(-)-(R)-1-bromo-3-methyl-1,2-hexadiene | 41793-37-7

• 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: (-)-(R)-1-bromo-3-methyl-1,2-hexadiene
• 英文别名: 1-bromo-3-methyl-1,2-hexadiene
• CAS: 41793-37-7
• 化学式: C₇H₁₁Br
• 分子量: 175.068
• InChiKey: BNGDPJFEHUSUGH-UHFFFAOYSA-N

物化性质

• 沸点：
  175.0±7.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  (-)-(R)-1-bromo-3-methyl-1,2-hexadiene 以71%的产率得到
  参考文献：
  名称：

  CAPORUSSO, ANNA MARIA;CONSOLONI, CARLA;LARDICCI, LUCIANO, GAZZ. CHIM. ITAL., 118,(1988) N2, C. 857-859

  摘要：

  DOI：
• 作为产物：
  描述：

  Methanesulfonic acid (S)-1-ethynyl-1-methyl-butyl ester 在 Li⁽¹⁺⁾*Br₃Cu₂H^(1-) 作用下， 以 四氢呋喃 为溶剂， 生成 (-)-(R)-1-bromo-3-methyl-1,2-hexadiene
  参考文献：
  名称：

  Caporusso, Anna Maria; Consoloni, Carla; Lardicci, Luciano, Gazzetta Chimica Italiana, 1988, vol. 118, # 12, p. 857 - 860

  摘要：

  DOI：

文献信息

• Reactions of 3-alkyl- and 3,3-dialkyl-1-bromoallenes with organocuprates: Effects of the nature of the cuprate reagent on the regio- and stereoselectivity
  作者：Anna Maria Caporusso、Carmela Polizzi、Luciano Lardicci

  DOI：10.1016/s0040-4039(00)96867-9

  日期：1987.1

  Organocuprates induce 1,3- and direct substitution in 3-alkyl- and 3,3-dialkyl-1-bromo-1,2-dienes leading respectively to either terminal acetylenes or allenic hydrocarbons. The nature of the cuprate exerts a prominent role in determining both the regio- and the stereochemistry of these reactions.

  有机酸盐诱导3-烷基-和3,3-二烷基-1-溴-1,2-二烯中的1,3-和直接取代，分别导致末端乙炔或烯丙烃。铜酸盐的性质在确定这些反应的区域化学和立体化学中起着重要作用。
• Reaction of 1-bromo-1,2-dienes with alkylcuprates as a regio- and stereo-selective route to acetylenic or allenic compounds
  作者：Carmela Polizzi、Carla Consoloni、Luciano Lardicci、Anna Maria Caporusso

  DOI：10.1016/0022-328x(91)80179-n

  日期：1991.10

  Alkylcuprates react with 1-bromo-1,2-dienes to give allenic and/or acetylenic products. The selectivity of the crosscoupling is markedly dependent on the nature of the copper reagent, which plays a prominent role in determining both the regio- and the stereo-chemistry. The preparative aspects of these copper-induced reactions are discussed and their possible mechanism discussed.

  烷基杯酸酯与1-溴-1,2-二烯反应生成烯丙基和/或炔属产物。交叉偶联的选择性显着取决于铜试剂的性质，铜试剂在决定区域化学和立体化学方面都起着重要的作用。讨论了这些铜诱导的反应的制备方面，并讨论了其可能的机理。
• Coupling of chiral 1-bromo-1,2-dienes with zinc-based cuprates: a new procedure for the regio and stereoselective synthesis of functionalized acetylenic compounds
  作者：Anna Maria Caporusso、Sara Filippi、Federica Barontini、Piero Salvadori

  DOI：10.1016/s0040-4039(99)02249-2

  日期：2000.2

  are found to be active in the cross-coupling reaction with allenic bromides affording acetylenic products with a high regio and stereoselective 1,3-anti substitution. The coupling process, which has been successfully extended to functionalized cuprates, can also be performed with alkylzinc chlorides in the presence of catalytic amounts of cuprous salts.

  发现烷基氰基古朴酸锌（Knochel试剂）在与烯丙基溴的交叉偶联反应中具有活性，从而提供具有高区域和立体选择性1,3-抗取代作用的炔属产物。偶联过程已经成功地扩展到官能化的铜酸盐，也可以在催化量的亚铜盐存在下用烷基锌氯化物进行偶联。
• Direct Determination of the Enantiomeric Purity of Chiral Trisubstituted Allenes by Using Permethylated Cyclodextrin as a Chiral Solvating Agent
  作者：Gloria Uccello-Barretta、Federica Balzano、Anna Maria Caporusso、Piero Salvadori

  DOI：10.1021/jo00083a026

  日期：1994.2

  The heptakis(2,3,6-tri-O-methyl)-beta-cyclodextrin (TRIMEB) has been successfully used as convenient chiral solvating agent to determine the enantiomeric composition of chiral trisubstituted allenes by H-1 NMR spectroscopy: the analysis of the effect of the molar ratio TRIMEB/allene, temperature, and nature of the solvent allowed us to optimize the experimental conditions to enhance the separation between the signals of the two enantiomers of each allene.
• Landor,P.D. et al., Journal of the Chemical Society. Perkin transactions I, 1975, p. 1628 - 1632
  作者：Landor,P.D. et al.

  DOI：——

  日期：——