮 在 1,4-二氧六环 、 乙醚 、 溴 作用下， 生成 cis-2,5-Dibromocyclopentanone
  参考文献：
  名称：

  Matschinskaja; Podberesina, Zhurnal Obshchei Khimii, 1958, vol. 28, p. 1501; engl. Ausg. S. 1550

  摘要：

  DOI：

文献信息

• Formation of α-iminoketones and α-diimines versus Favorskii rearrangement products from the reaction of α,α′-dibromoketones and primary amines
  作者：Norbert De Kimpe、Luc D'Hondt、Luc Mones

  DOI：10.1016/s0040-4020(01)92258-6

  日期：1992.4

  reaction of aliphatic acyclic α,α′-dibromoketones with primary amines gave rise to α-iminoketones and α-diimines. Both reaction products could be selectively obtained under appropriate reaction conditions. Sterically hindered α,α-dibromoketones did not react with primary amines, although, under forcing conditions the Favorskii rearrangement could be induced. In aqueous methanol, α,α′-dibromoketones reacted

  脂族无环α，α′-二溴酮与伯胺的反应产生α-亚氨基酮和α-二亚胺。两种反应产物都可以在适当的反应条件下选择性地获得。受位阻的α，α-二溴酮不与伯胺反应，尽管在强迫条件下可以诱导Favorskii重排。在甲醇水溶液中，α，α'-二溴代酮与伯胺反应生成Favorskii重排，而不是α-亚氨基酮的形成。脂环族α，α'-二溴代酮对伯胺的行为不同，因为五元环提供2-（N-烷基）氨基-2-环戊烯酮，而六元环引起Favosskii环收缩。
• Attempted Generation of an Observable Ethano-Bridged (Cyclopentyl) Oxyallyl. The Pericyclic Nature of an Oxyallyl-Oxyallyl Dimerization Reaction
  作者：A. P. Masters、M. Parvez、T. S. Sorensen、F. Sun

  DOI：10.1021/ja00086a013

  日期：1994.4

  An attempt is made to directly observe an ethano-bridged (cyclopentyl) oxyallyl using a synthetic methodolgy which employs aprotic solvents and homogeneous conditions involving a novel organometallic reagent and which can be carried out at very low temperatures. However, even with preparation temperatures of -120 degrees C, the 2,5-dimethylcyclopentyl oxyallyl is not observable by in situ NMR spectroscopy. Products corresponding to an oxyallyl + oxyallyl dimerization are observed instead. The major dimer is a cis-dioxane compound, and the formation of this suggests a process under pericyclic control. An analysis of the allowed molecular orbital overlaps is presented, and it is concluded that the mutual overlap involves all three terminal orbitals (overlap 2 in Figure 2), with preferential bond formation taking place between carbon(A)-oxygen(B), oxygen(A)-carbon(B), where A and B are the two oxyallyl monomers. The dioxane product represents only one of four possible double-connectivity ways in which two oxyallyl units can be joined (see Figure 1). The initially formed cis-dioxane product is quite labile and is easily transformed in a sequential and stereospecific manner into products representative of two of the other three connectivity modes. The formation of the parent cyclopentyl oxyallyl was also studied under the same reaction conditions. In this case one sees no dimeric products, but the formation of the oxyallyl is indicated because [4 + 3] diene adducts of the putative oxyallyl can be trapped, in; accord with previous work in this area.
• .alpha.,.alpha.'-Dibromocycloalkanones. Preparation and conformation
  作者：H. M. R. Hoffman、J. G. Vinter

  DOI：10.1021/jo00940a027

  日期：1974.12