2-(2-cyclohexylprop-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | 1187524-92-0

• 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: 2-(2-cyclohexylprop-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 英文别名: (Z)-2-(2-cyclohexyl-1-propenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane；2-[(Z)-2-cyclohexylprop-1-enyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 1187524-92-0
• 化学式: C₁₅H₂₇BO₂
• 分子量: 250.189
• InChiKey: MGPTYGBGTJHTFD-QXMHVHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-cyclohexylprop-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 在 水 、 sodium hydroxide 、 碘 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.17h， 以88%的产率得到(Z)-(1-iodoprop-1-en-2-yl)cyclohexane
  参考文献：
  名称：

  Highly Regio- and Stereoselective Synthesis of (Z)-Trisubstituted Alkenes via Propyne Bromoboration and Tandem Pd-Catalyzed Cross-Coupling

  摘要：

  Contrary to all previous reports, bromoboration of propyne with BBr3 proceeds in >= 98% syn-selectivity to produce (Z)-2-bromo-1-propenyldibromoborane (1). Although 1 is readily prone to stereoisomerization, it can be converted to the pinacolboronate (2) of >= 98% isomeric purity by treatment with pinacol, which may then be subjected to Negishi coupling to give trisubstituted (Z)-alkenylpinacolboronates (3) containing various R groups in 73-90% yields. Iodinolysis of 3 affords alkenyl iodides (4) in 80-90% yields. All alkenes isolated and identified are >= 98% Z

  DOI：

  10.1021/ol901566e
• 作为产物：
  描述：

  (Z)-2-(2-bromoprop-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 、 环己基溴化镁 在 zinc dibromide 、 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.5h， 以84%的产率得到2-(2-cyclohexylprop-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  Highly Regio- and Stereoselective Synthesis of (Z)-Trisubstituted Alkenes via Propyne Bromoboration and Tandem Pd-Catalyzed Cross-Coupling

  摘要：

  Contrary to all previous reports, bromoboration of propyne with BBr3 proceeds in >= 98% syn-selectivity to produce (Z)-2-bromo-1-propenyldibromoborane (1). Although 1 is readily prone to stereoisomerization, it can be converted to the pinacolboronate (2) of >= 98% isomeric purity by treatment with pinacol, which may then be subjected to Negishi coupling to give trisubstituted (Z)-alkenylpinacolboronates (3) containing various R groups in 73-90% yields. Iodinolysis of 3 affords alkenyl iodides (4) in 80-90% yields. All alkenes isolated and identified are >= 98% Z

  DOI：

  10.1021/ol901566e

文献信息

• Stereoselective Synthesis of Trisubstituted Alkenylboron Reagents by Boron-Wittig Reaction of Ketones
  作者：Sheila Namirembe、Chenpeng Gao、Ryan P. Wexler、James P. Morken

  DOI：10.1021/acs.orglett.9b01663

  日期：2019.6.7

  Application of the boron-Wittig reaction to ketone electrophiles provides a straightforward route to trisubstituted alkenylboronic esters. With either a pentamethyldiethylenetriamine or trimethyl-1,4,7-triazacyclononane additive, the olefination can occur with very high levels of stereocontrol and in good chemical yield.

  硼-维蒂希反应在酮亲电子试剂上的应用为三取代的烯基硼酸酯提供了一条直接途径。与五甲基二亚乙基三胺或三甲基-1,4,7-三氮杂环壬烷添加剂一起使用时，可以以很高的立体控制水平和良好的化学收率进行烯化反应。