4-butyrylbenzoic acid tert-butyl ester | 917567-36-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-butyrylbenzoic acid tert-butyl ester
• 英文别名: tert-Butyl 4-butanoylbenzoate；tert-butyl 4-butanoylbenzoate
• CAS: 917567-36-3
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: NFQAGWVHTHQTHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 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-butyrylbenzoic acid tert-butyl ester 在 decaborane 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 16.5h， 生成 4-(1-((1-(4-(trifluoromethyl)phenyl)-1H-pyrazol-4-yl)amino)butyl)benzoic acid
  参考文献：
  名称：

  A novel series of glucagon receptor antagonists with reduced molecular weight and lipophilicity

  摘要：

  A novel series of glucagon receptor antagonists has been discovered. These pyrazole ethers and aminopyrazoles have lower molecular weight and increased polarity such that the molecules fall into better drug-like property space. This work has culminated in compounds 44 and 50 that were shown to have good pharmacokinetic attributes in dog, in contrast to rats, in which clearance was high; and compound 49, which demonstrated a dose-dependent reduction in glucose excursion in a rat glucagon challenge experiment. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.113
• 作为产物：
  描述：

  在 盐酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 以93.6 mg的产率得到4-butyrylbenzoic acid tert-butyl ester
  参考文献：
  名称：

  芳基溴化物与酰基阴离子等价物偶联钯催化合成芳基酮

  摘要：

  据报道，钯催化的芳基溴化物与作为酰基阴离子等价物的 N-叔丁基腙形成芳基酮的偶联。偶联过程发生在腙的 C 位以形成 N-叔丁基偶氮化合物。这些偶氮化合物异构化为相应的腙，然后水解，得到所需的混合烷基芳基酮。C-与N-芳基化的选择性受到氮上取代基的强烈影响。N-叔丁基腙发生碳芳基化，而N-芳基腙发生N-芳基化。含有伯和仲烷基以及芳基的腙的芳基化在水解后以良好的产率得到所需的酮。芳环上的官能团，如烷氧基、氰基、三氟甲基、碳烷氧基、氨基甲酰基和酮基，被容忍了。该反应可能通过从含有 eta1-二氮杂烯丙基配体的中间体中形成 CC 键的还原消除而发生。

  DOI：

  10.1021/ja064782t

文献信息

• A novel series of glucagon receptor antagonists with reduced molecular weight and lipophilicity
  作者：Kevin J. Filipski、Jianwei Bian、David C. Ebner、Esther C.Y. Lee、Jian-Cheng Li、Matthew F. Sammons、Stephen W. Wright、Benjamin D. Stevens、Mary T. Didiuk、Meihua Tu、Christian Perreault、Janice Brown、Karen Atkinson、Beijing Tan、Christopher T. Salatto、John Litchfield、Jeffrey A. Pfefferkorn、Angel Guzman-Perez

  DOI：10.1016/j.bmcl.2011.10.113

  日期：2012.1

  A novel series of glucagon receptor antagonists has been discovered. These pyrazole ethers and aminopyrazoles have lower molecular weight and increased polarity such that the molecules fall into better drug-like property space. This work has culminated in compounds 44 and 50 that were shown to have good pharmacokinetic attributes in dog, in contrast to rats, in which clearance was high; and compound 49, which demonstrated a dose-dependent reduction in glucose excursion in a rat glucagon challenge experiment. (C) 2011 Elsevier Ltd. All rights reserved.
• Palladium-Catalyzed Synthesis of Aryl Ketones by Coupling of Aryl Bromides with an Acyl Anion Equivalent
  作者：Akihiro Takemiya、John F. Hartwig

  DOI：10.1021/ja064782t

  日期：2006.11.1

  Palladium-catalyzed couplings of aryl bromides with N-tert-butylhydrazones as acyl anion equivalents to form aryl ketones are reported. The coupling process occurs at the C-position of hydrazones to form N-tert-butyl azo compounds. Isomerization of these azo compounds to the corresponding hydrazones, followed by hydrolysis, gave the desired mixed alkyl aryl ketones. The selectivity of C- versus N-arylation

  据报道，钯催化的芳基溴化物与作为酰基阴离子等价物的 N-叔丁基腙形成芳基酮的偶联。偶联过程发生在腙的 C 位以形成 N-叔丁基偶氮化合物。这些偶氮化合物异构化为相应的腙，然后水解，得到所需的混合烷基芳基酮。C-与N-芳基化的选择性受到氮上取代基的强烈影响。N-叔丁基腙发生碳芳基化，而N-芳基腙发生N-芳基化。含有伯和仲烷基以及芳基的腙的芳基化在水解后以良好的产率得到所需的酮。芳环上的官能团，如烷氧基、氰基、三氟甲基、碳烷氧基、氨基甲酰基和酮基，被容忍了。该反应可能通过从含有 eta1-二氮杂烯丙基配体的中间体中形成 CC 键的还原消除而发生。