6-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)hex-5-en-1-yl methanesulfonate | 1144522-02-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 6-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)hex-5-en-1-yl methanesulfonate
• CAS: 1144522-02-0
• 化学式: C₁₂H₂₃BO₅S
• 分子量: 290.189
• InChiKey: MAOJXZBPLSWMTG-UHFFFAOYSA-N

物化性质

• 沸点：
  395.7±52.0 °C(predicted)
• 密度：
  1.10±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.79
• 重原子数：
  19.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  6-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)hex-5-en-1-yl methanesulfonate 、 正丁基氯化镁 在 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 以41%的产率得到1-cyclopentylpentan-1-ol
  参考文献：
  名称：

  Construction of Cyclopentyl Carbinols from ω-Tosyloxy-1-alkenyl Boronate Esters and Grignard Reagents

  摘要：

  Addition of RMgCl (R = n-Bu, Ph) to pinacol esters of 6-tosyloxy-1-alkenyl boronic acids at -78 degrees C gave the borates, which upon warming to room temperature underwent migration of R on boron to C(l) carbon and concomitant ring construction C-C bond formation between C(2) and C(6), eventually producing cyclopentyl alkyl (or aryl) carbinols after oxidative workup of the borane intermediates with 35% H2O2. Eight examples are presented and the reaction was applied to construction of a cyclohexyl carbinol.

  DOI：

  10.3987/com-08-s(f)69
• 作为产物：
  描述：

  、 2,2-二甲基-1,3-丙二醇 生成 6-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)hex-5-en-1-yl methanesulfonate
  参考文献：
  名称：

  Construction of Cyclopentyl Carbinols from ω-Tosyloxy-1-alkenyl Boronate Esters and Grignard Reagents

  摘要：

  Addition of RMgCl (R = n-Bu, Ph) to pinacol esters of 6-tosyloxy-1-alkenyl boronic acids at -78 degrees C gave the borates, which upon warming to room temperature underwent migration of R on boron to C(l) carbon and concomitant ring construction C-C bond formation between C(2) and C(6), eventually producing cyclopentyl alkyl (or aryl) carbinols after oxidative workup of the borane intermediates with 35% H2O2. Eight examples are presented and the reaction was applied to construction of a cyclohexyl carbinol.

  DOI：

  10.3987/com-08-s(f)69