N-(4-butylphenyl)pivalamide | 133461-99-1

• 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-butylphenyl)pivalamide
• 英文别名: N-(4-Butyl-phenyl)-2,2-dimethyl-propionamide；N-(4-butylphenyl)-2,2-dimethylpropanamide
• CAS: 133461-99-1
• 化学式: C₁₅H₂₃NO
• mdl: MFCD01034348
• 分子量: 233.354
• InChiKey: ZPASUSFSPSBZOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.533
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(4-butylphenyl)pivalamide 在 盐酸 、 sodium hydroxide 、 sodium tetrahydroborate 、 正丁基锂 、 四甲基乙二胺 作用下， 以 1,4-二氧六环 、 乙醚 、 乙醇 、 正己烷 为溶剂， 反应 9.0h， 生成 4-Butyl-2-chloromethyl-phenylamine; hydrochloride
  参考文献：
  名称：

  Substituted 2-[(2-benzimidazolylsulfinyl)methyl]anilines as potential inhibitors of H+/K+ ATPase

  摘要：

  A series of substituted 2-[(2-benzimidazolylsulfinyl)methyl]anilines were synthesized as potential inhibitors of the acid secretory enzyme H+/K+ ATPase. Substitutions on the aniline nitrogen atom resulted in potent enzyme inhibition in vitro but weak activity in gastric fistula dogs. Electron-donating substituents on the aniline ring enhanced in vitro and in vivo potency relative to the unsubstituted analogue. The potency showed a correlation to the calculated pKa of the aniline nitrogen atom. Substitutions on the aniline and benzimidazole rings did not further enhance potency. Di- and trisubstituted aniline derivatives were potent inhibitors of the enzyme system. The preferred combination of substituents were a methoxy group on the benzimidazole ring and a single alkyl group on the aniline ring. One such compound, 76, was an effective inhibitor of acid secretion in the dog and was selected for further pharmacological study.

  DOI：

  10.1021/jm00401a024
• 作为产物：
  描述：

  4-正丁基苯胺 、 三甲基乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-(4-butylphenyl)pivalamide
  参考文献：
  名称：

  Substituted 2-[(2-benzimidazolylsulfinyl)methyl]anilines as potential inhibitors of H+/K+ ATPase

  摘要：

  A series of substituted 2-[(2-benzimidazolylsulfinyl)methyl]anilines were synthesized as potential inhibitors of the acid secretory enzyme H+/K+ ATPase. Substitutions on the aniline nitrogen atom resulted in potent enzyme inhibition in vitro but weak activity in gastric fistula dogs. Electron-donating substituents on the aniline ring enhanced in vitro and in vivo potency relative to the unsubstituted analogue. The potency showed a correlation to the calculated pKa of the aniline nitrogen atom. Substitutions on the aniline and benzimidazole rings did not further enhance potency. Di- and trisubstituted aniline derivatives were potent inhibitors of the enzyme system. The preferred combination of substituents were a methoxy group on the benzimidazole ring and a single alkyl group on the aniline ring. One such compound, 76, was an effective inhibitor of acid secretion in the dog and was selected for further pharmacological study.

  DOI：

  10.1021/jm00401a024

文献信息

• SUBSTITUTED HYDROXAMIC ACIDS AND USES THEREOF
  申请人：Blackburn Christopher

  公开号：US20110213003A1

  公开（公告）日：2011-09-01

  This invention provides compounds of formula (I): wherein X 1 , X 2 , X 3 , R 2 , R 4b , R 1 , and G have values as described in the specification, useful as inhibitors of HDAC6. The invention also provides pharmaceutical compositions comprising the compounds of the invention and methods of using the compositions in the treatment of proliferative, inflammatory, infectious, neurological or cardiovascular diseases or disorders.

