1-(4-bromophenyl)-7-(7-hydroxybenzo[d][1,3]dioxol-5-yl)heptane-3,5-dione | 1426838-50-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 1-(4-bromophenyl)-7-(7-hydroxybenzo[d][1,3]dioxol-5-yl)heptane-3,5-dione
• 英文别名: 1-(4-Bromophenyl)-7-(7-hydroxy-1,3-benzodioxol-5-yl)heptane-3,5-dione；1-(4-bromophenyl)-7-(7-hydroxy-1,3-benzodioxol-5-yl)heptane-3,5-dione
• CAS: 1426838-50-7
• 化学式: C₂₀H₁₉BrO₅
• 分子量: 419.272
• InChiKey: RKJJEYAKHNGLOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(4-bromophenyl)-7-(7-hydroxybenzo[d][1,3]dioxol-5-yl)heptane-3,5-dione 在 吡啶 、 potassium carbonate 、 copper(II) oxide 作用下， 反应 24.0h， 以38%的产率得到
  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
• 作为产物：
  描述：

  3-benzyloxy-4,5-methylendioxybenzaldehyde 在 正丁基锂 、 五甲基苯 、 sodium acetate 、 三氯化硼 、 sodium hydride 、 二异丁基氢化铝 、 二异丙胺 、 对甲苯磺酰肼 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 反应 28.59h， 生成 1-(4-bromophenyl)-7-(7-hydroxybenzo[d][1,3]dioxol-5-yl)heptane-3,5-dione
  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 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.