2-(2-bromo-3,4,5-trimethoxyphenyl)-1,3-dioxane | 130611-32-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(2-bromo-3,4,5-trimethoxyphenyl)-1,3-dioxane
• 英文别名: 2-(2-Bromo-3,4,5-trimethoxyphenyl)-1,3-dioxane
• CAS: 130611-32-4
• 化学式: C₁₃H₁₇BrO₅
• 分子量: 333.179
• InChiKey: AOBMQHOSHMOLJR-UHFFFAOYSA-N

物化性质

• 沸点：
  373.2±42.0 °C(Predicted)
• 密度：
  1.382±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2-bromo-3,4,5-trimethoxyphenyl)-1,3-dioxane 在 ruthenium trichloride 、 sodium tetrahydroborate 、 copper(l) iodide 、 四(三苯基膦)钯 、 正丁基锂 、 potassium metaperiodate 、 碘 、 silver trifluoroacetate 、 三溴化磷 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 氯仿 、 水 、 乙腈 为溶剂， 反应 21.5h， 生成 1,2-bis(2-(bromomethyl)-4,5,6-trimethoxy-3-methylphenyl)ethan-1,2-dione
  参考文献：
  名称：

  Eleganketal A, a Highly Oxygenated Dibenzospiroketal from the Marine-Derived Fungus Spicaria elegans KLA03

  摘要：

  Eleganketal A (1), a naturally occurring aromatic polyketide possessing a rare highly oxygenated spiro[isobenzofuran-1,3'-isochroman] ring system, was isolated from the fungus Spicaria elegans KLA03 by culturing it in a modified mannitol-based medium. The structure of 1 including the absolute configuration was determined by combining spectroscopic analysis, synthesis of the racemic permethylated analogue, chiral-phase HPLC separation, and TDDFT-ECD analysis.

  DOI：

  10.1021/np500458a
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 在 溴 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 24.5h， 生成 2-(2-bromo-3,4,5-trimethoxyphenyl)-1,3-dioxane
  参考文献：
  名称：

  Eleganketal A, a Highly Oxygenated Dibenzospiroketal from the Marine-Derived Fungus Spicaria elegans KLA03

  摘要：

  Eleganketal A (1), a naturally occurring aromatic polyketide possessing a rare highly oxygenated spiro[isobenzofuran-1,3'-isochroman] ring system, was isolated from the fungus Spicaria elegans KLA03 by culturing it in a modified mannitol-based medium. The structure of 1 including the absolute configuration was determined by combining spectroscopic analysis, synthesis of the racemic permethylated analogue, chiral-phase HPLC separation, and TDDFT-ECD analysis.

  DOI：

  10.1021/np500458a

文献信息

• Asymmetric total synthesis of dibenzocyclooctadiene lignans (-)-schizandrin and (-)-isoschizandrin. Structure revision of (+)-isoschizandrin
  作者：Alan M. Warshawsky、A. I. Meyers

  DOI：10.1021/ja00178a037

  日期：1990.10

  The oxazoline-mediated biaryl coupling reaction was applied successfully to the total synthesis of a series of dibenzocyclooctadiene lignans in chiral nonracemic form. The diastereoselectivities achieved in the coupling reaction varied in a predictable manner, primarily as a function of the ortho substituents on the phenyl Grignard reagent

  恶唑啉介导的联芳基偶联反应成功地应用于一系列手性非外消旋形式的二苯并环辛二烯木脂素的全合成。偶联反应中实现的非对映选择性以可预测的方式变化，主要取决于苯基格氏试剂上的邻位取代基
• First Asymmetric Synthesis of (Un)saturated 1-Alkylbenzo[<i>c</i>]azepin-3-ones: Extension to the Corresponding Benzazepines
  作者：David Dumoulin、Stéphane Lebrun、Eric Deniau、Axel Couture、Pierre Grandclaudon

  DOI：10.1002/ejoc.200900365

  日期：2009.8

  A flexible route for the stereoselective synthesis of a variety of structurally diverse (1R)-1-alkyldihydro and tetrahydrobenzazepin(ones) has been developed. The key step is a highly diastereoselective 1,2-addition process applied to a stereopure aromatic hydrazone combined with a ring-closing metathesis reaction to secure the formation of the seven-membered azaheterocycle ring system.(© Wiley-VCH

  已经开发了用于立体选择性合成各种结构不同的 (1R)-1-烷基二氢和四氢苯并氮杂的灵活路线。关键步骤是将高度非对映选择性 1,2-加成过程应用于立体纯芳香腙结合闭环复分解反应以确保形成七元氮杂杂环系统。 (© Wiley-VCH Verlag GmbH & Co. KGaA，69451 魏因海姆，德国，2009）
• Eleganketal A, a Highly Oxygenated Dibenzospiroketal from the Marine-Derived Fungus <i>Spicaria elegans</i> KLA03
  作者：Yepeng Luan、Hongjuan Wei、Zhenpei Zhang、Qian Che、Yankai Liu、Tianjiao Zhu、Attila Mándi、Tibor Kurtán、Qianqun Gu、Dehai Li

  DOI：10.1021/np500458a

  日期：2014.7.25

  Eleganketal A (1), a naturally occurring aromatic polyketide possessing a rare highly oxygenated spiro[isobenzofuran-1,3'-isochroman] ring system, was isolated from the fungus Spicaria elegans KLA03 by culturing it in a modified mannitol-based medium. The structure of 1 including the absolute configuration was determined by combining spectroscopic analysis, synthesis of the racemic permethylated analogue, chiral-phase HPLC separation, and TDDFT-ECD analysis.