(1R,3R,4R,5S,8R)-1-(4-bromophenyl)-5-isopropyl-8-methyl-3-spiro[2.5]octan-4,5-diole | 1383783-20-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,3R,4R,5S,8R)-1-(4-bromophenyl)-5-isopropyl-8-methyl-3-spiro[2.5]octan-4,5-diole
• CAS: 1383783-20-7
• 化学式: C₁₈H₂₅BrO₂
• 分子量: 353.299
• InChiKey: UWMAXFXFORZHIH-YXWSMURKSA-N

反应信息

• 作为产物：
  描述：

  (1R,5S,8R,3R)-1-(4-bromophenyl)-5-isopropyl-5-hydroxy-8-methyl-3-spiro[2.5]octan-4-one 在 sodium tetrahydroborate 作用下， 以 异丙醇 为溶剂， 以62%的产率得到(1R,3R,4R,5S,8R)-1-(4-bromophenyl)-5-isopropyl-8-methyl-3-spiro[2.5]octan-4,5-diole
  参考文献：
  名称：

  Stereochemistry of hydroxylation of some chiral spiro-[2,5]octan-4-ones

  摘要：

  Stereoselective oxidative alpha hydroxylation of (1R,5R,8R,3R)-1-aryl-5-isopropyl-8-methyl-3-spiro-[2,5,]octan-4-ones has been found as a secondary process in the cyclopropanation of 2-arylidene isomenthanones with trimethylsulfoxonium iodide in DMSO/NaOH or DMF/NaOH system. Three stereoisomeric hydroxy ketones have been isolated from a reaction mixture of cyclopropanation reaction, but the reaction of oxidation carried out with isolated spiro-[2,5]octan-4-ones was stereoselective. The advantages of this method of stereoselective hydroxylation are room temperature of reaction and absence of expensive catalysts. The reduction of obtained hydroxy ketones was also stereoselective and gave the only trans-7 (4,5S)-dioles. The structures have been confirmed with 1D and 2D H-1 and C-13 NMR, MS spectra and for stereoisomeric hydroxy ketones with X-ray analysis also. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2012.03.052