4-Hydroxy-5,8-dihydro-5,8-dioxo-3-(3-oxopentyl)-naphthaleneactic Acid, Methyl Ester | 135106-36-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-Hydroxy-5,8-dihydro-5,8-dioxo-3-(3-oxopentyl)-naphthaleneactic Acid, Methyl Ester
• 英文别名: methyl 2-[4-hydroxy-5,8-dioxo-3-(3-oxopentyl)naphthalen-2-yl]acetate
• CAS: 135106-36-4
• 化学式: C₁₈H₁₈O₆
• 分子量: 330.337
• InChiKey: CAHNPTFRMVDDEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.95
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  97.74
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-Hydroxy-5,8-dihydro-5,8-dioxo-3-(3-oxopentyl)-naphthaleneactic Acid, Methyl Ester 在 吡啶 、 jones reagent 、 苄基三甲基氢氧化铵 作用下， 以 甲醇 为溶剂， 反应 32.0h， 生成 methyl 9(R,S)-ethyl-4,6,9(R,S)-trihydroxy-5,12-dioxo-7,8,9,10-tetrahydronaphthacene-10(R,S)-carboxylate
  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-Methoxycarbonylmethyl-1,5,8-trioxo-2-(3-oxo-pentyl)-1,2,3,4,5,8-hexahydro-naphthalene-2-carboxylic acid allyl ester 在 palladium diacetate 、 1,2-双(二苯基膦)乙烷 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 生成 4-Hydroxy-5,8-dihydro-5,8-dioxo-3-(3-oxopentyl)-naphthaleneactic 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

文献信息

• KRAUS, GEORGE A.;CHEN, LI, J. ORG. CHEM., 56,(1991) N7, C. 5098-5100
  作者：KRAUS, GEORGE A.、CHEN, LI

  DOI：——

  日期：——