(-)-9-tert-butyl-2S-ethyl-1,4-dioxaspiro[4.(5S)]deca-7,9-dien-6-one | 1038436-78-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-9-tert-butyl-2S-ethyl-1,4-dioxaspiro[4.(5S)]deca-7,9-dien-6-one
• 英文别名: (3S,5S)-9-tert-butyl-3-ethyl-1,4-dioxaspiro[4.5]deca-7,9-dien-6-one
• CAS: 1038436-78-0
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: RHEGQCOAVQLPTL-FZMZJTMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (S)-(+)-2-(2-hydroxybutoxy)-4-tert-butylphenol 在 碘苯二乙酸 作用下， 以 2,2,2-三氟乙醇 为溶剂， 反应 0.42h， 生成 9-tert-butyl-2S-ethyl-1,4-dioxaspiro[4.(5R)]deca-7,9-dien-6-one 、 (-)-9-tert-butyl-2S-ethyl-1,4-dioxaspiro[4.(5S)]deca-7,9-dien-6-one
  参考文献：
  名称：

  Hypervalent iodine-mediated oxygenative phenol dearomatization reactions

  摘要：

  Both lambda(3)- and lambda(5)-iodanes have proven to be useful reagents in the oxygenative dearomatization of phenols, and exploitations of their chemistry in the conception of both substrate- and reagent-controlled asymmetric variants of such a transformation of great value for natural product synthesis have shown evident signs of success. Moreover, the use of stabilized IBX (i.e., SIBX) in our methodology for O-demethylation of 2-methoxyphenols, which relies on the same key oxygenating dearomatization event, is reported here to be much more efficacious than that of 1BX itself in the chemoselective one-step conversion of homovanillyl alcohol into hydroxytyrosol, and bergenin into norbergenin. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.05.078

文献信息

• Highly Diastereoselective Synthesis of Orthoquinone Monoketals through λ3-Iodane-Mediated Oxidative Dearomatization of Phenols
  作者：Laurent Pouységu、Stefan Chassaing、Delphine Dejugnac、Anne-Marie Lamidey、Karinne Miqueu、Jean-Marc Sotiropoulos、Stéphane Quideau

  DOI：10.1002/anie.200705816

  日期：2008.4.28