(R)-2,2'-(hexane-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) | 1198172-04-1

• 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: (R)-2,2'-(hexane-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 英文别名: Me(CH2)3CH(B(pinacolato))CH2B(pinacolato)；Me(CH2)3CH(B(pin))CH2B(pin)
• CAS: 1198172-04-1
• 化学式: C₁₈H₃₆B₂O₄
• 分子量: 338.103
• InChiKey: NNKUMTVWFHYFGK-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.73
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R)-2,2'-(hexane-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 在 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.33h， 生成 (2S)-hexane-1,2-diol
  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：

  1-己炔 、 联硼酸频那醇酯 在 CuCl 、 NaOC(CH₃)3 、 (O₃SC₆H₄)(((CH₃)2CH)3C₆H₂)(C₆H₅)2C₃H₃N₂ 作用下， 以 tetrahydrofuran 为溶剂， 以84%的产率得到(R)-2,2'-(hexane-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
  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

文献信息

• Iridium-catalyzed enantioselective hydrogenation of vinyl boronates
  作者：Alexander Paptchikhine、Pradeep Cheruku、Mattias Engman、Pher G. Andersson

  DOI：10.1039/b912590f

  日期：——

  The first Ir-catalyzed asymmetric hydrogenations of vinyl boronates have been performed using low catalyst loadings (0.5 mol%) and pressure (as low as 1 bar). Good selectivities (76–98% ee) were obtained for a range of substrates.

  首次采用低催化剂负载量（0.5 mol%）和低压（低至1 bar）进行Ir催化的不对称氢化反应，取得了良好的选择性（76–98% ee），适用于多种底物。