(2S,3S,4R,5S)-2-hydroxy-4-methoxy-3,5-dimethylcyclohexanone | 216174-73-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4R,5S)-2-hydroxy-4-methoxy-3,5-dimethylcyclohexanone
• 英文别名: (2S,3S,4R,5S)-2-hydroxy-4-methoxy-3,5-dimethylcyclohexan-1-one
• CAS: 216174-73-1
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: LWZGESJPSZQLPB-UXXCCHNYSA-N

物化性质

• 沸点：
  267.0±40.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.61
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 (2S,3S,4R,5S)-2-hydroxy-4-methoxy-3,5-dimethylcyclohexanone 在 lead(IV) acetate 作用下， 以 甲醇 、 苯 为溶剂， 以78%的产率得到methyl (3S,4R,5R)-6-oxo-4-methoxy-3,5-dimethylhexanoate
  参考文献：
  名称：

  Total synthesis of (−)-pironetin

  摘要：

  The convergent total synthesis of (-)-pironetin using a chiral building block, (1S,5S,6R)-5-hydroxybicyclo[4.1.0]heptan-2-one 5 is described Both the dithiane 4 and the epoxide 2 with proper substituents were employed as coupling partners to construct the whole carbon skeleton 15, which was converted to pironetin 1 in a few steps. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01860-7
• 作为产物：
  描述：

  (1R,4S,5S,6S)-5-methoxy-4-methylbicyclo<4.1.0>heptan-2-one 在 lead(IV) acetate 、 氨 、 lithium 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， 反应 40.17h， 生成 (2S,3S,4R,5S)-2-hydroxy-4-methoxy-3,5-dimethylcyclohexanone
  参考文献：
  名称：

  An efficient synthesis of pironetins employing a useful chiral building block,(1S,5S,6R)-5-hydroxybicyclo[4.1.0]heptan-2-one

  摘要：

  A convergent total synthesis of pironetin 1 and related compound 2 using a chiral building block, (1S,5S,6R)-5-hydroxybicyclo[4.1.0]heptan-2-one 5 is described. Both the dithiane 47 and the epoxide 32 with proper substituents were employed as coupling partners to construct the whole carbon skeleton 48, which was converted to (-)-pironetin 1 and (-)-2 in few steps. The usefulness of 5 for polyketide synthesis was demonstrated. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00556-6