(2S,5S)-2-pentyl-5-hydroxycarbonyl-1-cyclohexanone ethylene acetal | 146659-15-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,5S)-2-pentyl-5-hydroxycarbonyl-1-cyclohexanone ethylene acetal
• CAS: 146659-15-6
• 化学式: C₁₄H₂₄O₄
• 分子量: 256.342
• InChiKey: CYJBUHVAWGDQEL-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2S,5S)-2-pentyl-5-hydroxycarbonyl-1-cyclohexanone ethylene acetal 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以100%的产率得到(2S,5S)-2-pentyl-5-hydroxymethyl-1-cyclohexanone ethylene acetale
  参考文献：
  名称：

  Enantioselective synthesis of chiral liquid crystalline compounds from monoterpenes

  摘要：

  Chiral liquid crystalline compounds 1-9 have been synthesized enantioselectively from monoterpenes. The optical purities of (S)-(-)- and (R)-(+)-perillalcohol (16, 27). (S)-(-)- and (R)-(+)-1-pentyl-4-hydroxymethyl-1-cyclohexene (33, 34) and (2S,5S)-2-pentyl-5-hydroxymethyl-1-cyclohexanone (53) have been determined by H-1 NMR analysis using chiral shift reagents. The mesomorphic phases and transition temperatures of compounds 2,3,5,6,7,8 and 9 have been characterized.

  DOI：

  10.1016/s0040-4020(01)86265-7
• 作为产物：
  描述：

  (2S,5S)-(-)-2-pentyl-5-(2-propenyl)-1-cyclohexanone ethylene acetal 在 sodium hydroxide 、 二甲基硫 、 碘 、 臭氧 、 potassium iodide 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 生成 (2S,5S)-2-pentyl-5-hydroxycarbonyl-1-cyclohexanone ethylene acetal
  参考文献：
  名称：

  Enantioselective synthesis of chiral liquid crystalline compounds from monoterpenes

  摘要：

  Chiral liquid crystalline compounds 1-9 have been synthesized enantioselectively from monoterpenes. The optical purities of (S)-(-)- and (R)-(+)-perillalcohol (16, 27). (S)-(-)- and (R)-(+)-1-pentyl-4-hydroxymethyl-1-cyclohexene (33, 34) and (2S,5S)-2-pentyl-5-hydroxymethyl-1-cyclohexanone (53) have been determined by H-1 NMR analysis using chiral shift reagents. The mesomorphic phases and transition temperatures of compounds 2,3,5,6,7,8 and 9 have been characterized.

  DOI：

  10.1016/s0040-4020(01)86265-7