(R)-3-(3-tert-butoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)-5,5-dimethylcyclohex-2-enone | 1202794-02-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-3-(3-tert-butoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)-5,5-dimethylcyclohex-2-enone
• CAS: 1202794-02-2
• 化学式: C₂₁H₃₇BO₄
• 分子量: 364.333
• InChiKey: PLHVIDUFCHAZNN-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.97
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R)-3-(3-tert-butoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)-5,5-dimethylcyclohex-2-enone 在 sodium peroxoborate tetrahydrate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以95%的产率得到(R)-3-(3-tert-butoxy-2-hydroxypropyl)-5,5-dimethylcyclohex-2-enone
  参考文献：
  名称：

  Vicinal Diboronates in High Enantiomeric Purity through Tandem Site-Selective NHC−Cu-Catalyzed Boron−Copper Additions to Terminal Alkynes

  摘要：

  A Cu-catalyzed protocol for conversion of terminal alkynes to enantiomerically enriched diboronates is reported. In a single vessel, a site-selective hydroboration of an alkyne leads to the corresponding terminal vinylboronate, which undergoes a second site-selective and enantioselective hydroboration. Reactions proceed in the presence of 2 equiv of commercially available bis(pinacolato)diboron [B-2(pin)(2)] and 5-7.5 mol % loading of a chiral bidentate imidazolinium salt, affording diboronates in 60-93% yield and up to 97.5:2.5 enantiomeric ratio (er). The enantiomerically enriched products can be functionalized to afford an assortment of versatile organic molecules. Enynes are converted to unsaturated diboronates with high chemo- (>98% reaction of alkyne; <2% at alkene) and enantioselectivity (e.g., 94.5:5.5 er).

  DOI：

  10.1021/ja9089928
• 作为产物：
  描述：

  5,5-二甲基-3-溴环己-2-烯酮 、 (R)-2-(3-tert-butoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 caesium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 14.0h， 以76%的产率得到(R)-3-(3-tert-butoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)-5,5-dimethylcyclohex-2-enone
  参考文献：
  名称：

  Vicinal Diboronates in High Enantiomeric Purity through Tandem Site-Selective NHC−Cu-Catalyzed Boron−Copper Additions to Terminal Alkynes

  摘要：

  A Cu-catalyzed protocol for conversion of terminal alkynes to enantiomerically enriched diboronates is reported. In a single vessel, a site-selective hydroboration of an alkyne leads to the corresponding terminal vinylboronate, which undergoes a second site-selective and enantioselective hydroboration. Reactions proceed in the presence of 2 equiv of commercially available bis(pinacolato)diboron [B-2(pin)(2)] and 5-7.5 mol % loading of a chiral bidentate imidazolinium salt, affording diboronates in 60-93% yield and up to 97.5:2.5 enantiomeric ratio (er). The enantiomerically enriched products can be functionalized to afford an assortment of versatile organic molecules. Enynes are converted to unsaturated diboronates with high chemo- (>98% reaction of alkyne; <2% at alkene) and enantioselectivity (e.g., 94.5:5.5 er).

  DOI：

  10.1021/ja9089928