1-(4-hydroxybutyl)cyclooctanol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-hydroxybutyl)cyclooctanol
• 英文别名: 1-(4-Hydroxybutyl)cyclooctan-1-ol
• 化学式: C₁₂H₂₄O₂
• 分子量: 200.321
• InChiKey: XWWWQWCBNHOJCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• 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

• 作为产物：
  描述：

  环辛酮 、 4-氯丁基苯基醚 在 di(tert-butyl)-biphenyl 、 lithium 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 2.08h， 以20%的产率得到1-(4-hydroxybutyl)cyclooctanol
  参考文献：
  名称：

  3-Chloropropyl and 4-Chlorobutyl Phenyl Ethers as Sources of 1,3-Dilithiopropane and 1,4-Dilithiobutane:  Sequential Reaction with Carbonyl Compounds

  摘要：

  The reaction of 3-chloropropyl and 4-chlorobutyl phenyl ethers (1) with lithium powder and a catalytic amount of DTBB (5% molar) in THF at -78 degrees C followed by successive treatment with a carbonyl compound [(RRCO)-R-1-C-2 = (BuCHO)-C-t, Me2CO, (CH2)(5)CO, (-)-menthone] at -78 to 20 degrees C and, after 1.5 h at this temperature, with a second one [(RRCO)-R-3-C-4 = (BuCHO)-C-t, PhCHO, Me2CO, MeCOPrn, (CH2)(5)CO, (-)-menthone] at -78 degrees C leads,after hydrolysis with water, to the corresponding 1,5- and 1,6-diols (2). Because of the competition of two different reductive cleavages, 1,4- and 1,5-diols 3 were also obtained as side-reaction products.

  DOI：

  10.1021/jo000039m

文献信息

• 3-Chloropropyl and 4-Chlorobutyl Phenyl Ethers as Sources of 1,3-Dilithiopropane and 1,4-Dilithiobutane:  Sequential Reaction with Carbonyl Compounds
  作者：Francisco Foubelo、Sadiq A. Saleh、Miguel Yus

  DOI：10.1021/jo000039m

  日期：2000.6.1

  The reaction of 3-chloropropyl and 4-chlorobutyl phenyl ethers (1) with lithium powder and a catalytic amount of DTBB (5% molar) in THF at -78 degrees C followed by successive treatment with a carbonyl compound [(RRCO)-R-1-C-2 = (BuCHO)-C-t, Me2CO, (CH2)(5)CO, (-)-menthone] at -78 to 20 degrees C and, after 1.5 h at this temperature, with a second one [(RRCO)-R-3-C-4 = (BuCHO)-C-t, PhCHO, Me2CO, MeCOPrn, (CH2)(5)CO, (-)-menthone] at -78 degrees C leads,after hydrolysis with water, to the corresponding 1,5- and 1,6-diols (2). Because of the competition of two different reductive cleavages, 1,4- and 1,5-diols 3 were also obtained as side-reaction products.