N-(4-Hydroxy-3-isopropyl-phenyl)-acetamide | 13780-91-1

• 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-(4-Hydroxy-3-isopropyl-phenyl)-acetamide
• 英文别名: 3-Isopropyl-4-hydroxyacetanilide；N-(4-hydroxy-3-propan-2-ylphenyl)acetamide
• CAS: 13780-91-1
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: GYWQSMVROLKSKW-UHFFFAOYSA-N

物化性质

• 熔点：
  119-120 °C
• 沸点：
  373.5±35.0 °C(Predicted)
• 密度：
  1.129±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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-(4-Hydroxy-3-isopropyl-phenyl)-acetamide 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 49.0h， 生成 4-amino-2-<(diethylamino)methyl>-6-(1-methylethyl)phenol dihydrochloride
  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：

  2,5-Cyclohexadiene-1,4-dione,2-(1-methylethyl)-,4-oxime(9CI) 在 镍 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.0h， 生成 N-(4-Hydroxy-3-isopropyl-phenyl)-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

• Macrolactams by engineered biosynthesis
  申请人：Ashley Gary W.

  公开号：US20080188450A1

  公开（公告）日：2008-08-07

  Macrolactams are made by feeding aromatic amino acids as replacement starter units to a mutant strain of the geldanamycin-producing microorganism Streptomyces hygroscopicus var. geldanus NRRL 3602, wherein the gene cluster encoding enzymes for the biosynthesis of the natural starter unit 3-amino-5-hydroxybenzoic acid has been deleted.

  大环内酰胺是通过将芳香族氨基酸作为替代起始单元供应给生产格尔达霉素的微生物链霉菌属湿生链霉菌格尔达努斯NRRL 3602的突变菌株制备的，其中编码天然起始单元3-氨基-5-羟基苯甲酸生物合成酶的基因簇已被删除。
• 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：——
• US7855192B2
  申请人：——

  公开号：US7855192B2

  公开（公告）日：2010-12-21
• 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.