5,12-Bis-(2,2-dimethyl-propionyloxy)-6,7,11-trimethoxy-4-oxo-1,2,3,4-tetrahydro-naphthacene-2-carboxylic acid methyl ester | 195132-93-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 5,12-Bis-(2,2-dimethyl-propionyloxy)-6,7,11-trimethoxy-4-oxo-1,2,3,4-tetrahydro-naphthacene-2-carboxylic acid methyl ester
• 英文别名: methyl 5,12-bis(2,2-dimethylpropanoyloxy)-6,7,11-trimethoxy-4-oxo-2,3-dihydro-1H-tetracene-2-carboxylate
• CAS: 195132-93-5
• 化学式: C₃₃H₃₈O₁₀
• 分子量: 594.659
• InChiKey: WATCWWFHAZCSAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  43
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5,12-Bis-(2,2-dimethyl-propionyloxy)-6,7,11-trimethoxy-4-oxo-1,2,3,4-tetrahydro-naphthacene-2-carboxylic acid methyl ester 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 以74%的产率得到12-(2,2-Dimethyl-propionyloxy)-5-hydroxy-6,7,11-trimethoxy-1,2,3,4-tetrahydro-naphthacene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and Chemistry of Quinone Methide Models for the Anthracycline Antitumor Antibiotics

  摘要：

  In an effort to further understand the chemistry of anthracycline-type quinone methides, two tetracyclic o-quinone methides, 4,5,12-trimethoxy-11-[(trimethylacetyl)oxy]-3-9,10-dihydro-6(2H)-naphthacenone (19) and (+/-)-9-carbomethoxy-4,5,12-trimethoxy-11-[(trimethylacetyl)oxy]-9,10-di-hydro-6(2H)-naphthacenone (20), were synthesized, and their reaction with several nucleophiles was investigated. Carbon-and sulfur-based nucleophiles afforded stable adducts while oxygen-and nitrogen-based nucleophiles afforded unstable adducts due to the reversibility of the addition. Adducts of 19 with ethanol and O-silylated adenosine (27) were acetylated to afford stable phenol acetates 21 and 29, respectively.

  DOI：

  10.1021/jo970539o
• 作为产物：
  描述：

  3-Benzenesulfonyl-4,8,9-trimethoxy-3H-naphtho[2,3-c]furan-1-one 在 4-二甲氨基吡啶 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 5.08h， 生成 5,12-Bis-(2,2-dimethyl-propionyloxy)-6,7,11-trimethoxy-4-oxo-1,2,3,4-tetrahydro-naphthacene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and Chemistry of Quinone Methide Models for the Anthracycline Antitumor Antibiotics

  摘要：

  In an effort to further understand the chemistry of anthracycline-type quinone methides, two tetracyclic o-quinone methides, 4,5,12-trimethoxy-11-[(trimethylacetyl)oxy]-3-9,10-dihydro-6(2H)-naphthacenone (19) and (+/-)-9-carbomethoxy-4,5,12-trimethoxy-11-[(trimethylacetyl)oxy]-9,10-di-hydro-6(2H)-naphthacenone (20), were synthesized, and their reaction with several nucleophiles was investigated. Carbon-and sulfur-based nucleophiles afforded stable adducts while oxygen-and nitrogen-based nucleophiles afforded unstable adducts due to the reversibility of the addition. Adducts of 19 with ethanol and O-silylated adenosine (27) were acetylated to afford stable phenol acetates 21 and 29, respectively.

  DOI：

  10.1021/jo970539o

文献信息

• Synthesis and Chemistry of Quinone Methide Models for the Anthracycline Antitumor Antibiotics
  作者：Steven R. Angle、Jon D. Rainier、Catherine Woytowicz

  DOI：10.1021/jo970539o

  日期：1997.8.1

  In an effort to further understand the chemistry of anthracycline-type quinone methides, two tetracyclic o-quinone methides, 4,5,12-trimethoxy-11-[(trimethylacetyl)oxy]-3-9,10-dihydro-6(2H)-naphthacenone (19) and (+/-)-9-carbomethoxy-4,5,12-trimethoxy-11-[(trimethylacetyl)oxy]-9,10-di-hydro-6(2H)-naphthacenone (20), were synthesized, and their reaction with several nucleophiles was investigated. Carbon-and sulfur-based nucleophiles afforded stable adducts while oxygen-and nitrogen-based nucleophiles afforded unstable adducts due to the reversibility of the addition. Adducts of 19 with ethanol and O-silylated adenosine (27) were acetylated to afford stable phenol acetates 21 and 29, respectively.