(1S,3R,6S)-3-hydroxy-3-(3-m-methoxyphenylpropyl)-6,8,8-trimethyl-2-oxabicyclo[4,3,0]nonan-7-one | 198546-12-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (1S,3R,6S)-3-hydroxy-3-(3-m-methoxyphenylpropyl)-6,8,8-trimethyl-2-oxabicyclo[4,3,0]nonan-7-one
• 英文别名: (2R,4aS,7aS)-2-hydroxy-2-[3-(3-methoxyphenyl)propyl]-4a,6,6-trimethyl-3,4,7,7a-tetrahydrocyclopenta[b]pyran-5-one
• CAS: 198546-12-2
• 化学式: C₂₁H₃₀O₄
• 分子量: 346.467
• InChiKey: HGSUDKSERFDJQB-DZFGPLHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,3R,6S)-3-hydroxy-3-(3-m-methoxyphenylpropyl)-6,8,8-trimethyl-2-oxabicyclo[4,3,0]nonan-7-one 在 chromium(VI) oxide 、 硫酸 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 0.5h， 以70%的产率得到(-)-2-(6-m-methoxyphenyl-3-oxohexyl)-2,4,4-trimethylcyclopenta-1,3-dione
  参考文献：
  名称：

  Microbial reduction of 2-(6-m-methoxyphenyl-3-oxohexyl)-2,4,4-trimethylcyclopenta-1,3-dione with Schizosaccharomyces pombe (NRRL Y-164)

  摘要：

  Racemic 2-(6-m-methoxyphenyl-3-oxohexyl)-2,4,4-trimethylcyclopenta-1,3-dione 4 was resolved by reduction with Schizosaccharomyces pombe (NRRL Y-164) to give (-)-5, (+)-6, and (+)-7 in 37, 12, and 19% yields, respectively. Chromic acid oxidation of (-)-5 gave (+)-4 while oxidation of (+)-6 and (+)-7 gave (-)-4, respectively. Sodium borohydride reduction of (+)-4 followed by Oppenauer oxidation yielded (-)-5 and (-)-7, and the same treatment of (-)-4 yielded (+)-5 and (+)-7, respectively. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00372-8
• 作为产物：
  描述：

  (1S,2R,6R)-1-hydroxy-3-(3-m-methoxyphenylpropyl)-6,8,8-trimethyl-2-oxabicyclo[4,3,0]nonan-7-one 在 chromium(VI) oxide 、 sodium tetrahydroborate 、 硫酸 、 aluminum isopropoxide 、 丙酮 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 23.5h， 生成 (1S,3R,6S)-3-hydroxy-3-(3-m-methoxyphenylpropyl)-6,8,8-trimethyl-2-oxabicyclo[4,3,0]nonan-7-one
  参考文献：
  名称：

  Microbial reduction of 2-(6-m-methoxyphenyl-3-oxohexyl)-2,4,4-trimethylcyclopenta-1,3-dione with Schizosaccharomyces pombe (NRRL Y-164)

  摘要：

  Racemic 2-(6-m-methoxyphenyl-3-oxohexyl)-2,4,4-trimethylcyclopenta-1,3-dione 4 was resolved by reduction with Schizosaccharomyces pombe (NRRL Y-164) to give (-)-5, (+)-6, and (+)-7 in 37, 12, and 19% yields, respectively. Chromic acid oxidation of (-)-5 gave (+)-4 while oxidation of (+)-6 and (+)-7 gave (-)-4, respectively. Sodium borohydride reduction of (+)-4 followed by Oppenauer oxidation yielded (-)-5 and (-)-7, and the same treatment of (-)-4 yielded (+)-5 and (+)-7, respectively. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00372-8