3-formyl-4,5-dihydroxy-9,10-dioxo-2-anthrylacetic acid | 138098-95-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 3-formyl-4,5-dihydroxy-9,10-dioxo-2-anthrylacetic acid
• CAS: 138098-95-0
• 化学式: C₁₇H₁₀O₇
• 分子量: 326.262
• InChiKey: TZHABBMHWIFYEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.31
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  128.97
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-formyl-4,5-dihydroxy-9,10-dioxo-2-anthrylacetic acid 在 Wilkinson's catalyst 氢气 、 sodium methylate 、 乙酸酐 、 2,5-降冰片二烯 作用下， 以 苯 为溶剂， 生成 (1R,2R,4R)-2-Ethyl-5,7-dihydroxy-4-methoxy-6,11-dioxo-2-triethylsilanyloxy-1,2,3,4,6,11-hexahydro-naphthacene-1-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of anthracyclinones via o-quinonoid pyrones

  摘要：

  酸3(R = H)与乙酸酐在80℃下脱水生成邻醌型吡喃酮4，它可以被多种烯烃捕获；加合物 6(R = Me, P = SiEt3) 及其来自 2-三乙基甲硅烷氧基丙烯的 9-差向异构体很容易转化为 (±)-金霉素酮，而那些 [(6; R = 乙烯基, P = SiEt3) 及其 9-差向异构体]由2-三乙基甲硅烷氧基丁-1,3-二烯生成的产物很容易转化为甲基醚12、13、14和15，其中已知12、14和15很容易转化为(±)-aklavinone。

  DOI：

  10.1039/c39910001509
• 作为产物：
  描述：

  (3-Formyl-4,5-dihydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-yl)-acetic acid methyl ester 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以66%的产率得到3-formyl-4,5-dihydroxy-9,10-dioxo-2-anthrylacetic acid
  参考文献：
  名称：

  Synthesis of (±)-aklavinone and (±)-auramycinone via electron-deficient o-quinonoid pyrones

  摘要：

  Dehydration of the formyl acid 3 (R = H) with acetic anhydride in benzene at 80 degrees C generates the quinonoid pyrone 4 which can be trapped with norbornadiene, N-phenylmaleimide and enol silyl ethers; the adduct 6 (R = Me, P = TES) and its 9-epimer 10 from 2-(triethylsilyloxy)propene are readily transformed into (+/-)-auramycinone 2 (R = Me) whilst those [6 (R =vinyl, P = TES) and its 9-epimer] from 2(triethylsilyloxy)buta- 1,3-diene are readily converted into the methyl ethers 24, 25, 33 and 34 of which 24, 33 and 34 are known to be readily converted into (+/-)-aklavinone 2 (R = Et).

  DOI：

  10.1039/p19950002747

文献信息

• Synthesis of anthracyclinones via o-quinonoid pyrones
  作者：David W. Jones、Christopher J. Lock

  DOI：10.1039/c39910001509

  日期：——

  Dehydration of the acid 3(R = H) with acetic anhydride at 80 °C generates the o-quinonoid pyrone 4 which can be trapped with several alkenes; the adduct 6(R = Me, P = SiEt3) and its 9-epimer from 2-triethylsilyloxypropene are readily transformed into (±)-auramycinone whilst those [(6; R = vinyl, P = SiEt3) and its 9-epimer] from 2-triethylsilyloxybuta-1,3-diene are readily converted into the methyl ethers 12, 13, 14 and 15 of which 12, 14 and 15 are known to be readily converted into (±)-aklavinone.

  酸3(R = H)与乙酸酐在80℃下脱水生成邻醌型吡喃酮4，它可以被多种烯烃捕获；加合物 6(R = Me, P = SiEt3) 及其来自 2-三乙基甲硅烷氧基丙烯的 9-差向异构体很容易转化为 (±)-金霉素酮，而那些 [(6; R = 乙烯基, P = SiEt3) 及其 9-差向异构体]由2-三乙基甲硅烷氧基丁-1,3-二烯生成的产物很容易转化为甲基醚12、13、14和15，其中已知12、14和15很容易转化为(±)-aklavinone。
• Synthesis of (±)-aklavinone and (±)-auramycinone via electron-deficient o-quinonoid pyrones
  作者：David W. Jones、Christopher J. Lock

  DOI：10.1039/p19950002747

  日期：——

  Dehydration of the formyl acid 3 (R = H) with acetic anhydride in benzene at 80 degrees C generates the quinonoid pyrone 4 which can be trapped with norbornadiene, N-phenylmaleimide and enol silyl ethers; the adduct 6 (R = Me, P = TES) and its 9-epimer 10 from 2-(triethylsilyloxy)propene are readily transformed into (+/-)-auramycinone 2 (R = Me) whilst those [6 (R =vinyl, P = TES) and its 9-epimer] from 2(triethylsilyloxy)buta- 1,3-diene are readily converted into the methyl ethers 24, 25, 33 and 34 of which 24, 33 and 34 are known to be readily converted into (+/-)-aklavinone 2 (R = Et).