6-methyl-6-(benzyloxy)-2-heptanol | 1391906-63-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6-methyl-6-(benzyloxy)-2-heptanol
• CAS: 1391906-63-0
• 化学式: C₁₅H₂₄O₂
• 分子量: 236.354
• InChiKey: FEVVTEANWBKHSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  17.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  (E)-6-methyl-6-(benzyloxy)-2-heptene 在 (1,3-dimethylimidazol-2-ylidene)borane 、 双三氟甲烷磺酰亚胺 、 双氧水 、 sodium hydroxide 作用下， 以 1,2-二氯乙烷 、 甲醇 、 水 为溶剂， 反应 19.0h， 以6%的产率得到6-methyl-6-(benzyloxy)-3-heptanol
  参考文献：
  名称：

  Borenium Ion Catalyzed Hydroboration of Alkenes with N-Heterocyclic Carbene-Boranes

  摘要：

  Treatment of alkenes such as 3-hexene, 3-octene, and 1-cyclohexyl-1-butene with the N-heterocyclic carbene (NHC)-derived borane 2 and catalytic HNTf2 (Tf = trifluoromethanesulfonyl (CF3SO2)) effects hydroboration at room temperature. With 3-hexene, surprisingly facile migration of the boron atom from C(3) of the hexyl group to C(2) was observed over a time scale of minutes to hours. Oxidative workup gave a mixture of alcohols containing 2-hexanol as the major product. A similar preference for the C(2) alcohol was observed after oxidative workup of the 3-octene and 1-cyclohexyl-1-butene hydroborations. NHC-borenium cations (or functional equivalents) are postulated as the species that accomplish the hydroborations, and the C(2) selective migrations are attributed to the four center interconversion of borenium cations with cationic NHC-borane-olefin pi-complexes.

  DOI：

  10.1021/ja305061c