4-hydroxy-9,10-dioxo-9,10-dihydroanthracen-1-yl acetate | 52869-29-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 4-hydroxy-9,10-dioxo-9,10-dihydroanthracen-1-yl acetate
• 英文别名: 1-acetoxy-4-hydroxy-anthraquinone；1-Acetoxy-4-hydroxy-anthrachinon；4-Acetoxy-1-hydroxy-anthrachinon；(4-Hydroxy-9,10-dioxo-1-anthryl) acetate；(4-hydroxy-9,10-dioxoanthracen-1-yl) acetate
• CAS: 52869-29-1
• 化学式: C₁₆H₁₀O₅
• mdl: MFCD00819441
• 分子量: 282.252
• InChiKey: WTODJCNVSBJCJT-UHFFFAOYSA-N

物化性质

• 熔点：
  186 °C(Solv: benzene (71-43-2))
• 沸点：
  509.8±50.0 °C(Predicted)
• 密度：
  1.446±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5,8-diacetoxy-1,4-naphthoquinone 在 氢氧化钾 、 氧气 作用下， 以 苯 为溶剂， 生成 4-hydroxy-9,10-dioxo-9,10-dihydroanthracen-1-yl acetate
  参考文献：
  名称：

  Takano,S. et al., Heterocycles, 1979, vol. 12, # 9, p. 1163 - 1169

  摘要：

  DOI：

文献信息

• Synthesis of New Cytotoxic Aminoanthraquinone Derivatives via Nucleophilic Substitution Reactions
  作者：Siti Nor、Mohd Sukari、Saripah Azziz、Wong Fah、Hasimah Alimon、Siti Juhan

  DOI：10.3390/molecules18078046

  日期：——

  Aminoanthraquinones were successfully synthesized via two reaction steps. 1,4-Dihydroxyanthraquinone (1) was first subjected to methylation, reduction and acylation to give an excellent yield of anthracene-1,4-dione (3), 1,4-dimethoxyanthracene-9,10-dione (5) and 9,10-dioxo-9,10-dihydroanthracene-1,4-diyl diacetate (7). Treatment of 1, 3, 5 and 7 with BuNH2 in the presence of PhI(OAc)2 as catalyst produced seven aminoanthraquinone derivatives 1a, b, 3a, and 5a–d. Amination of 3 and 5 afforded three new aminoanthraquinones, namely 2-(butylamino)anthracene-1,4-dione (3a), 2-(butylamino)anthracene-9,10-dione (5a) and 2,3-(dibutylamino)anthracene-9,10-dione (5b). All newly synthesised aminoanthraquinones were examined for their cytotoxic activity against MCF-7 (estrogen receptor positive human breast) and Hep-G2 (human hepatocellular liver carcinoma) cancer cells using MTT assay. Aminoanthraquinones 3a, 5a and 5b exhibited strong cytotoxicity towards both cancer cell lines (IC50 1.1–13.0 µg/mL).

  通过两步反应步骤，成功合成了氨基蒽醌。首先将1,4-二羟基蒽醌（1）进行甲基化、还原和酰化，得到了高产率的蒽-1,4-二酮（3）、1,4-二甲氧基蒽-9,10-二酮（5）和9,10-二氧代-9,10-二氢蒽-1,4-二基二乙酸酯（7）。将1、3、5和7与BuNH2反应，在PhI(OAc)2催化剂存在下，生成了七个氨基蒽醌衍生物1a、b、3a和5a–d。对3和5的胺化反应得到了三个新的氨基蒽醌，即2-(正丁氨基)蒽-1,4-二酮（3a）、2-(正丁氨基)蒽-9,10-二酮（5a）和2,3-(二正丁氨基)蒽-9,10-二酮（5b）。所有新合成的氨基蒽醌都通过MTT assay检测了它们对MCF-7（雌激素受体阳性人乳腺癌）和Hep-G2（人肝细胞肝癌）癌细胞的细胞毒活性。氨基蒽醌3a、5a和5b对这两种癌细胞系表现出强烈的细胞毒性（IC50为1.1–13.0 µg/mL）。
• DEGRADATION ACCELERATOR FOR POLYMERS AND POLYMER ARTICLE COMPRISING IT
  申请人：Sala Massimiliano

  公开号：US20100222454A1

  公开（公告）日：2010-09-02

  Disclosed are a method for improving the degradation of natural and/or synthetic polymers or a polymer article made from such polymer(s) by light and/or heat and/or humidity, comprising the incorporation of a compound of formula (I) into said natural and/or synthetic polymers: Formula (I); wherein m is 1 or 2, n is 1 to 100, X is selected from certain benzophenone-derived moieties and R, R1; R2 are each selected from list of certain residues; novel compounds of said formula (I) and polymeric articles of improved degradability in the presence of light and/or heat and/or humidity being made of a composition comprising: A) a natural and/or a synthetic polymer and B) a degradation accelerator being a compound of said formula (I).

  本发明涉及一种改善天然和/或合成聚合物或由这些聚合物制成的聚合物制品在光、热和/或湿度下降解的方法，包括将式(I)的化合物引入所述天然和/或合成聚合物中：式(I)；其中m为1或2，n为1至100，X选自某些苯并酮衍生物基团，R，R1和R2各自选自某些残基列表；所述式(I)的新化合物和改进的降解性能的聚合物制品由以下组成：A）天然和/或合成聚合物和B）一种降解加速剂，该加速剂是式(I)的化合物。
• Dimroth; Hilcken, Chemische Berichte, 1921, vol. 54, p. 3057
  作者：Dimroth、Hilcken

  DOI：——

  日期：——
• TAKANO S.; HATAKEYMA S.; OGASAWARA K.; KAMETANI T., HETEROCYCLES, 1979, 12, NO 9, 1163-1169,
  作者：TAKANO S.、 HATAKEYMA S.、 OGASAWARA K.、 KAMETANI T.

  DOI：——

  日期：——
• Takano,S. et al., Heterocycles, 1979, vol. 12, # 9, p. 1163 - 1169
  作者：Takano,S. et al.

  DOI：——

  日期：——