rac. Octa-O-methyl-valoneasaeure | 117776-69-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: rac. Octa-O-methyl-valoneasaeure
• 英文别名: (+/-)-4-(6-carboxy-2,3,4-trimethoxy-phenoxy)-5,6,4',5',6'-pentamethoxy-diphenic acid；(+/-)-4-(6-Carboxy-2,3,4-trimethoxy-phenoxy)-5,6,4',5',6'-pentamethoxy-diphensaeure；2-[6-Carboxy-4-(6-carboxy-2,3,4-trimethoxyphenoxy)-2,3-dimethoxyphenyl]-3,4,5-trimethoxybenzoic acid；2-[6-carboxy-4-(6-carboxy-2,3,4-trimethoxyphenoxy)-2,3-dimethoxyphenyl]-3,4,5-trimethoxybenzoic acid
• CAS: 117776-69-9
• 化学式: C₂₉H₃₀O₁₅
• 分子量: 618.548
• InChiKey: LKSPGAFXZXYCLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  44
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  195
• 氢给体数：
  3
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  三甲基硅烷化重氮甲烷 、 rac. Octa-O-methyl-valoneasaeure 以 甲醇 为溶剂， 反应 24.0h， 以63 mg的产率得到(S)-6,6'-dimethyl-4-(6-methoxycarbonyl-2,3,4-trimethoxyphenoxy)-2,2',3,3',4'-pentamethoxy-1,1'-biphenyl dicarboxylate
  参考文献：
  名称：

  Syntheses of all-methylated ellagitannin, isorugosin B and rugosin B

  摘要：

  Ellagitannins possess a wide range of biological activities and remarkable structural diversity, which commonly include an axially chiral biaryl unit. This paper describes syntheses of all-methylated versions of isorugosin B and rugosin B, which are regioisomeric, ellagitannin-related compounds. The key features of these syntheses involve the construction of an axially chiral biaryl function on a sugar moiety through a Pd-catalyzed intramolecular biaryl coupling reaction, Bringmann's atroposelective lactone opening reaction, and a two-step ester formation. This is the first synthetic approach for generating ellagitannins featuring a valoneoyl group. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.004
• 作为产物：
  描述：

  3,4,5-trimethoxy-2-(3,7,8-trimethoxy-5,10-dioxo-5,10-dihydro-chromeno[5,4,3-cde]chromen-2-yloxy)-benzoic acid methyl ester 在 sodium hydroxide 作用下， 生成 rac. Octa-O-methyl-valoneasaeure
  参考文献：
  名称：

  Schmidt; Komarek, Justus Liebigs Annalen der Chemie, 1955, vol. 591, p. 156,170

  摘要：

  DOI：

文献信息

• Schmidt et al., Justus Liebigs Annalen der Chemie, 1957, vol. 602, p. 50,58
  作者：Schmidt et al.

  DOI：——

  日期：——
• Schmidt; Komarek, Justus Liebigs Annalen der Chemie, 1955, vol. 591, p. 156,170
  作者：Schmidt、Komarek

  DOI：——

  日期：——
• Syntheses of all-methylated ellagitannin, isorugosin B and rugosin B
  作者：Kazuma Shioe、Yusuke Sahara、Yoshikazu Horino、Takashi Harayama、Yasuo Takeuchi、Hitoshi Abe

  DOI：10.1016/j.tet.2011.01.004

  日期：2011.3

  Ellagitannins possess a wide range of biological activities and remarkable structural diversity, which commonly include an axially chiral biaryl unit. This paper describes syntheses of all-methylated versions of isorugosin B and rugosin B, which are regioisomeric, ellagitannin-related compounds. The key features of these syntheses involve the construction of an axially chiral biaryl function on a sugar moiety through a Pd-catalyzed intramolecular biaryl coupling reaction, Bringmann's atroposelective lactone opening reaction, and a two-step ester formation. This is the first synthetic approach for generating ellagitannins featuring a valoneoyl group. (C) 2011 Elsevier Ltd. All rights reserved.