dimethyl 2,2'-bis(benzoyloxy)-4,4'-bis(bromomethyl)-5,5',6,6'-tetramethoxy-[1,1'-biphenyl]-3,3'-dicarboxylate | 1354785-00-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: dimethyl 2,2'-bis(benzoyloxy)-4,4'-bis(bromomethyl)-5,5',6,6'-tetramethoxy-[1,1'-biphenyl]-3,3'-dicarboxylate
• CAS: 1354785-00-4
• 化学式: C₃₆H₃₂Br₂O₁₂
• 分子量: 816.451
• InChiKey: FWUQPENRNBETGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.19
• 重原子数：
  50.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  142.12
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  dimethyl 2,2'-bis(benzoyloxy)-4,4'-bis(bromomethyl)-5,5',6,6'-tetramethoxy-[1,1'-biphenyl]-3,3'-dicarboxylate 在 甲醇 、 sodium methylate 、 三乙胺 、 potassium thioacetate 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 2.0h， 生成 C₂₀H₁₈O₈S₂
  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 吡啶 、 disodium hydrogenphosphate 、 1,3-二溴-5,5-二甲基海因 、 偶氮二异丁腈 、 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 、 四氯化碳 、 二氯甲烷 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 36.67h， 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