1,5-dibromo-1,5-cyclooctadiene

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 1,5-dibromo-1,5-cyclooctadiene
• 英文别名: 1,5-Dibromocyclo-octa-1,5-diene；(1E,5E)-1,5-dibromocycloocta-1,5-diene
• 化学式: C₈H₁₀Br₂
• 分子量: 265.975
• InChiKey: ZOHNJFPKANRXOY-ABHPZVFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  phenylmagnesium bromide 、 1,5-dibromo-1,5-cyclooctadiene 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 作用下， 以 乙醚 为溶剂， 反应 12.0h， 以90%的产率得到1,5-diphenyl-1,5-cyclooctadiene
  参考文献：
  名称：

  Enantiomerically Pure Rhodium Complexes Bearing 1,5-Diphenyl-1,5-cyclooctadiene as a Chiral Diene Ligand. Their Use as Catalysts for Asymmetric 1,4-Addition of Phenylzinc Chloride

  摘要：

  A rhodium complex coordinated with 1,5-diphenyl-1,5-cyclooctadiene (Ph-cod), [RhCl((R)-Ph-cod)](2), was obtained enantiomerically pure through optical resolution of diastereomeric isomers [Rh(Ph-cod)((R)-1,1'-binaphthyl-2,2'-diamine)]BF4. The enantiomerically pure rhodium complexes showed high catalytic activity and enantioselectivity (up to 98% ee) in the asymmetric 1,4-addition of phenylzinc chloride to alpha,beta-unsaturated ketones and esters in the presence of chlorotrimethylsilane.

  DOI：

  10.1021/ol0524914
• 作为产物：
  描述：

  1-Brom-1,5-cyclooctadien 在 1,4-dioxane dibromide 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.0h， 生成 1,5-dibromo-1,5-cyclooctadiene
  参考文献：
  名称：

  Detert, Heiner; Rose, Bernd; Mayer, Winfried, Chemische Berichte, 1994, vol. 127, # 8, p. 1529 - 1532

  摘要：

  DOI：

文献信息

• 3 + 2 Cycloaddition via a Diels-Alder/retro-Diels-Alder sequence: Tandem cyclopentadienyl annulation of a 1,5-cyclooctadiyne synthetic equivalent
  作者：Alfonso Dávila、Merrikh S. Ramezanian、Frank R. Fronczek、Mark L. McLaughlin

  DOI：10.1016/0040-4039(96)00384-x

  日期：1996.4

  A novel method of synthesizing a 1,2-bis(ethano) bridged bis(cyclopentadienyl) compound, 6,13-diisopropylidenetricyclo[9.3.01,11.04,8]tetradeca-1(14),4,7,11-tetraene, 5, via a tandem Diels-Alder/retro-Diels-Alder sequence using a 1,5-cyclooctadiyne synthetic equivalent and 6,6-dimethylfulvene i is reported.

  一种合成1,2-双（乙醇）桥联双（环戊二烯基）化合物6,13-​​二异丙基亚氨基三环[9.3.0 1,11 .0 4,8 ] tetradeca-1（14），4,7，的新方法报道了通过串联的Diels-Alder / retro-Diels-Alder序列使用1，5-环辛二炔合成当量和6，6-二甲基富勒烯i的11-四烯，5。
• Design of a Ribosyltriazole-Annulated Cyclooctyne for Oligonucleotide Labeling by Strain-Promoted Alkyne-Azide Cycloaddition
  作者：Pieter van Delft、Wilbert de Witte、Nico J. Meeuwenoord、Gerbrand J. van der Heden van Noort、Frank Versluis、Rene C. L. Olsthoorn、Herman S. Overkleeft、Gijs A. van der Marel、Dmitri V. Filippov

  DOI：10.1002/ejoc.201403086

  日期：2014.12

  A ribosyltriazole ring-fused cyclooctyne was prepared and converted into the corresponding phosphoramidite, which was applied in the automated synthesis of DNA and RNA oligomers. Ensuing strain-promoted alkyne–azide cycloaddition of the obtained oligonucleotides to fluorescent azides yielded the corresponding fluorescent oligonucleotide conjugates.

  制备了核糖基三唑环稠合环辛炔并将其转化为相应的亚磷酰胺，用于 DNA 和 RNA 寡聚体的自动合成。随后将获得的寡核苷酸与荧光叠氮化物进行应变促进的炔-叠氮化物环加成反应，产生相应的荧光寡核苷酸缀合物。
• 1,5-Dibromocycloocta-1,5-diene
  作者：A. Dávila、M. L. McLaughlin、F. R. Fronczek、S. F. Watkins

  DOI：10.1107/s0108270196012322

  日期：1997.1.15

  The molecule of the title compound, C8H10Br2, lies on a crystallographic twofold axis, The eight-membered ring has a twist-boat conformation in which the two olefin planes form a dihedral angle of 74.7 (1)degrees with one another, The C-Br distance is 1.928(3) Angstrom and the C=C distance is 1.314(3) Angstrom.
• Detert, Heiner; Rose, Bernd; Mayer, Winfried, Chemische Berichte, 1994, vol. 127, # 8, p. 1529 - 1532
  作者：Detert, Heiner、Rose, Bernd、Mayer, Winfried、Meier, Herbert

  DOI：——

  日期：——
• Enantiomerically Pure Rhodium Complexes Bearing 1,5-Diphenyl-1,5-cyclooctadiene as a Chiral Diene Ligand. Their Use as Catalysts for Asymmetric 1,4-Addition of Phenylzinc Chloride
  作者：Asato Kina、Kazuhito Ueyama、Tamio Hayashi

  DOI：10.1021/ol0524914

  日期：2005.12.1

  A rhodium complex coordinated with 1,5-diphenyl-1,5-cyclooctadiene (Ph-cod), [RhCl((R)-Ph-cod)](2), was obtained enantiomerically pure through optical resolution of diastereomeric isomers [Rh(Ph-cod)((R)-1,1'-binaphthyl-2,2'-diamine)]BF4. The enantiomerically pure rhodium complexes showed high catalytic activity and enantioselectivity (up to 98% ee) in the asymmetric 1,4-addition of phenylzinc chloride to alpha,beta-unsaturated ketones and esters in the presence of chlorotrimethylsilane.

表征谱图