garugamblin-1

• 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: garugamblin-1
• 英文别名: garugamblin I；Alqfmxsftoufst-xmhggmmesa-；(11E)-4,12-dimethoxy-2-oxatricyclo[13.2.2.13,7]icosa-1(17),3,5,7(20),11,15,18-heptaen-10-one
• 化学式: C₂₁H₂₂O₄
• 分子量: 338.403
• InChiKey: ALQFMXSFTOUFST-XMHGGMMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-(4-溴苯基)丁烷-2-酮 在 吡啶 、 正丁基锂 、 五甲基苯 、 三氯化硼 、 potassium carbonate 、 对甲苯磺酸 、 二异丙胺 、 copper(II) oxide 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 99.67h， 生成 garugamblin-1
  参考文献：
  名称：

  The Garuganin and Garugamblin Diarylether Heptanoids: Total Synthesis and Determination of Chiral Properties Using Dynamic NMR

  摘要：

  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.

  DOI：

  10.1021/jo400157d

文献信息

• The synthesis of garugamblin-1
  作者：Borbála Vermes、György M. Keserû、Gabriella Mezey-Vándor、Mihály Nógrádix、Gábor Tóth

  DOI：10.1016/s0040-4020(01)80406-3

  日期：1993.5

  The Z isomer of the title compound (21) and its regioisomer (22) were synthesized using an isoxazole synthon (17) for the elaboration of the beta-methoxy-enone function. 21 and 20 spontaneously isomerized to the E isomers i.e. to garugamblin-1 (1) and its regioisomer (22) resp.
• 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.