(E)-((R)-((4R,4aR,8aS)-2,2-dimethyl-6-oxo-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxin-4-yl)(phenyl)methyl) 4,4,4-trifluorobut-2-enoate | 1234064-06-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: (E)-((R)-((4R,4aR,8aS)-2,2-dimethyl-6-oxo-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxin-4-yl)(phenyl)methyl) 4,4,4-trifluorobut-2-enoate
• 英文别名: [(R)-[(4R,4aR,8aS)-2,2-dimethyl-6-oxo-4a,8a-dihydro-4H-pyrano[3,2-d][1,3]dioxin-4-yl]-phenylmethyl] (E)-4,4,4-trifluorobut-2-enoate
• CAS: 1234064-06-2
• 化学式: C₂₀H₁₉F₃O₆
• 分子量: 412.362
• InChiKey: VHONBRJKWBPXLF-GTSYHYIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (E)-((R)-((4R,4aR,8aS)-2,2-dimethyl-6-oxo-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxin-4-yl)(phenyl)methyl) 4,4,4-trifluorobut-2-enoate 在 水 、 溶剂黄146 作用下， 反应 3.0h， 以57%的产率得到(E)-((1R,2R)-2-hydroxy-2-((2R,3S)-3-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-phenylethyl) 4,4,4-trifluorobut-2-enoate
  参考文献：
  名称：

  Synthesis and cytotoxic activity of fluorinated analogues of Goniothalamus lactones. Impact of fluorine on oxidative processes

  摘要：

  Novel fluorinated analogues of goniothalamin 1 and howiinol A 2 have been prepared from trifluorocrotonate derivatives. Trifluoromethyl goniothalamin (R/S) 4 showed a slightly lower activity than 1, while the trifluoromethyl howiinol A 16 exhibited similar activities on several cell lines in the micromolar range. Unlike (R) goniothalamin and howiinol A, trifluoromethyl parent compounds remained unchanged when submitted to biomimetic oxidative systems. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.03.032
• 作为产物：
  描述：

  4,4,4-三氟丁-2-烯酸 、 4,6-O-Isopropylidene-7-C-phenyl-D-gluco-hept-2-enono-δ-lactone 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以94%的产率得到(E)-((R)-((4R,4aR,8aS)-2,2-dimethyl-6-oxo-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxin-4-yl)(phenyl)methyl) 4,4,4-trifluorobut-2-enoate
  参考文献：
  名称：

  Synthesis and cytotoxic activity of fluorinated analogues of Goniothalamus lactones. Impact of fluorine on oxidative processes

  摘要：

  Novel fluorinated analogues of goniothalamin 1 and howiinol A 2 have been prepared from trifluorocrotonate derivatives. Trifluoromethyl goniothalamin (R/S) 4 showed a slightly lower activity than 1, while the trifluoromethyl howiinol A 16 exhibited similar activities on several cell lines in the micromolar range. Unlike (R) goniothalamin and howiinol A, trifluoromethyl parent compounds remained unchanged when submitted to biomimetic oxidative systems. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.03.032

文献信息

• Synthesis and cytotoxic activity of fluorinated analogues of Goniothalamus lactones. Impact of fluorine on oxidative processes
  作者：Lidia Dumitrescu、Doan Thi Mai Huong、Nguyen Van Hung、Benoit Crousse、Danièle Bonnet-Delpon

  DOI：10.1016/j.ejmech.2010.03.032

  日期：2010.7

  Novel fluorinated analogues of goniothalamin 1 and howiinol A 2 have been prepared from trifluorocrotonate derivatives. Trifluoromethyl goniothalamin (R/S) 4 showed a slightly lower activity than 1, while the trifluoromethyl howiinol A 16 exhibited similar activities on several cell lines in the micromolar range. Unlike (R) goniothalamin and howiinol A, trifluoromethyl parent compounds remained unchanged when submitted to biomimetic oxidative systems. (C) 2010 Elsevier Masson SAS. All rights reserved.