garuganin III | 99877-62-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: garuganin III
• 英文别名: (11E)-4,15,12-trimethoxy-2-oxatricyclo[13.2.2.1^3,7]icosa-1(17),3,5.7(20),11,15,18-heptaen-10-one；(11E)-4,5,12-trimethoxy-2-oxatricyclo[13.2.2.13,7]icosa-1(17),3,5,7(20),11,15,18-heptaen-10-one
• CAS: 99877-62-0
• 化学式: C₂₂H₂₄O₅
• 分子量: 368.43
• InChiKey: GWBKGNGQHOXUTD-XMHGGMMESA-N

物化性质

• 沸点：
  540.6±50.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  garuganin III 在 三溴化硼 作用下， 以 氯仿 为溶剂， 反应 5.0h， 以15 mg的产率得到(E)-4,5,12-Trihydroxy-2-oxa-tricyclo[13.2.2.1^3,7]icosa-1(18),3,5,7(20),11,15(19),16-heptaen-10-one
  参考文献：
  名称：

  Garuganin III，一种来自 Garuga pinnata 的大环联苯醚

  摘要：

  摘要 通过光谱分析，包括 1H NMR 和 13C NMR 解偶联实验和化学转化，确定了从 Garuga pinnata 中分离出的新型大环联苯醚 Garuganin III 的结构。

  DOI：

  10.1016/s0031-9422(00)83072-1
• 作为产物：
  描述：

  3-(Methoxycarbonyl)-5-<2-<4,5-dimethoxy-3-<4-(dimethoxymethyl)phenoxy>phenyl>-1-ethenyl>isoxazole 在 platinum(IV) oxide 、 palladium on activated charcoal 、 镍 lithium aluminium tetrahydride 、 二溴亚砜 、 potassium tert-butylate 、 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 、 苯 为溶剂， 反应 56.0h， 生成 garuganin III
  参考文献：
  名称：

  Synthesis and revised structure of garuganin III

  摘要：

  Macrocyclic beta-methoxy enones 6 and 1-3, i.e., garuganin III and its constitutional and stereoisomers, were synthesized using an isoxazole synthon for the introduction of the beta-methoxy enone function. Ring closure was accomplished by an intramolecular Wittig reaction. Compound 6 rather than 1, as suggested previously, was found to have an H-1-NMR spectrum and a mp identical to those of garuganin III.

  DOI：

  10.1021/jo00076a036

文献信息

• The Garuganin and Garugamblin Diarylether Heptanoids: Total Synthesis and Determination of Chiral Properties Using Dynamic NMR
  作者：Zhi-Qiang Zhu、M. Quamar Salih、Edward Fynn、Alex D. Bain、Christopher M. Beaudry

  DOI：10.1021/jo400157d

  日期：2013.4.5

  The synthesis of the garuganin and garugamblin diarylether heptanoids using an intramolecular Ullmann coupling is reported. Alkene stereoisomers, vinylogous ester regioisomers, and beta-diketone congeners are also synthesized. The chiral properties and free energies of activation for racemization of the garuganin and garugamblin diarylether heptanoids and congeners are determined using dynamic NMR methods. A combination of techniques including coalescence measurements, line shape analysis, and selective inversion experiments are used to measure racemization barriers. None of the garuganin or garugamblin diarylether heptanoids are chiral, despite their reported specific rotation values.
• Synthesis and revised structure of garuganin III
  作者：Gyorgy M. Keseru、Zoltan Dienes、Mihaly Nogradi、Maria Kajtar-Peredy

  DOI：10.1021/jo00076a036

  日期：1993.11

  Macrocyclic beta-methoxy enones 6 and 1-3, i.e., garuganin III and its constitutional and stereoisomers, were synthesized using an isoxazole synthon for the introduction of the beta-methoxy enone function. Ring closure was accomplished by an intramolecular Wittig reaction. Compound 6 rather than 1, as suggested previously, was found to have an H-1-NMR spectrum and a mp identical to those of garuganin III.
• Garuganin III, a macrocyclic biphenyl ether from Garuga pinnata
  作者：A.K. Mishra、M.M. Haribal、B.K. Sabata

  DOI：10.1016/s0031-9422(00)83072-1

  日期：1985.1

  Abstract The structure of garuganin III, a novel macrocyclic biphenyl ether isolated from Garuga pinnata, was established by spectroscopic analyses, including 1H NMR and 13C NMR decoupling experiments and chemical transformations

  摘要 通过光谱分析，包括 1H NMR 和 13C NMR 解偶联实验和化学转化，确定了从 Garuga pinnata 中分离出的新型大环联苯醚 Garuganin III 的结构。