1-acetoxymethyl-3-(6-acetoxymethyl-2,3,4-trimethoxyphenoxy)-4,8,9,10-tetramethoxydibenzo[b,d]pyran-6-one | 1010094-09-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: 1-acetoxymethyl-3-(6-acetoxymethyl-2,3,4-trimethoxyphenoxy)-4,8,9,10-tetramethoxydibenzo[b,d]pyran-6-one
• 英文别名: [3-[6-(Acetyloxymethyl)-2,3,4-trimethoxyphenoxy]-4,8,9,10-tetramethoxy-6-oxobenzo[c]chromen-1-yl]methyl acetate
• CAS: 1010094-09-3
• 化学式: C₃₂H₃₄O₁₄
• 分子量: 642.614
• InChiKey: OWBDJDWXIGOIJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  46
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  153
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  1-acetoxymethyl-3-(6-acetoxymethyl-2,3,4-trimethoxyphenoxy)-4,8,9,10-tetramethoxydibenzo[b,d]pyran-6-one 在 sodium chlorite 、 lithium aluminium tetrahydride 、 Jones reagent 、 硼烷四氢呋喃络合物 、 potassium tert-butylate 、 双氧水 、 (S)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 、 水 、 丙酮 、 乙腈 为溶剂， 反应 260.0h， 生成 rac. Octa-O-methyl-valoneasaeure
  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：

  5-(acetoxymethyl)-3-(6-(acetoxymethyl)-2,3,4-trimethoxyphenoxy)-2-methoxyphenyl 2-iodo-3,4,5-trimethoxybenzoate 在 sodium acetate 、 palladium diacetate 、 三苯基膦 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 0.25h， 以64%的产率得到1-acetoxymethyl-3-(6-acetoxymethyl-2,3,4-trimethoxyphenoxy)-4,8,9,10-tetramethoxydibenzo[b,d]pyran-6-one
  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

文献信息

• Enantioselective synthesis of valoneic acid derivative
  作者：Hitoshi Abe、Yusuke Sahara、Yuki Matsuzaki、Yasuo Takeuchi、Takashi Harayama

  DOI：10.1016/j.tetlet.2007.11.154

  日期：2008.1

  The enantioselective synthesis of trimethyl octa-O-methylvaloneate (1) was accomplished using the Bringniann's 'lactone concept', which involves the intramolecular biaryl coupling reaction of a phenyl benzoate derivative and the asymmetric lactone-opening reaction. (c) 2007 Elsevier Ltd. All rights reserved.