N-(3-butan-2-yl-4-hydroxyphenyl)acetamide | 13780-89-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(3-butan-2-yl-4-hydroxyphenyl)acetamide
• CAS: 13780-89-7
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: RVLBYXHBLPOQKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(3-butan-2-yl-4-hydroxyphenyl)acetamide 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 49.0h， 生成 4-Amino-2-sec-butyl-6-diethylaminomethyl-phenol; hydrochloride
  参考文献：
  名称：

  Antimalarial drugs. 61. Synthesis and antimalarial effects of 4-[(7-chloro-4-quinolinyl)amino]-2-[(diethylamino)methyl]-6-alkylphenols and their N.omega.-oxides

  摘要：

  A series of 4-[(7-chloro-4-quinolinyl)amino]-2-[(diethylamino)methyl]-6-alkylphenols and their N omega-oxides were synthesized by the condensation of 4,7-dichloroquinoline and 4,7-dichloroquinoline N omega-oxide with appropriately substituted 4-amino-2-[(diethylamino)methyl]-6-alkylphenol dihydrochlorides. The latter precursors were prepared in a six-step synthesis starting from available 2-alkylphenols. Several of the title compounds display potent antimalarial activity in mice.

  DOI：

  10.1021/jm00388a027
• 作为产物：
  描述：

  2-仲丁基苯酚 在 镍 盐酸 、 氢气 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 11.0h， 生成 N-(3-butan-2-yl-4-hydroxyphenyl)acetamide
  参考文献：
  名称：

  Antimalarial drugs. 61. Synthesis and antimalarial effects of 4-[(7-chloro-4-quinolinyl)amino]-2-[(diethylamino)methyl]-6-alkylphenols and their N.omega.-oxides

  摘要：

  A series of 4-[(7-chloro-4-quinolinyl)amino]-2-[(diethylamino)methyl]-6-alkylphenols and their N omega-oxides were synthesized by the condensation of 4,7-dichloroquinoline and 4,7-dichloroquinoline N omega-oxide with appropriately substituted 4-amino-2-[(diethylamino)methyl]-6-alkylphenol dihydrochlorides. The latter precursors were prepared in a six-step synthesis starting from available 2-alkylphenols. Several of the title compounds display potent antimalarial activity in mice.

  DOI：

  10.1021/jm00388a027

文献信息

• New 4-Aminoquinoline Mannich Base Antimalarials. 1. Effect of an Alkyl Substituent in the 5‘-Position of the 4‘-Hydroxyanilino Side Chain
  作者：Kaylene J. Raynes、Paul A. Stocks、Paul M. O'Neill、B. Kevin Park、Stephen A. Ward

  DOI：10.1021/jm9901374

  日期：1999.7.1

  have been synthesized, in which the 3'-diethylamino function of amodiaquine (AQ) is replaced by a 3'-tert-butylamino group and an aliphatic hydrocarbon entity is incorporated into the 5'-position of the 4'-hydroxyanilino side chain. Seven alkyl Mannich base derivatives were screened and found to be active against both chloroquine-sensitive and -resistant strains of Plasmodium falciparum in vitro. The propyl

  合成了一系列新的4-氨基喹啉曼尼希碱衍生物，其中氨二喹（AQ）的3'-二乙基氨基官能团被3'-叔丁基氨基取代，脂族烃实体被引入5'- 4'-羟基苯胺基侧链的位置。筛选了七个烷基曼尼希碱衍生物，发现它们在体外对氯喹敏感和耐药的恶性疟原虫菌株均具有活性。发现丙基和异丙基烷基衍生物是活性最高的。因此，对这些衍生物进行了体内抗伯氏疟原虫菌株的测试，发现其活性比AQ高3倍，而与给药途径（口服或腹膜内）无关。
• KESTEN S. J.; JOHNSON J.; WERBEL L. M., J. MED. CHEM., 30,(1987) N 5, 906-911
  作者：KESTEN S. J.、 JOHNSON J.、 WERBEL L. M.

  DOI：——

  日期：——
• Antimalarial drugs. 61. Synthesis and antimalarial effects of 4-[(7-chloro-4-quinolinyl)amino]-2-[(diethylamino)methyl]-6-alkylphenols and their N.omega.-oxides
  作者：Stephen J. Kesten、Judith Johnson、Leslie M. Werbel

  DOI：10.1021/jm00388a027

  日期：1987.5

  A series of 4-[(7-chloro-4-quinolinyl)amino]-2-[(diethylamino)methyl]-6-alkylphenols and their N omega-oxides were synthesized by the condensation of 4,7-dichloroquinoline and 4,7-dichloroquinoline N omega-oxide with appropriately substituted 4-amino-2-[(diethylamino)methyl]-6-alkylphenol dihydrochlorides. The latter precursors were prepared in a six-step synthesis starting from available 2-alkylphenols. Several of the title compounds display potent antimalarial activity in mice.