dimethyl 2,2',5,5',6,6'-hexamethoxy-4,4'-dimethyl-[1,1'-biphenyl]-3,3'-dicarboxylate | 1462393-85-6

• 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: dimethyl 2,2',5,5',6,6'-hexamethoxy-4,4'-dimethyl-[1,1'-biphenyl]-3,3'-dicarboxylate
• 英文别名: Methyl 2,4,5-trimethoxy-6-methyl-3-(2,3,6-trimethoxy-5-methoxycarbonyl-4-methylphenyl)benzoate；methyl 2,4,5-trimethoxy-6-methyl-3-(2,3,6-trimethoxy-5-methoxycarbonyl-4-methylphenyl)benzoate
• CAS: 1462393-85-6
• 化学式: C₂₄H₃₀O₁₀
• 分子量: 478.496
• InChiKey: IMKJQANSJPDFPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  dimethyl 2,2',5,5',6,6'-hexamethoxy-4,4'-dimethyl-[1,1'-biphenyl]-3,3'-dicarboxylate 在 三氯化硼 、 N,N-二异丙基乙胺 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 4.17h， 生成 dimethyl 5,5',6,6'-tetramethoxy-2,2'-bis(methoxymethoxy)-4,4'-dimethyl-[1,1'-biphenyl]-3,3'-dicarboxylate
  参考文献：
  名称：

  Synthetic Studies on the Bis-Anthraquinoid Core of the Angelimicins

  摘要：

  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.

  DOI：

  10.1055/s-0033-1339281
• 作为产物：
  描述：

  2,2',3,3',6,6'-hexamethoxy-4,4'-dimethyl-1,1'-biphenyl 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2,3-二甲基-2-丁烯 、 双氧水 、 四氯化钛 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 6.0h， 生成 dimethyl 2,2',5,5',6,6'-hexamethoxy-4,4'-dimethyl-[1,1'-biphenyl]-3,3'-dicarboxylate
  参考文献：
  名称：

  Synthetic Studies on the Bis-Anthraquinoid Core of the Angelimicins

  摘要：

  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.

  DOI：

  10.1055/s-0033-1339281

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.