(2-cyclohexenyl)dicyclohexylborane

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2-cyclohexenyl)dicyclohexylborane
• 英文别名: Cyclohex-2-en-1-yl(dicyclohexyl)borane
• 化学式: C₁₈H₃₁B
• 分子量: 258.255
• InChiKey: DUGILMZHUWHMLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.26
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  6-噁双环[3.1.0]-3-己烯 、 (2-cyclohexenyl)dicyclohexylborane 在 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.0h， 以64%的产率得到(2Z)-1-(2-cyclohexenyl)-2,4-pentadien-1-ol
  参考文献：
  名称：

  Syntheses with Organoboranes. XI. Allylboration of Vinylic Epoxides with Allylic Dialkylboranes

  摘要：

  Allylboration of representative vinylic epoxides with allyldiethylborane (1) and (2-cyclahexenyl)dicyclohexyl borane (2) affords the corresponding 1,2- and 1,4-addition products. cis-1,2-Addition is favored in the reaction of 1 with 3,4-epoxycycloalkenes of six- to eight-membered rings. 3,4-Epoxycyclopentene (3a) and 5,5-dimethyl-3,4-epoxycyclopentene (3b) undergo five-membered ring opening during allylboration with 1 and 2, producing the corresponding (Z)-trienols (4a and 4b) with high stereoselectivity. 1,4-Addition of 1 and 2 to monoepoxides of 1,3-butadiene and isoprene is favored, producing predominantly the corresponding (E)-alcohols.

  DOI：

  10.1021/ol006641g
• 作为产物：
  描述：

  bis(cyclohexanyl)borane 、 1,3-环己二烯 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (2-cyclohexenyl)dicyclohexylborane
  参考文献：
  名称：

  烯丙基硼烷的亲电子氰化：含有烯丙基季碳中心的β，γ-不饱和腈的合成†

  摘要：

  报道了烯丙基硼烷的亲电子氰化，该方法适用于烯丙基季碳中心的构建。该反应具有宽的底物范围和高的官能团耐受性。结果代表了制备合成有用的β，γ-不饱和腈（包括使用现有方法难以获得的衍生物）的前所未有的强大工具。该方法的合成效用通过产物氰基的官能团相互转化进一步证明。

  DOI：

  10.1039/c8cc09229j

文献信息

• Novel Amidoalkylation of 4-Acetoxyazetidinones with Allylic Boranes. A Stereoselective Entry into the Tribactams
  作者：Tino Rossi、Stefano Biondi、Stefania Contini、Russell J. Thomas、Carla Marchioro

  DOI：10.1021/ja00142a045

  日期：1995.9
• Electrophilic cyanation of allylic boranes: synthesis of β,γ-unsaturated nitriles containing allylic quaternary carbon centers
  作者：Kensuke Kiyokawa、Shotaro Hata、Shunpei Kainuma、Satoshi Minakata

  DOI：10.1039/c8cc09229j

  日期：——

  The electrophilic cyanation of allylic boranes, a process that is applicable to the construction of allylic quaternary carbon centers, is reported. The reaction has a broad substrate scope with a high functional group tolerance. The results represent an unprecedented and powerful tool for preparing synthetically useful β,γ-unsaturated nitriles, including derivatives that have been difficult to access

  报道了烯丙基硼烷的亲电子氰化，该方法适用于烯丙基季碳中心的构建。该反应具有宽的底物范围和高的官能团耐受性。结果代表了制备合成有用的β，γ-不饱和腈（包括使用现有方法难以获得的衍生物）的前所未有的强大工具。该方法的合成效用通过产物氰基的官能团相互转化进一步证明。
• Syntheses with Organoboranes. XI. Allylboration of Vinylic Epoxides with Allylic Dialkylboranes
  作者：Marek Zaidlewicz、Marek P. Krzemiński

  DOI：10.1021/ol006641g

  日期：2000.11.1

  Allylboration of representative vinylic epoxides with allyldiethylborane (1) and (2-cyclahexenyl)dicyclohexyl borane (2) affords the corresponding 1,2- and 1,4-addition products. cis-1,2-Addition is favored in the reaction of 1 with 3,4-epoxycycloalkenes of six- to eight-membered rings. 3,4-Epoxycyclopentene (3a) and 5,5-dimethyl-3,4-epoxycyclopentene (3b) undergo five-membered ring opening during allylboration with 1 and 2, producing the corresponding (Z)-trienols (4a and 4b) with high stereoselectivity. 1,4-Addition of 1 and 2 to monoepoxides of 1,3-butadiene and isoprene is favored, producing predominantly the corresponding (E)-alcohols.