(2S)-5-chloropentane-1,2-diol | 1315024-01-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S)-5-chloropentane-1,2-diol
• CAS: 1315024-01-1
• 化学式: C₅H₁₁ClO₂
• 分子量: 138.594
• InChiKey: CXKSDHSPMIXCBS-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-5-chloropentane-1,2-diol 、 苯甲酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 、
  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：

  (R)-2,2'-(5-chloropentane-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)-5-chloropentane-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