(2R,3R)-6-((R)-4-Hydroxy-1,1,3-trimethyl-butyl)-2-isopropyl-3-methyl-2,3-dihydro-pyran-4-one | 136320-75-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2R,3R)-6-((R)-4-Hydroxy-1,1,3-trimethyl-butyl)-2-isopropyl-3-methyl-2,3-dihydro-pyran-4-one
• CAS: 136320-75-7
• 化学式: C₁₆H₂₈O₃
• 分子量: 268.397
• InChiKey: JMLCQQFQTHTLRA-TYNCELHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 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：

  (2R,3R)-6-((R)-4-Hydroxy-1,1,3-trimethyl-butyl)-2-isopropyl-3-methyl-2,3-dihydro-pyran-4-one 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 (2R,3R,6S,7R,9R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-isopropyl-3,9,11,11-tetramethyl-8-oxo-1-oxa-spiro[5.5]undec-4-ene-7-carboxylic acid 2-trimethylsilanyl-ethyl ester
  参考文献：
  名称：

  A stereoselective route to the spirobicyclic ring system of oscillatoxin D

  摘要：

  Using a model system, a stereoselective assembly of the 1-oxaspiro[5.5]undec-4-ene-8-one ring system of the antileukemic natural products oscillatoxin D and 30-methyloscillatoxin D was demonstrated. A key step was an intramolecular attack of the C1-C3 beta-ketoester enol on a silyl-activated 2,3-dihydro-4-pyranone to create a silyloxy analogue of the natural product's spirobicyclic ring system.

  DOI：

  10.1016/0040-4039(91)80594-v
• 作为产物：
  描述：

  (2R,8S,9R)-7-hydroxy-1-[(4-methoxyphenyl)methoxy]-2,4,4,8,10-pentamethyl-9-phenylmethoxyundecan-5-one 在 W-2 Raney Ni 氢气 、 三乙胺 、 (1S)-7,7-dimethyl-2-oxo-1-bicyclo[2.2.1]heptanesulfonic acid 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 27.17h， 生成 (2R,3R)-6-((R)-4-Hydroxy-1,1,3-trimethyl-butyl)-2-isopropyl-3-methyl-2,3-dihydro-pyran-4-one
  参考文献：
  名称：

  A stereoselective route to the spirobicyclic ring system of oscillatoxin D

  摘要：

  Using a model system, a stereoselective assembly of the 1-oxaspiro[5.5]undec-4-ene-8-one ring system of the antileukemic natural products oscillatoxin D and 30-methyloscillatoxin D was demonstrated. A key step was an intramolecular attack of the C1-C3 beta-ketoester enol on a silyl-activated 2,3-dihydro-4-pyranone to create a silyloxy analogue of the natural product's spirobicyclic ring system.

  DOI：

  10.1016/0040-4039(91)80594-v