OSe-((1R,3R,4R,6S)-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]heptan-3-yl) trifluoromethanesulfono(selenoperoxoate) | 1215291-16-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: OSe-((1R,3R,4R,6S)-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]heptan-3-yl) trifluoromethanesulfono(selenoperoxoate)
• CAS: 1215291-16-9
• 化学式: C₁₁H₁₇F₃O₄SSe
• 分子量: 381.275
• InChiKey: SBDWJYOOORDOOP-IBCQBUCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.08
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  苯乙烯 、 甲醇 、 OSe-((1R,3R,4R,6S)-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]heptan-3-yl) trifluoromethanesulfono(selenoperoxoate) 以 二氯甲烷 为溶剂， 以54%的产率得到[(1S,3R)-3-hydroxy-4-isocaranyl] (2-methoxy-2-phenylethyl) selenide
  参考文献：
  名称：

  Syntheses and reactions of terpene β-hydroxyselenides and β-hydroxydiselenides

  摘要：

  A convenient method for the synthesis of optically active trans-hydroxyselenides and trans-hydroxydiselenides from the bicyclic terpene group based on the reactions of sodium selenide or sodium diselenide with cis- and trans-(+)-3-carane, trans-(+)-2-carane and (-)-beta-pinane epoxides is described. The corresponding cis-hydroxy and cis-methoxydiselenides were obtained in the reaction of sodium diselenide with beta-hydroxy- and beta-methoxytosylates. The influence of a hydroxy group at the beta-position on the diastereomeric ratio of the products of the asymmetric methoxyselenenylation of styrene has been established by composition of the products, crystal structure analyses, and theoretical calculations using a DFT method on the B3LYP level (6-311G(d)). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.12.001
• 作为产物：
  描述：

  (1S,3R,4R,6R)-4-[[(1R,3R,4R,6S)-4-hydroxy-4,7,7-trimethyl-3-bicyclo[4.1.0]heptanyl]diselanyl]-3,7,7-trimethylbicyclo[4.1.0]heptan-3-ol 、 silver trifluoromethanesulfonate 在 溴 作用下， 以 四氯化碳 、 甲醇 、 二氯甲烷 为溶剂， 生成 OSe-((1R,3R,4R,6S)-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]heptan-3-yl) trifluoromethanesulfono(selenoperoxoate)
  参考文献：
  名称：

  Syntheses and reactions of terpene β-hydroxyselenides and β-hydroxydiselenides

  摘要：

  A convenient method for the synthesis of optically active trans-hydroxyselenides and trans-hydroxydiselenides from the bicyclic terpene group based on the reactions of sodium selenide or sodium diselenide with cis- and trans-(+)-3-carane, trans-(+)-2-carane and (-)-beta-pinane epoxides is described. The corresponding cis-hydroxy and cis-methoxydiselenides were obtained in the reaction of sodium diselenide with beta-hydroxy- and beta-methoxytosylates. The influence of a hydroxy group at the beta-position on the diastereomeric ratio of the products of the asymmetric methoxyselenenylation of styrene has been established by composition of the products, crystal structure analyses, and theoretical calculations using a DFT method on the B3LYP level (6-311G(d)). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.12.001