Methyl 2-hydroxy-3-(2-hydroxy-5,6-dimethoxy-3-methoxycarbonyl-4-methylphenyl)-4,5-dimethoxy-6-methylbenzoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Methyl 2-hydroxy-3-(2-hydroxy-5,6-dimethoxy-3-methoxycarbonyl-4-methylphenyl)-4,5-dimethoxy-6-methylbenzoate
• 英文别名: methyl 2-hydroxy-3-(2-hydroxy-5,6-dimethoxy-3-methoxycarbonyl-4-methylphenyl)-4,5-dimethoxy-6-methylbenzoate
• 化学式: C₂₂H₂₆O₁₀
• 分子量: 450.442
• InChiKey: BOQGJIYGZXLXFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Methyl 2-hydroxy-3-(2-hydroxy-5,6-dimethoxy-3-methoxycarbonyl-4-methylphenyl)-4,5-dimethoxy-6-methylbenzoate 在 吡啶 、 1,3-二溴-5,5-二甲基海因 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 4.5h， 生成 dimethyl 2,2'-bis(benzoyloxy)-4,4'-bis(bromomethyl)-5,5',6,6'-tetramethoxy-[1,1'-biphenyl]-3,3'-dicarboxylate
  参考文献：
  名称：

  The first total synthesis of hibarimicinone, a potent v-Src tyrosine kinase inhibitor

  摘要：

  The first total synthesis of hibarimicinone has been achieved. The polyhydroxydecalin moieties (AB and GH rings) have been synthesized from sulfonylenone 4 derived from D-arabinose. The chiral biaryl 20 was coupled with two polyhydroxydecalins 11 by Michael-Dieckmann type condensation to give the eight rings system. Aromatization and oxidation with Ag+ gave quinone 24, and the subsequential transannular etheration gave the hibarimicinone skeleton. Deprotection and tautomerization were performed in one pot to give hibarimicinone (1). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.062
• 作为产物：
  描述：

  2,4,5-三甲氧基苯甲酸 在 disodium hydrogenphosphate 、 四甲基乙二胺 、 仲丁基锂 、 silver trifluoroacetate 、 三甲基乙酰氯 、 三氯化硼 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 32.17h， 生成 Methyl 2-hydroxy-3-(2-hydroxy-5,6-dimethoxy-3-methoxycarbonyl-4-methylphenyl)-4,5-dimethoxy-6-methylbenzoate
  参考文献：
  名称：

  The first total synthesis of hibarimicinone, a potent v-Src tyrosine kinase inhibitor

  摘要：

  The first total synthesis of hibarimicinone has been achieved. The polyhydroxydecalin moieties (AB and GH rings) have been synthesized from sulfonylenone 4 derived from D-arabinose. The chiral biaryl 20 was coupled with two polyhydroxydecalins 11 by Michael-Dieckmann type condensation to give the eight rings system. Aromatization and oxidation with Ag+ gave quinone 24, and the subsequential transannular etheration gave the hibarimicinone skeleton. Deprotection and tautomerization were performed in one pot to give hibarimicinone (1). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.062

文献信息

• Synthetic Studies on the Bis-Anthraquinoid Core of the Angelimicins
  作者：David Mootoo、Jialiang Li

  DOI：10.1055/s-0033-1339281

  日期：——

  Bidirectional Hauser and Michael-Dieckmann annulation strategies for the preparation of bis-anthraquinoid framework of the angelimicin family of natural products are explored, using cyclohex-2-enone and biphenyl Michael donors, which are prepared from 1,2,5-trimethoxy-3-methylbenzene. The Hauser annulations are not productive, but the Michael-Dieckmann reactions proceed in 40% yield. Attempts to aromatize these biphenyl cycloadducts proved unsuccessful. This result differs from the success reported in another study of the same reaction. In contrast, aromatization of the related monomeric Michael-Dieckmann cycloadduct proceeds smoothly.
• The first total synthesis of hibarimicinone, a potent v-Src tyrosine kinase inhibitor
  作者：Kuniaki Tatsuta、Tomohiro Fukuda、Tatsuya Ishimori、Rearu Yachi、Shinpei Yoshida、Hiroshi Hashimoto、Seijiro Hosokawa

  DOI：10.1016/j.tetlet.2011.11.062

  日期：2012.1

  The first total synthesis of hibarimicinone has been achieved. The polyhydroxydecalin moieties (AB and GH rings) have been synthesized from sulfonylenone 4 derived from D-arabinose. The chiral biaryl 20 was coupled with two polyhydroxydecalins 11 by Michael-Dieckmann type condensation to give the eight rings system. Aromatization and oxidation with Ag+ gave quinone 24, and the subsequential transannular etheration gave the hibarimicinone skeleton. Deprotection and tautomerization were performed in one pot to give hibarimicinone (1). (C) 2011 Elsevier Ltd. All rights reserved.