1-cyclohexyl-1-hydroxy-4,4-dimethylpentan-3-one | 65651-67-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-cyclohexyl-1-hydroxy-4,4-dimethylpentan-3-one
• CAS: 65651-67-4
• 化学式: C₁₃H₂₄O₂
• 分子量: 212.332
• InChiKey: PQHSMKNINNLOKU-UHFFFAOYSA-N

物化性质

• 沸点：
  318.2±15.0 °C(Predicted)
• 密度：
  0.968±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-cyclohexyl-1-hydroxy-4,4-dimethylpentan-3-one 在 双[Α,Α-双(三氟甲基)苯甲醇合]二苯硫 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以99%的产率得到5-cyclohexyl-2,2-dimethyl-4-penten-3-one
  参考文献：
  名称：

  SmI₂-Promoted Reformatsky-Type Coupling Reactions in Exceptionally Hindered Contexts

  摘要：

  Highly substituted, very hindered enones were synthesized using a two-step procedure that utilizes a diiodosamarium-promoted Reformatsky-type coupling and dehydration using Martin sulfurane. Both alpha-chloro- and alpha-bromoketones were coupled with a variety of carbonyl nucleophiles to form the intermediate beta-hydroxyketones, occurring with excellent diastereoselectivity, favoring the syn isomer (R-1 = Me). This technique complements other methods,and enables the preparation of enones outside of the scope of current olefination methodology.

  DOI：

  10.1021/ol800099a
• 作为产物：
  描述：

  1-溴频哪酮 、 环己烷基甲醛 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 1.42h， 以94%的产率得到1-cyclohexyl-1-hydroxy-4,4-dimethylpentan-3-one
  参考文献：
  名称：

  SmI₂-Promoted Reformatsky-Type Coupling Reactions in Exceptionally Hindered Contexts

  摘要：

  Highly substituted, very hindered enones were synthesized using a two-step procedure that utilizes a diiodosamarium-promoted Reformatsky-type coupling and dehydration using Martin sulfurane. Both alpha-chloro- and alpha-bromoketones were coupled with a variety of carbonyl nucleophiles to form the intermediate beta-hydroxyketones, occurring with excellent diastereoselectivity, favoring the syn isomer (R-1 = Me). This technique complements other methods,and enables the preparation of enones outside of the scope of current olefination methodology.

  DOI：

  10.1021/ol800099a

文献信息

• Eichenauer,H. et al., Angewandte Chemie, 1978, vol. 90, p. 219 - 220
  作者：Eichenauer,H. et al.

  DOI：——

  日期：——
• Chini, Marco; Crotti, Paolo; Gardelli, Cristina, Gazzetta Chimica Italiana, 1993, vol. 123, # 12, p. 673 - 676
  作者：Chini, Marco、Crotti, Paolo、Gardelli, Cristina、Minutolo, Filippo、Pineschi, Mauro

  DOI：——

  日期：——
• NARASAKA, KOICHI;MIWA, TETSUO;HAYASHI, HIROKI;OHTA, MASAKO, CHEM. LETT., 1984, N 8, 1399-1402
  作者：NARASAKA, KOICHI、MIWA, TETSUO、HAYASHI, HIROKI、OHTA, MASAKO

  DOI：——

  日期：——