(4-cyclohexyl-butyric acid )-acetic acid-anhydride | 872288-30-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4-cyclohexyl-butyric acid )-acetic acid-anhydride
• 英文别名: (4-Cyclohexyl-buttersaeure)-essigsaeure-anhydrid；Acetyl 4-cyclohexylbutanoate；acetyl 4-cyclohexylbutanoate
• CAS: 872288-30-7
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: DKQVIVNDUPMVJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-cyclohexyl-butyric acid )-acetic acid-anhydride 、 4-氨基苯甲酸甲酯 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 4-(4-Cyclohexylbutanoylamino)benzoic acid
  参考文献：
  名称：

  4-[4-[(2-Hydroxybenzoyl)amino]phenyl]butyric Acid as a Novel Oral Delivery Agent for Recombinant Human Growth Hormone

  摘要：

  A series of N-acetylated, non-alpha, aromatic amino acids was prepared and shown to promote the absorption of recombinant human growth hormone (rhGH) from the gastrointestinal tract. Seventy compounds in this family were tested in vivo in rats. Of the compounds tested, 4-[4-[(2-hydroxybenzoyl)amino]phenyl]butyric acid was identified as a preclinical candidate and was used to demonstrate the oral delivery of rhGH in primates. A significant positive correlation was found between the relative log k' of the delivery agents, as determined by HPLC on an immobilized artificial membrane (IAM) column, and serum rhGH concentrations following oral or colonic dosing in rats. Structure-activity relationships have also been developed on the basis of electronic effects and hydrogen-bonding characteristics of the aromatic amide substituents.

  DOI：

  10.1021/jm960038f
• 作为产物：
  描述：

  乙烯酮 、 alkaline earth salt of/the/ methylsulfuric acid 生成 (4-cyclohexyl-butyric acid )-acetic acid-anhydride
  参考文献：
  名称：

  Acetylation of Monocarboxylic Acids with Ketene

  摘要：

  DOI：

  10.1021/ja01620a060

文献信息

• US4542142A
  申请人：——

  公开号：US4542142A

  公开（公告）日：1985-09-17
• US4883806A
  申请人：——

  公开号：US4883806A

  公开（公告）日：1989-11-28
• 4-[4-[(2-Hydroxybenzoyl)amino]phenyl]butyric Acid as a Novel Oral Delivery Agent for Recombinant Human Growth Hormone
  作者：Andrea Leone-Bay、Koc-Kan Ho、Rajesh Agarwal、Robert A. Baughman、Kiran Chaudhary、Frenel DeMorin、Lise Genoble、Campbell McInnes、Christine Lercara、Sam Milstein、Doris O'Toole、Donald Sarubbi、Bruce Variano、Duncan R. Paton

  DOI：10.1021/jm960038f

  日期：1996.1.1

  A series of N-acetylated, non-alpha, aromatic amino acids was prepared and shown to promote the absorption of recombinant human growth hormone (rhGH) from the gastrointestinal tract. Seventy compounds in this family were tested in vivo in rats. Of the compounds tested, 4-[4-[(2-hydroxybenzoyl)amino]phenyl]butyric acid was identified as a preclinical candidate and was used to demonstrate the oral delivery of rhGH in primates. A significant positive correlation was found between the relative log k' of the delivery agents, as determined by HPLC on an immobilized artificial membrane (IAM) column, and serum rhGH concentrations following oral or colonic dosing in rats. Structure-activity relationships have also been developed on the basis of electronic effects and hydrogen-bonding characteristics of the aromatic amide substituents.
• Acetylation of Monocarboxylic Acids with Ketene
  作者：R. E. Dunbar、Floyd C. Garven

  DOI：10.1021/ja01620a060

  日期：1955.8