1-[(1S,2R)-2-(2-Hydroxy-ethyl)-1-methyl-cyclohexyl]-propan-1-one | 134389-46-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[(1S,2R)-2-(2-Hydroxy-ethyl)-1-methyl-cyclohexyl]-propan-1-one
• CAS: 134389-46-1
• 化学式: C₁₂H₂₂O₂
• 分子量: 198.305
• InChiKey: SYNDCIZPLOTPNV-PWSUYJOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.54
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 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-[(1S,2R)-2-(2-Hydroxy-ethyl)-1-methyl-cyclohexyl]-propan-1-one 在 aluminum oxide 、 重铬酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以89%的产率得到((1R,2S)-2-Methyl-2-propionyl-cyclohexyl)-acetaldehyde
  参考文献：
  名称：

  Asymmetric syntheses of 1,6-dialkyl-1,4-cyclohexadiene derivatives

  摘要：

  Ortho-lithiation-alkylation of tertiary benzamide 3 provides a series of 2-substituted chiral benzamides 3a-g (Scheme 1). Birch reduction of 3a-j followed by alkylation of the resulting chiral amide enolate with MeI at -78-degress-C gives 1,6-di-alkyl-1,4-cyclohexadiene derivatives 4a-j with excellent diastereoselectivities (Table I). Applications of this asymmetric synthesis are illustrated by conversions of 4g to enantiomerically pure bicyclic lactone 9 and octalone 11 (Scheme III) and 4j to hexahydro-9-anthracenone 14 (Scheme IV).

  DOI：

  10.1021/ja00013a032
• 作为产物：
  描述：

  (1S,2S,2'S)-2-<2<(trimethylsilyl)ethoxy>ethyl>-1-methyl-1-<<2'-(methoxymethyl)pyrrolidinyl>carbonyl>cyclohexane 在 三氟化硼乙醚 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 46.5h， 生成 1-[(1S,2R)-2-(2-Hydroxy-ethyl)-1-methyl-cyclohexyl]-propan-1-one
  参考文献：
  名称：

  Asymmetric syntheses of 1,6-dialkyl-1,4-cyclohexadiene derivatives

  摘要：

  Ortho-lithiation-alkylation of tertiary benzamide 3 provides a series of 2-substituted chiral benzamides 3a-g (Scheme 1). Birch reduction of 3a-j followed by alkylation of the resulting chiral amide enolate with MeI at -78-degress-C gives 1,6-di-alkyl-1,4-cyclohexadiene derivatives 4a-j with excellent diastereoselectivities (Table I). Applications of this asymmetric synthesis are illustrated by conversions of 4g to enantiomerically pure bicyclic lactone 9 and octalone 11 (Scheme III) and 4j to hexahydro-9-anthracenone 14 (Scheme IV).

  DOI：

  10.1021/ja00013a032