(1E)-hex-1-en-1-yldichloroborane | 51207-21-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: (1E)-hex-1-en-1-yldichloroborane
• 英文别名: trans-1-hexen-1-yldichloroborane；dichloro(E-1-hexen-1-yl)borane；trans-1-Hexenyl-dichlorboran；trans-1-hexenyldichloroboran；trans-1-Hexenyldichlorboran；dichloro-[(E)-hex-1-enyl]borane
• CAS: 51207-21-7
• 化学式: C₆H₁₁BCl₂
• 分子量: 164.87
• InChiKey: JMPNCYDPZMBODL-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (1E)-hex-1-en-1-yldichloroborane 在 diazoacetic ester 作用下， 以 四氢呋喃 为溶剂， 生成 环己基乙酸乙酯
  参考文献：
  名称：

  Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: B: B-Verb.9, 5.2.5, page 200 - 205

  摘要：

  DOI：
• 作为产物：
  描述：

  1-己炔 在 dichloroborane ether 、 三氯化硼 作用下， 以 正戊烷 为溶剂， 生成 (1E)-hex-1-en-1-yldichloroborane
  参考文献：
  名称：

  Hydroboration. XLI. Hydroboration of alkenes and alkynes with dichloroborane etherates. Convenient procedures for the preparation of alkyl- and alkenyldichloroboranes and their derivatives

  摘要：

  DOI：

  10.1021/ja00423a026

文献信息

• Syntheses with organoboranes. IX. Vinyl- and 1-alkenyldichloroboranes as ethylene and 1-alkene equivalents for the Diels–Alder reaction
  作者：Marek Zaidlewicz、Jacek R Binkul、Wojciech Sokół

  DOI：10.1016/s0022-328x(98)01175-9

  日期：1999.5

  Vinyl- and 1-alkenyldichloroboranes were used as dienophiles for the Diels–Alder reaction with representative aliphatic and cyclic 1,3-dienes. The organoborane adducts were transformed into the corresponding olefins either by protonolysis or by oxidation–mesylation–reduction. Direct protonolysis of the adducts gave in most cases mixtures of olefins whereas the reduction of mesylates with lithium triethylborohydride

  乙烯基和1-烯基二氯硼烷被用作与亲脂性和环状1,3-二烯代表的狄尔斯-阿尔德反应的亲二烯体。有机硼烷加合物通过质子分解或氧化-甲磺酰化-还原转化为相应的烯烃。在大多数情况下，加合物的直接质子分解得到烯烃的混合物，而用三乙基硼氢化锂还原甲磺酸酯则可得到高纯度的纯烯烃。
• The reaction of alkynes with dichloroborane ethyl etherate in the presence of boron trichloride. A simple, general synthesis of alkenyldichloroboranes
  作者：Herbert C. Brown、N. Ravindran

  DOI：10.1016/s0022-328x(00)86509-2

  日期：1973.11

  The hydroboration of alkynes with dichloroborane ethyl etherate induced by boron trichloride in pentane gives alkenyldichloroboranes providing, for the first time, a simple, general synthesis of these compounds and their derivatives.

  由三氯化硼在戊烷中诱导的炔烃与二氯硼烷乙酸乙酯的硼氢化反应，得到烯基二氯硼烷，这首次提供了这些化合物及其衍生物的简单，通用的合成方法。
• Dienophilic activity of vinyldichloroboranes and their use as partners in Diels–Alder—reductive alkylation of azides in a one-pot reaction
  作者：Nicolas Noiret、Abdullah Youssofi、Bertrand Carboni、Michel Vaultier

  DOI：10.1039/c39920001105

  日期：——

  Vinyldichloroboranes react with 1,3-dienes and the sequence Diels–Alder cycloaddition–reductive alkylation of benzyl azide leads directly to secondary amines, therefore, showing that vinyldichloroboranes behave as synthetic equivalents of secondary enamines of defined stereochemistry.

  乙烯基二氯硼烷与1,3-二烯反应，序列Diels-Alder环加成-苄基叠氮化物的还原烷基化直接导致仲胺，因此，表明乙烯基二氯硼烷与定义立体化学的仲烯胺的合成等同物一样。
• Migration of 1-alkenyl groups from zirconium to boron compounds
  作者：Thomas E. Cole、Ramona Quintanilla、Stephan Rodewald

  DOI：10.1021/om00056a062

  日期：1991.10

  The reaction of dicyclopentadienylzirconium alkenyl chloride with a boron chloride or bromide results in the exchange of the halogen and alkenyl group, forming the alkenylborane. We report here a systematic investigation of the transmetalation of the 1-hexenyl group from zirconium to a variety of boron compounds. This group undergoes facile migration to a variety of boron compounds, yielding structurally different types of alkenylboranes in good to high yields. These results suggest that one can combine the unique reactivity and selectivity of hydrozirconation for the preparation of alkenylboranes.
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: B: B-Verb.9, 4.2.4.1, page 124 - 126
  作者：

  DOI：——

  日期：——