(1R,4S,5S,6S)-5-methoxy-4-methylbicyclo<4.1.0>heptan-2-one | 216174-55-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,4S,5S,6S)-5-methoxy-4-methylbicyclo<4.1.0>heptan-2-one
• 英文别名: (1R,4S,5S,6S)-5-methoxy-4-methylbicyclo[4.1.0]heptan-2-one
• CAS: 216174-55-9
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: WAIBCTXGLHRRKQ-XQXXSGGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,4S,5S,6S)-5-methoxy-4-methylbicyclo<4.1.0>heptan-2-one 在 氨 、 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以75%的产率得到(3S,5S)-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
• 作为产物：
  描述：

  (1R,2S,4S,5S,6S)-5-methoxy-4-methylbicyclo<4.1.0>heptan-2-ol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以85%的产率得到(1R,4S,5S,6S)-5-methoxy-4-methylbicyclo<4.1.0>heptan-2-one
  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

文献信息

• Total synthesis of (−)-pironetin
  作者：Hiroyuki Watanabe、Hidenori Watanabe、Takeshi Kitahara

  DOI：10.1016/s0040-4039(98)01860-7

  日期：1998.11

  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.