(+/-)-rel-(1R,2S,6R,7R)-11-oxo-1-trifluoromethyl-8,10-dioxa-tricyclo<5.4.0.0^2,6>undecane-9-spirocyclohexane | 142779-91-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-rel-(1R,2S,6R,7R)-11-oxo-1-trifluoromethyl-8,10-dioxa-tricyclo<5.4.0.0^2,6>undecane-9-spirocyclohexane
• 英文别名: (1R,2S,6R,7R)-1-(trifluoromethyl)spiro[8,10-dioxatricyclo[5.4.0.02,6]undecane-9,1'-cyclohexane]-11-one
• CAS: 142779-91-7；142797-16-8
• 化学式: C₁₅H₁₉F₃O₃
• 分子量: 304.309
• InChiKey: LTFKIRPCPJDHTM-FBKDDSFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-iodo-4-oxo-4H-1,3-dioxine-2-spirocyclohexane 在 铜 作用下， 以 乙酸乙酯 、 苯 为溶剂， 反应 6.0h， 生成 (+/-)-rel-(1R,2S,6R,7R)-11-oxo-1-trifluoromethyl-8,10-dioxa-tricyclo<5.4.0.0^2,6>undecane-9-spirocyclohexane
  参考文献：
  名称：

  Iwaoka, Tomoyasu; Murohashi, Tomoko; Katagiri, Nobuya, Journal of the Chemical Society. Perkin transactions I, 1992, # 11, p. 1393 - 1398

  摘要：

  DOI：

文献信息

• Use of 1,3-Dioxin-4-ones and Related Compounds in Synthesis. XXXVIII. Use of 1,3-Dioxin-4-ones Having a Fluorine or Trifluoromethyl Group at the 5-Position as .PI.2 Components in (2+2)-Photocycloaddition and Diels-Alder Reactions.
  作者：Tomoyasu IWAOKA、Nobuya KATAGIRI、Masayuki SATO、Chikara KANEKO

  DOI：10.1248/cpb.40.2319

  日期：——

  1, 3-Dioxin-4-ones having fluorine or a trifluoromethyl group at the 5-position were used as the π2 components in Diels-Alder reactions with 1-oxygenated dienes. Use of high-perssure conditions was the essential requisite. While the 5-flurodioxinones were photolabile, the corresponding trifluoromethyl derivatives participated as the enone components in [2+2]photocycloaddition to alkenes, Ring-opening reactions of these adducts by acetal bond cleavage gave cyclobutanes and cyclohexanes. Diels-Alder reactions of the fluorinated homochiral dioxinones having l-menthone at the acetal position with Danishefsky diene proceeded in a completely diastereoselective manner to give single adducts.

  在Diels-Alder反应中，1,3-二噁烷-4-酮在5位含氟或三氟甲基基团的化合物被用作π2组分，与1-氧化的二烯反应。使用高压条件是必要的要求。虽然5-氟二噁烷酮是光敏的，但相应的三氟甲基衍生物作为enone组分参与与烯烃的[2+2]光环加成。这些加合物通过缩醛键断裂的开环反应生成环丁烷和环己烷。具有l-薄荷酮作为缩醛位置的氟化手性二噁烷酮与Danishefsky二烯的Diels-Alder反应以完全的非对映选择性进行，给出单一的加合物。
• Iwaoka Tomoyasu, Katagiri Nobuya, Sato Masayuki, Kaneko Chikara, Chem. and Pharm. Bull., 40 (1992) N 9, S 2319-2324
  作者：Iwaoka Tomoyasu, Katagiri Nobuya, Sato Masayuki, Kaneko Chikara

  DOI：——

  日期：——