1-(丁基氨基)-4-羟基蒽醌 | 63768-01-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 1-(丁基氨基)-4-羟基蒽醌
• 英文名称: 1-(butylamino)-4-hydroxyanthracene-9,10-dione
• 英文别名: 1-hydroxy-4-butylaminoantraquinone；1-butylamino-4-hydroxy-9,10 anthracene dione；1-(Butylamino)-4-hydroxyanthraquinone
• CAS: 63768-01-4
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: MLZFWBQTQKBDSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2922509090

反应信息

• 作为产物：
  描述：

  1,4-二羟基蒽醌 、 正丁胺 生成 1-(丁基氨基)-4-羟基蒽醌
  参考文献：
  名称：

  MATSUOKA MASARU; MAKINO YOSHINOBU; YOSHIDA KATSUHIRA; KITAO TEIJIHIRO, CHEM. LETT., 1979, NO 11, 1347-1348

  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）。
• The Direct Alkylamination of α-Substituted Anthraquinones Promoted by Metal Ions
  作者：Masaru Matsuoka、Toshio Takei、Isao Nakamura、Katsuhira Yoshida、Teijiro Kitao

  DOI：10.1246/bcsj.54.2225

  日期：1981.7

  The reaction of 1-amino-4-acylaminoanthraquinones with piperidine in the presence of CoCl2 and atmospheric oxygen gave the 2-aminated products in 75–80%, and similar reaction of 1-hydroxyanthraquinone or 1-aminoanthraquinone-2-sulfonic acid with butylamine gave the corresponding 4-aminated products, respectively. The effects of the α-substituents and the role of metal salts were discussed.

  1-amino-4-acylaminoanthraquinones 与哌啶在 CoCl2 和大气氧存在下发生反应，得到 75-80% 的 2-氨基产物；1-hydroxyanthraquinone 或 1-aminoanthraquinone-2-sulfonic acid 与丁胺发生类似反应，分别得到相应的 4-氨基产物。讨论了 α 取代基的影响和金属盐的作用。
• Markers for petroleum, method of tagging, and method of detection
  申请人：MORTON INTERNATIONAL, INC.

  公开号：EP0609591B1

  公开（公告）日：1997-07-23
• MATSUOKA MASARU; YOSHIDA KATSUHIRA; MAKINO YOSHINOBU; KITAO TEIJIRO, DYES AND PIGM., 1980, 1, NO 1, 27-37
  作者：MATSUOKA MASARU、 YOSHIDA KATSUHIRA、 MAKINO YOSHINOBU、 KITAO TEIJIRO

  DOI：——

  日期：——
• MATSUOKA, MASARU;TAKEI, TOSHIO;NAKAMURA, ISAO;YOSHIDA, KATSUHIRA;KITAO, T+, BULL. CHEM. SOC. JAP., 1981, 54, N 7, 2225-2226
  作者：MATSUOKA, MASARU、TAKEI, TOSHIO、NAKAMURA, ISAO、YOSHIDA, KATSUHIRA、KITAO, T+

  DOI：——

  日期：——