(1-bromo-1-hexenyl)bis(1,2-dimethylpropyl)borane | 187874-60-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1-bromo-1-hexenyl)bis(1,2-dimethylpropyl)borane
• 英文别名: 1-bromo-1-hexenylbis(1,2-dimethylpropyl)borane；(Z)-1-bromo-1-hexenyldisiamylborane；[(Z)-1-bromohex-1-enyl]-bis(3-methylbutan-2-yl)borane
• CAS: 187874-60-8
• 化学式: C₁₆H₃₂BBr
• 分子量: 315.145
• InChiKey: BRVFFRUDAFHVJZ-WJDWOHSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.58
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  (1-bromo-1-hexenyl)bis(1,2-dimethylpropyl)borane 在 N,N-二甲基甲酰胺 、 N-溴代乙酰胺 作用下， 以 四氢呋喃 为溶剂， 生成 (E)-4-bromo-2,3-dimethyl-4-nonene
  参考文献：
  名称：

  Reaction of [(Z)-1-bromo-1-alkenyl]dialkylboranes with N-halogeno compound in THF–DMF: a novel synthesis of 1,2-disubstituted (E)-vinyl bromides

  摘要：

  DMF-induced reaction of [(Z)-1-bromo-1-alkenyl]dialkylboranes with an N-halogeno compound results in 1,2-migration of an alkyl group from the dialkylboryl group to the alpha-carbon atom without elimination of the bromine atom, followed by beta-elimination to provide 1,2-disubstituted (E)-vinyl bromides stereoselectively in good yields. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00213-6
• 作为产物：
  描述：

  1-bromohexyne 、 alkaline earth salt of/the/ methylsulfuric acid 生成 (1-bromo-1-hexenyl)bis(1,2-dimethylpropyl)borane
  参考文献：
  名称：

  （Z）-1-卤-1-烯基二烷基硼烷与氢化三丁基锡的立体选择性脱卤：氢化三丁基锡作为氢化物供体的行为

  摘要：

  （Z）-1-卤代-1-烯基二烷基硼烷（1）与氢化三丁基锡（n- Bu 3 SnH）在0°C或室温下的反应导致卤素原子的还原去除，得到（E）-或（Z）-1-烯基二烷基硼烷，其立体化学取决于二烷基硼基和1的烯基。

  DOI：

  10.1016/s0040-4039(96)02324-6

文献信息

• The Synthesis of Internal Conjugated (<i>E</i>)-Enynyldialkylboranes and Their Applications to the Syntheses of Conjugated Alkynones, Conjugated (<i>E</i>)-Enynes, and Conjugated Enynes Bearing an Unsaturated Group on the Double Bond
  作者：Masayuki Hoshi、Yuzuru Masuda、Akira Arase

  DOI：10.1246/bcsj.58.1683

  日期：1985.6

  (E)-Enynyldialkylboranes, thus obtained, gave regio- and/or stereospecifically defined corresponding conjugated alkynones by alkaline hydrogen peroxide oxidation, conjugated (E)-enynes by protonolysis with acetic acid, and conjugated enynes bearing an unsaturated group on the internal alkenyl carbon atom by bis(acetylacetonato)copper-catalyzed cross-coupling reaction with allyl bromide or 1-bromo-1-hexyne respectively

  内共轭 (E)-烯基二烷基硼烷是通过 1-iodo-1-炔烃与二烷基硼烷和 1-炔基锂的连续反应合成的，产率为 31-79%。由此获得的 (E)-烯基二烷基硼烷通过碱性过氧化氢氧化产生区域和/或立体特异性定义的相应共轭炔酮，通过用乙酸质子分解产生共轭 (E)-烯炔，以及在内部烯基碳上带有不饱和基团的共轭烯炔原子通过双（乙酰丙酮）铜催化的交叉偶联反应分别与烯丙基溴或 1-溴-1-己炔。
• A Novel Synthesis of Internal Alkenyldialkylborane by the Reaction of 1-Halo-1-alkenyldialkylborane with Grignard Reagent
  作者：Akira Arase、Masayuki Hoshi、Yuzuru Masuda

  DOI：10.1246/bcsj.57.209

  日期：1984.1

  To synthesize internal alkenyldialkylboranes, coupling reactions were carried out by using 1-halo-l-alkenyldialkylboranes and Grignard reagents. Hydrogen peroxide oxidation and protonolysis with acetic acid of the reaction product revealed that internal (E)-alkenyldialkylborane was formed in 60–90% yield.

  为了合成内部烯基二烷基硼烷，通过使用 1-卤代-l-烯基二烷基硼烷和格氏试剂进行偶联反应。过氧化氢氧化和反应产物的乙酸质子分解表明，内部 (E)-烯基二烷基硼烷以 60-90% 的产率形成。
• The Reactions of (1-Halo-1-alkenyl)dialkylboranes with Lead(IV) Acetate or (Diacetoxyiodo)benzene. A Stereoselective Synthesis of 1-Halo-1,2-dialkylethylenes
  作者：Yuzuru Masuda、Akira Arase、Akira Suzuki

  DOI：10.1246/bcsj.53.1652

  日期：1980.6

  The reaction of (1-halo-1-alkenyl)dialkylboranes with lead(IV) acetate or (diacetoxyiodo)benzene was studied. (1-Bromo-1-alkenyl)dialkylboranes gave 1-bromo-1,2-dialkylethylenes. When alkyl groups ...

  研究了（1-卤代-1-烯基）二烷基硼烷与乙酸铅（IV）或（二乙酰氧基碘）苯的反应。(1-溴-1-烯基)二烷基硼烷得到1-溴-1,2-二烷基亚乙基。当烷基...
• MASUDA YUZURU; ARASE AKIRA; SUZUKI AKIRA, CHEM. LETT., 1978, NO 7, 665-668
  作者：MASUDA YUZURU、 ARASE AKIRA、 SUZUKI AKIRA

  DOI：——

  日期：——
• Stereoselective dehalogenation of (Z)-1-halo-1-alkenyldialkylborane with tributyltin hydride: The behavior of tributyltin hydride as a hydride donor
  作者：Masayuki Hoshi、Kimitomo Takahata、Akira Arase

  DOI：10.1016/s0040-4039(96)02324-6

  日期：1997.1

  The reaction of (Z)-1-halo-1-alkenyldialkylborane (1) with tributyltin hydride (n-Bu3SnH) at 0 °C or room temperature results in reductive removal of the halogen atom to afford (E)- or (Z)-1-alkenyldialkylborane whose stereochemistry depends on the dialkylboryl group and the alkenyl group of 1.

  （Z）-1-卤代-1-烯基二烷基硼烷（1）与氢化三丁基锡（n- Bu 3 SnH）在0°C或室温下的反应导致卤素原子的还原去除，得到（E）-或（Z）-1-烯基二烷基硼烷，其立体化学取决于二烷基硼基和1的烯基。