N-(3-iodophenyl)isobutyramide | 430464-44-1

• 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-(3-iodophenyl)isobutyramide
• 英文别名: N-(3-iodophenyl)-2-methylpropanamide
• CAS: 430464-44-1
• 化学式: C₁₀H₁₂INO
• mdl: MFCD03139044
• 分子量: 289.116
• InChiKey: PRIINUZVNPTKMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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-(3-iodophenyl)isobutyramide 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 palladium on activated charcoal 盐酸 、 氢气 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0~80.0 ℃ 、1.38 MPa 条件下， 反应 1.0h， 生成 N-(3-piperidin-4-ylphenyl)isobutyramide
  参考文献：
  名称：

  Synthesis and SAR Investigations for Novel Melanin-Concentrating Hormone 1 Receptor (MCH₁) Antagonists Part 1. The Discovery of Arylacetamides as Viable Replacements for the Dihydropyrimidinone Moiety of an HTS Hit

  摘要：

  Melanin-concentrating hormone (MCH) is involved in the regulation of feeding, water balance, energy metabolism, general arousal and attention state, memory, cognitive functions, and psychiatric disorders. Herein, two new chemical series exemplified by N-[5-(1-{3-[2,2-bis-(4-fluoro-phenyl)-acetylamino]-propyl}-piperidin-4-yl)-2,4-difluoro-phenyl]-isobutyramide (SNAP 102739, 5m) and N-[3-(l-{3-[(S)-2-(4-fluorophenyl)-propionylamino]-propyl}-piperidin-4-yl)-4-methylphenyl]-isobutyramide ((S)-6b) are reported. These compounds were designed to improve the pharmacokinetic properties of the high-throughput screening lead compound 1 (SNAP 7941). The MCH, receptor antagonists 5m and (S)-6b show reasonable pharmacokinetic profiles (rat bioavailability = 48 and 81%, respectively). Compounds 5m and (S)-6b demonstrated the inhibition of a centrally administered MCH-evoked drinking effect, and compound 5m exhibited oral in vivo efficacy in the rat social interaction model of anxiety, with a minimum effective dose = 0.3 mg/kg.

  DOI：

  10.1021/jm060381c
• 作为产物：
  描述：

  异丁酸 、 3-碘苯胺 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以98%的产率得到N-(3-iodophenyl)isobutyramide
  参考文献：
  名称：

  由分子间氢键合片构成的晶体的机械变色发光。

  摘要：

  将可以形成分子间氢键的官能团引入高度发射性的发光体中是诱导机械致变色发光的一种有前途的方法。在此，我们报道了具有两个酰胺基的9,10-双（苯基乙炔基）蒽衍生物形成了基于二维氢键分子片的绿色发射晶体。由于从晶相到非晶相的过渡，机械研磨将发射光从绿色变为黄色。红外光谱显示，机械刺激破坏了线性氢键的形成。热处理恢复了原始的绿色光致发光。

  DOI：

  10.1002/asia.201901679

文献信息

• Synthesis and SAR Investigations for Novel Melanin-Concentrating Hormone 1 Receptor (MCH₁) Antagonists Part 1. The Discovery of Arylacetamides as Viable Replacements for the Dihydropyrimidinone Moiety of an HTS Hit
  作者：Yu Jiang、Chien-An Chen、Kai Lu、Irena Daniewska、John De Leon、Ron Kong、Carlos Forray、Boshan Li、Laxminarayan G. Hegde、Toni D. Wolinsky、Douglas A. Craig、John M. Wetzel、Kim Andersen、Mohammad R. Marzabadi

  DOI：10.1021/jm060381c

  日期：2007.8.1

  Melanin-concentrating hormone (MCH) is involved in the regulation of feeding, water balance, energy metabolism, general arousal and attention state, memory, cognitive functions, and psychiatric disorders. Herein, two new chemical series exemplified by N-[5-(1-3-[2,2-bis-(4-fluoro-phenyl)-acetylamino]-propyl}-piperidin-4-yl)-2,4-difluoro-phenyl]-isobutyramide (SNAP 102739, 5m) and N-[3-(l-3-[(S)-2-(4-fluorophenyl)-propionylamino]-propyl}-piperidin-4-yl)-4-methylphenyl]-isobutyramide ((S)-6b) are reported. These compounds were designed to improve the pharmacokinetic properties of the high-throughput screening lead compound 1 (SNAP 7941). The MCH, receptor antagonists 5m and (S)-6b show reasonable pharmacokinetic profiles (rat bioavailability = 48 and 81%, respectively). Compounds 5m and (S)-6b demonstrated the inhibition of a centrally administered MCH-evoked drinking effect, and compound 5m exhibited oral in vivo efficacy in the rat social interaction model of anxiety, with a minimum effective dose = 0.3 mg/kg.
• Mechanochromic Luminescence from Crystals Consisting of Intermolecular Hydrogen‐Bonded Sheets
  作者：Yoshimitsu Sagara、Kiyonori Takahashi、Takayoshi Nakamura、Nobuyuki Tamaoki

  DOI：10.1002/asia.201901679

  日期：2020.2.17

  10-bis(phenylethynyl)anthracene derivative featuring two amide groups forms green-emissive crystals based on two-dimensional hydrogen-bonded molecular sheets. Mechanical grinding changed the emission from green to yellow, owing to a transition from a crystalline to an amorphous phase. Infrared spectroscopy revealed that mechanical stimuli disrupted the linear hydrogen-bonding formation. A thermal treatment recovered

  将可以形成分子间氢键的官能团引入高度发射性的发光体中是诱导机械致变色发光的一种有前途的方法。在此，我们报道了具有两个酰胺基的9,10-双（苯基乙炔基）蒽衍生物形成了基于二维氢键分子片的绿色发射晶体。由于从晶相到非晶相的过渡，机械研磨将发射光从绿色变为黄色。红外光谱显示，机械刺激破坏了线性氢键的形成。热处理恢复了原始的绿色光致发光。