(6,10,11-trimethoxy-12-oxo-3,4-dihydro-2H-tetracen-5-yl) 2,2-dimethylpropanoate | 195132-83-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (6,10,11-trimethoxy-12-oxo-3,4-dihydro-2H-tetracen-5-yl) 2,2-dimethylpropanoate
• CAS: 195132-83-3
• 化学式: C₂₆H₂₈O₆
• 分子量: 436.505
• InChiKey: LIGJQHPYTICDPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (6,10,11-trimethoxy-12-oxo-3,4-dihydro-2H-tetracen-5-yl) 2,2-dimethylpropanoate 在 4-二甲氨基吡啶 、 三氟乙酸 作用下， 以 二氯甲烷 、 氘代苯 为溶剂， 反应 12.5h， 生成 2,2-Dimethyl-propionic acid 12-acetoxy-1-ethoxy-6,10,11-trimethoxy-1,2,3,4-tetrahydro-naphthacen-5-yl 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：

  2,2-Dimethyl-propionic acid 12-hydroxy-6,10,11-trimethoxy-1,2,3,4-tetrahydro-naphthacen-5-yl ester 在 silver(l) oxide 作用下， 以 苯 为溶剂， 生成 (6,10,11-trimethoxy-12-oxo-3,4-dihydro-2H-tetracen-5-yl) 2,2-dimethylpropanoate
  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.