methyl 9-ethyl-4,6,7-trihydroxy-5,12-dioxo-9-(triethylsilyloxy)-5,7,8,9,10,12-hexahydrotetracene-10-carboxylate | 138099-04-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 英文名称: methyl 9-ethyl-4,6,7-trihydroxy-5,12-dioxo-9-(triethylsilyloxy)-5,7,8,9,10,12-hexahydrotetracene-10-carboxylate
• CAS: 138099-04-4
• 化学式: C₂₈H₃₄O₈Si
• 分子量: 526.659
• InChiKey: YKWXHGNGOWHWDN-BUVJYCSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.74
• 重原子数：
  37.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  130.36
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  10,12-Dihydroxy-2-oxa-naphthacene-3,6,11-trione 在 Wilkinson's catalyst 氢气 、 sodium methylate 作用下， 生成 methyl 9-ethyl-4,6,7-trihydroxy-5,12-dioxo-9-(triethylsilyloxy)-5,7,8,9,10,12-hexahydrotetracene-10-carboxylate
  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

文献信息

• 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).
• 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。