(1R,2S,4S,5S,6S)-5-methoxy-4-methylbicyclo<4.1.0>heptan-2-ol | 216174-54-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S,4S,5S,6S)-5-methoxy-4-methylbicyclo<4.1.0>heptan-2-ol
• 英文别名: (1R,2S,4S,5S,6S)-5-methoxy-4-methylbicyclo[4.1.0]heptan-2-ol
• CAS: 216174-54-8
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: LLCOQVNIKXVWNM-BGKGJTHRSA-N

物化性质

• 沸点：
  249.7±8.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2S,4S,5S,6S)-5-methoxy-4-methylbicyclo<4.1.0>heptan-2-ol 在 lead(IV) acetate 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 41.5h， 生成 Acetic acid (1R,3S,4R,5R,6S)-5-methoxy-4-methyl-2-oxo-bicyclo[4.1.0]hept-3-yl ester
  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：

  (1S,5S,6R)-5-tetrahydropyranyloxybicyclo<4.1.0>heptan-2-one 在 盐酸 、 六甲基磷酰三胺 、 sodium hydroxide 、 正丁基锂 、 双氧水 、 四丁基碘化铵 、 L-Selectride 、 sodium hydride 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 11.5h， 生成 (1R,2S,4S,5S,6S)-5-methoxy-4-methylbicyclo<4.1.0>heptan-2-ol
  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.