(2Z,4Z)-3-methylhexa-2,4-diene-1,6-dibromide | 260431-84-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: (2Z,4Z)-3-methylhexa-2,4-diene-1,6-dibromide
• 英文别名: (2Z,4Z)-1,6-Dibromo-3-methylhexa-2,4-diene
• CAS: 260431-84-3
• 化学式: C₇H₁₀Br₂
• 分子量: 253.964
• InChiKey: CKNQVGSNGUVJOR-JXPISWCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  9.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  丙二酸二甲酯 、 (2Z,4Z)-3-methylhexa-2,4-diene-1,6-dibromide 在 sodium methylate 作用下， 以 四氢呋喃 为溶剂， 反应 36.5h， 生成 4-methyl-1,1-dicarbomethoxy-cyclohepta-3,5-diene
  参考文献：
  名称：

  Easy Access to Medium Rings by Entropy/Strain Reduction. V. A Simple and Mild Route to Cyclohepta‐1,3‐dienes

  摘要：

  The Perkin ring closure reaction of various substituted open chain cis,cis hexa-2,4-diene-1,6-dibromides with either bis(phenylsulfonyl)methane or dimethyl malonate under basic conditions gives reasonable yields of cycloheptadienes (1-7). The presence of unsaturation in the starting material ameliorates the entropy and strain problems normally encountered in such medium rings closures.

  DOI：

  10.1081/scc-120030751
• 作为产物：
  描述：

  dimethyl (2Z,4Z)-3-methylhexa-2,4-diene-1,6-dioate 在 三溴化磷 、 二异丁基氢化铝 作用下， 以 乙醚 、 正己烷 、 甲苯 为溶剂， 反应 12.0h， 生成 (2Z,4Z)-3-methylhexa-2,4-diene-1,6-dibromide
  参考文献：
  名称：

  Easy access to medium rings by entropy/strain reduction. Part 2. The ready availability of cis,cis-2,4-diene-1,6-diols and derived dibromides allows a simple and mild route to substituted 2,7-dihydro-1H-azepines

  摘要：

  一系列取代的顺,顺-2,4-二烯-1,6-二羧酸酯1通过氢化物还原得到相应的1,6-二醇2,其中大部分在磷三溴存在下转化为1,6-二溴化物3。在碳酸氢钠存在下,这些二溴化物与伯烷基胺反应,提供了简单温和的取代二氢氮杂卓4的合成途径。使用对甲苯磺酰胺作为氮源时,产物最为纯净。双(二氢氮杂卓)5也从二胺合成,而肼生成肼盐6。在丁基锂存在下,苯胺可以参与反应,以低产率得到N-苯基二氢氮杂卓8。

  DOI：

  10.1039/a905387e

文献信息

• Easy access to medium rings by entropy/strain reduction. Part 2. The ready availability of cis,cis-2,4-diene-1,6-diols and derived dibromides allows a simple and mild route to substituted 2,7-dihydro-1H-azepines
  作者：James G. Walsh、Patrick J. Furlong、Declan G. Gilheany

  DOI：10.1039/a905387e

  日期：——

  Hydride reduction of a series of substituted cis,cis-2,4-diene-1,6-dioates 1 provided the corresponding 1,6-diols 2, most of which were converted to the 1,6-dibromides 3 with phosphorus tribromide. Reaction of a selection of these dibromides with primary alkylamines in the presence of sodium hydrogen carbonate provided a simple and mild synthesis of substituted dihydroazepines 4. The cleanest products were obtained with toluene-p-sulfonamide as the nitrogen source. Bis(dihydroazepines) 5 were also synthesised from diamines while hydrazine yielded a hydrazinium salt 6. Aniline could be induced to take part in the reaction in the presence of butyllithium furnishing a low yield of N-phenyldihydroazepines 8.

  一系列取代的顺,顺-2,4-二烯-1,6-二羧酸酯1通过氢化物还原得到相应的1,6-二醇2,其中大部分在磷三溴存在下转化为1,6-二溴化物3。在碳酸氢钠存在下,这些二溴化物与伯烷基胺反应,提供了简单温和的取代二氢氮杂卓4的合成途径。使用对甲苯磺酰胺作为氮源时,产物最为纯净。双(二氢氮杂卓)5也从二胺合成,而肼生成肼盐6。在丁基锂存在下,苯胺可以参与反应,以低产率得到N-苯基二氢氮杂卓8。
• Easy Access to Medium Rings by Entropy/Strain Reduction. V. A Simple and Mild Route to Cyclohepta‐1,3‐dienes
  作者：Louise A. Byrne、Patrick J. Furlong、Declan G. Gilheany

  DOI：10.1081/scc-120030751

  日期：2004.12.31

  The Perkin ring closure reaction of various substituted open chain cis,cis hexa-2,4-diene-1,6-dibromides with either bis(phenylsulfonyl)methane or dimethyl malonate under basic conditions gives reasonable yields of cycloheptadienes (1-7). The presence of unsaturation in the starting material ameliorates the entropy and strain problems normally encountered in such medium rings closures.