(E)-4-Bromo-4-octene | 24291-80-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-4-Bromo-4-octene
• 英文别名: (E)-4-bromooct-4-ene；E-4-bromo-4-octene
• CAS: 24291-80-3
• 化学式: C₈H₁₅Br
• 分子量: 191.111
• InChiKey: DZFWCWSQNWCLIS-BQYQJAHWSA-N

物化性质

• 沸点：
  186.3±9.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  (E)-4-Bromo-4-octene 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 4.0h， 生成 4-octene
  参考文献：
  名称：

  Approximate absolute rate constants for the reactions of tributyltin radicals with aryl and vinyl halides

  摘要：

  DOI：

  10.1021/jo00025a040
• 作为产物：
  描述：

  meso-4,5-dibromooctane 在 potassium phosphate 、 1-butyl-3-methylimidazolium Tetrafluoroborate 作用下， 以 乙二醇二甲醚 为溶剂， 反应 3.0h， 生成 (E)-4-Bromo-4-octene
  参考文献：
  名称：

  由邻位二溴烷烃和芳基硼酸一锅法合成取代苯乙烯

  摘要：

  在包含 1,2-二甲氧基乙烷、N-丁基-N'-甲基咪唑鎓四氟硼酸盐（或溴化四丁基铵）和碱的体系中邻位二溴烷烃的脱溴化氢，以及随后钯催化的由此形成的溴代烯烃与芳基硼酸的交叉偶联取代苯乙烯。

  DOI：

  10.1007/s11172-007-0020-5

文献信息

• Palladium-catalyzed phosphorus–carbon bond formation: cross-coupling reactions of alkyl phosphinates with aryl, heteroaryl, alkenyl, benzylic, and allylic halides and triflates
  作者：Karla Bravo-Altamirano、Zhihong Huang、Jean-Luc Montchamp

  DOI：10.1016/j.tet.2005.03.107

  日期：2005.6

  palladium catalysis. This full paper examines the scope and some mechanistic aspects of this phosphorus–carbon bond forming reaction. The reactions of alkenyl and allylic halides are also described for the first time. This novel cross-coupling provides a convenient access to a variety of substituted H-phosphinates.

  H-芳基次膦酸酯和相关化合物的直接形成可以使用钯催化来完成。这篇全文探讨了这种磷-碳键形成反应的范围和一些机理方面。还首次描述了烯基和烯丙基卤化物的反应。这种新颖的交叉偶联可方便地获得各种取代的H-次膦酸酯。
• Stereochemistry of the wurtz-fittig preparation of vinylsilanes
  作者：Paul F. Hudrlik、Ashok K. Kulkarni、Sadhana Jain、Anne M. Hudrlik

  DOI：10.1016/s0040-4020(01)88586-0

  日期：1983.1

  The reactions of vinyl chlorides, bromides and iodides with sodium and trimethylsilyl chloride to give vinylsilanes have been shown to be stereospecific, with nearly complete retention of double bond configuration.

  氯乙烯，溴化物和碘化物与钠和三甲基甲硅烷基氯的反应生成乙烯基硅烷已显示具有立体特异性，几乎完全保留了双键构型。
• The use of chlorosubstituted cyclopropenium cations for the synthesis of substituted cyclopropenones.
  作者：Jonathan M White、Mark K Bromley

  DOI：10.1016/s0040-4039(00)60623-8

  日期：1993.6

  2-chlorocyclopropenyl cations (3) which are readily prepared from the corresponding 2-chlorocyclopropenes (4) by reaction with triphenylcarbenium tetrafluoroborate are converted to cyclopropenones (7) in high yield upon treatment with aqueous sodium bicarbonate.

  由相应的2-氯环丙烯（4）通过与四氟硼酸三苯基碳鎓反应容易制得的2-氯环丙烯基阳离子（3）在用碳酸氢钠水溶液处理后以高收率转化为环丙烯酮（7）。
• Bromide assisted addition of hydrogen bromide to alkynes and allenes
  作者：Hilton M. Weiss、Kim M. Touchette

  DOI：10.1039/a703569a

  日期：——

  The addition of 0.1 M quaternary ammonium bromide to a solution of 20% trifluoroacetic acid in methylene chloride causes a large rate increase in the reaction of non-conjugated alkynes. The initial vinyl bromide product reacts further to provide a mixture of isomeric vinyl bromides and dibromides. At high salt concentrations however, the secondary reactions are prevented and only the initial vinyl

  向20％三氟乙酸的二氯甲烷溶液中添加0.1 M溴化季铵盐会使非共轭炔烃的反应速率大大提高。起始的乙烯基溴化物产物进一步反应，以提供异构的乙烯基溴化物和二溴化物的混合物。然而，在高盐浓度下，可以防止副反应，并且仅发现起始的乙烯基溴。与烯烃的相应添加相反，提出的主要机理是通过卤离子对酸性炔烃π络合物进行一步一步，一致的亲核攻击，从而直接生成卤化乙烯。涉及syn的次要路径另外还可以看到。在所有盐浓度下，丙二烯都会产生大量的重排产物，表明阳离子机制的重要参与。
• Surface-Mediated Reactions. 4. Hydrohalogenation of Alkynes
  作者：Paul J. Kropp、Scott D. Crawford

  DOI：10.1021/jo00090a031

  日期：1994.6

  The use of appropriately prepared silica gel and alumina has been found to mediate the addition of hydrogen halides to alkynes. The technique has been rendered even more convenient by the use of various organic and inorganic acid halides that react in the presence of silica gel or alumina to generate hydrogen halides in situ. Treatment in this fashion of 1-propynylbenzene (1), which underwent no reaction in CH2Cl2 solution saturated with HCl, readily afforded the syn addition product, alkenyl chloride (E)-4a. On extended treatment (E)-4a underwent subsequent isomerization to the thermodynamically more stable Z isomer. Thus either isomer of 4a could be obtained in good yield depending on the reaction conditions. In a similar way bromides (E)- and (Z)-4b were obtained without competing formation of the radical products (E)- and (Z)-5, which occurred in solution. In contrast with solution-phase hydriodination of alkyne 1, which slowly afforded iodide (E)-4c, surface-mediated addition readily afforded (E)-4c, followed by isomerization to the Z isomer. E reversible arrow Z equilibration of the alkenyl halides 4 was shown to involve, at least in part, addition-elimination via the gem-dihalides 13. Analogous behavior was exhibited by the phenylalkynes 2 and 3 on surface-mediated hydrohalogenation. Surface-mediated addition of Hbr and HI to the internal alkylalkyne 14 afforded principally the anti addition products (Z)-15b,c. Treatment of the terminal alkynes 17 and 22 with (COBr)(2) over alumina gave the dibromides 20 and 24/25,respectively, whereas use of acetyl bromide as the Hbr precursor afforded the alkenyl bromides 18b and 23.