8,9,10-Trihydroxy-4-oxo-1,2,3,4-tetrahydro-3-(3-oxo-pentyl)-3-(2-oxa-1-oxo-4-pentenyl)anthracene-2-acetic Acid, Methyl Ester | 135106-34-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 8,9,10-Trihydroxy-4-oxo-1,2,3,4-tetrahydro-3-(3-oxo-pentyl)-3-(2-oxa-1-oxo-4-pentenyl)anthracene-2-acetic Acid, Methyl Ester
• 英文别名: prop-2-enyl 5,9,10-trihydroxy-3-(2-methoxy-2-oxoethyl)-1-oxo-2-(3-oxopentyl)-3,4-dihydroanthracene-2-carboxylate
• CAS: 135106-34-2
• 化学式: C₂₆H₂₈O₉
• 分子量: 484.503
• InChiKey: CESWTJZIJYJQKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  147.43
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  8,9,10-Trihydroxy-4-oxo-1,2,3,4-tetrahydro-3-(3-oxo-pentyl)-3-(2-oxa-1-oxo-4-pentenyl)anthracene-2-acetic Acid, Methyl Ester 在 palladium diacetate 、 1,2-双(二苯基膦)乙烷 作用下， 以 乙腈 为溶剂， 反应 0.67h， 以81%的产率得到4,8-Dihydroxy-9,10-dioxo-3-(3-oxopentyl)-2-anthraceneacetic Acid, Methyl Ester
  参考文献：
  名称：

  Synthesis of 1,5- and 1,8-dihydroxyanthraquinones from a common intermediate. A direct synthesis of racemic 7-deoxyaklavinone

  摘要：

  When quinone 6 was treated with diene 7 followed by oxidation, a 1,5-dihydroxyanthraquinone was obtained. When quinone 6 was subjected to a palladium-mediated aromatization, the resulting 5-hydroxy-1,4-naphthoquinone reacted with diene 7 followed by oxidation to produce a 1,8-dihydroxyanthraquinone, a key intermediate in a direct synthesis of 7-deoxyaklavinone, a known synthetic precursor of aklavinone.

  DOI：

  10.1021/jo00017a020
• 作为产物：
  描述：

  3-Allyloxycarbonylmethyl-1-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid allyl ester 在 silver(II) oxide 、 jones reagent 、 硝酸 、 苄基三甲基氢氧化铵 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 反应 19.25h， 生成 8,9,10-Trihydroxy-4-oxo-1,2,3,4-tetrahydro-3-(3-oxo-pentyl)-3-(2-oxa-1-oxo-4-pentenyl)anthracene-2-acetic Acid, Methyl Ester
  参考文献：
  名称：

  Synthesis of 1,5- and 1,8-dihydroxyanthraquinones from a common intermediate. A direct synthesis of racemic 7-deoxyaklavinone

  摘要：

  When quinone 6 was treated with diene 7 followed by oxidation, a 1,5-dihydroxyanthraquinone was obtained. When quinone 6 was subjected to a palladium-mediated aromatization, the resulting 5-hydroxy-1,4-naphthoquinone reacted with diene 7 followed by oxidation to produce a 1,8-dihydroxyanthraquinone, a key intermediate in a direct synthesis of 7-deoxyaklavinone, a known synthetic precursor of aklavinone.

  DOI：

  10.1021/jo00017a020