  这项发明提供了式（I）的化合物： 其中X 1 ，X 2 ，X 3 ，R 2 ，R 4b ，R 1 和G的取值如规范中所述，可用作HDAC6的抑制剂。该发明还提供了包括该发明化合物的药物组合物，以及在治疗增殖性、炎症性、感染性、神经系统或心血管疾病或紊乱中使用这些组合物的方法。
• Rhodium-Catalyzed Oxidative Benzannulation of<i>N</i>-Pivaloylanilines with Internal Alkynes through Dual C−H Bond Activation: Synthesis of Highly Substituted Naphthalenes
  作者：Xuan Zhang、Xiaoqiang Yu、Xiujuan Feng、Yoshinori Yamamoto、Abdulrahman I. Almansour、Natarajan Arumugam、Raju Suresh Kumar、Ming Bao

  DOI：10.1002/asia.201601131

  日期：2016.11.22

  An efficient method was developed for the synthesis of highly substituted naphthalenes through rhodium‐catalyzed oxidative benzannulation of N‐pivaloylanilines with internal alkynes. The benzannulation reaction proceeded smoothly through dual C−H bond activation to produce the corresponding highly substituted naphthalene products in satisfactory to good yields.

  通过铑催化的N-新戊酰苯胺与内部炔烃的氧化苯甲酸酯合成，开发了一种高效的方法来合成高度取代的萘。苯环化反应通过双C-H键活化反应顺利进行，以令人满意的产率获得了相应的高度取代的萘产品。
• Regioselective <i>ortho</i> halogenation of <i>N</i>-aryl amides and ureas <i>via</i> oxidative halodeboronation: harnessing boron reactivity for efficient C–halogen bond installation
  作者：Ganesh H. Shinde、Ganesh S. Ghotekar、Francoise M. Amombo Noa、Lars Öhrström、Per-Ola Norrby、Henrik Sundén

  DOI：10.1039/d3sc04628a

  日期：——

  ortho position of N-aryl amides and ureas represents a tool to prepare motifs that are ubiquitous in biologically active compounds. To construct such prevalent bonds, most methods require the use of precious metals and a multistep process. Here we report a novel protocol for the long-standing challenge of regioselective ortho halogenation of N-aryl amides and ureas using an oxidative halodeboronation

  在N-芳基酰胺和脲的邻位安装 C-卤素键代表了一种制备生物活性化合物中普遍存在的基序的工具。为了构建这种普遍的债券，大多数方法都需要使用贵金属和多步骤过程。在这里，我们报告了一种新的方案，用于解决使用氧化卤代硼化对N-芳基酰胺和脲进行区域选择性邻位卤化的长期挑战。通过利用硼对氮的反应性，我们将羰基定向硼化与连续卤代硼化结合起来，从而能够在N-芳基酰胺和脲所需的邻位精确引入 C-X 键。该方法为在温和条件下合成卤化N-杂芳烃提供了一种高效、实用且可扩展的解决方案，突出了硼反应性在指导反应区域选择性方面的优越性。
• Substituted 2-[(2-benzimidazolylsulfinyl)methyl]anilines as potential inhibitors of H+/K+ ATPase
  作者：Gilbert W. Adelstein、Chung H. Yen、Richard A. Haack、Stella Yu、Gary Gullikson、Doreen V. Price、Charles Anglin、Dennis L. Decktor、Henry Tsai、Robert H. Keith

  DOI：10.1021/jm00401a024

  日期：1988.6

  A series of substituted 2-[(2-benzimidazolylsulfinyl)methyl]anilines were synthesized as potential inhibitors of the acid secretory enzyme H+/K+ ATPase. Substitutions on the aniline nitrogen atom resulted in potent enzyme inhibition in vitro but weak activity in gastric fistula dogs. Electron-donating substituents on the aniline ring enhanced in vitro and in vivo potency relative to the unsubstituted analogue. The potency showed a correlation to the calculated pKa of the aniline nitrogen atom. Substitutions on the aniline and benzimidazole rings did not further enhance potency. Di- and trisubstituted aniline derivatives were potent inhibitors of the enzyme system. The preferred combination of substituents were a methoxy group on the benzimidazole ring and a single alkyl group on the aniline ring. One such compound, 76, was an effective inhibitor of acid secretion in the dog and was selected for further pharmacological study.