N-(2-methoxybenzyl)butyramide | 111088-39-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(2-methoxybenzyl)butyramide
• 英文别名: N-(2-methoxybenzyl)butanamide；N-[(2-methoxyphenyl)methyl]butanamide
• CAS: 111088-39-2
• 化学式: C₁₂H₁₇NO₂
• mdl: MFCD00752496
• 分子量: 207.272
• InChiKey: HIXFASOHBYDACU-UHFFFAOYSA-N

物化性质

• 沸点：
  145-148 °C(Press: 0.3 Torr)
• 密度：
  1.027±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-methoxybenzyl)butyramide 在 sodium hydroxide 、 三(三氟乙酸)碘 、 三溴化硼 、 铜 、 三乙胺 、 sodium bromide 作用下， 以 甲醇 为溶剂， 生成 (S)-2-Amino-3-{4-[3-(butyrylamino-methyl)-4-hydroxy-phenoxy]-3,5-diiodo-phenyl}-propionic acid
  参考文献：
  名称：

  Thyroid hormone analogs. Synthesis of 3'-substituted 3,5-diiodo-L-thyronines and quantitative structure-activity studies of in vitro and in vivo thyromimetic activities in rat liver and heart

  摘要：

  Twenty-nine novel 3'-substituted derivatives of the thyroid hormone 3,3',5-triiodo-L-thyronine (T3) have been synthesized by using established methods and by a new route involving manipulation of a 3'-formyl intermediate. In vitro hormone receptor binding (to intact nuclei) and in vivo thyromimetic activity (induction of mitochondrial 3-phosphoglycerate oxidoreductase, GPDH) were measured in rat liver and heart for these new analogues and for the 18 previously reported 3'-substituted 3,5-diiodo-L-thyronines. Analysis of the binding data using theoretical conformational and quantitative structure-affinity methods implies that the 3'-substituent recognition site on the thyroid hormone receptor is hydrophobic and limited in depth to the length of the natural iodo substituent, but has sufficient width to accommodate a phenyl or cyclohexyl group. Receptor binding is reduced by approximately 10-fold in 3'-acyl derivatives which form strong intramolecular acceptor hydrogen bonds with the adjacent 4'-hydroxyl. The compounds studied showed no differences in their relative affinities for heart and liver nuclei, suggesting that receptors in these tissues are similar. However, the relationships between thyromimetic activity (induction of GPDH) and nuclear binding showed some tissue differences. A high correlation between activity and binding is observed for full agonists in the heart, but an equally significant correlation for the liver data is only seen when 3'-substituent bulk (molar refractivity) is included in the analysis. These results suggest the possibility that differential tissue penetration or access to receptors may occur in vivo.

  DOI：

  10.1021/jm00396a008
• 作为产物：
  描述：

  丁酰胺 、 邻甲氧基苯甲醛 在 一氧化碳 、 C₁₄H₁₀*Ru⁽²⁺⁾*C₁₁H₁₇O^(1-)*F₆P^(1-) 作用下， 以 乙醚 为溶剂， 160.0 ℃ 、3.04 MPa 条件下， 反应 22.0h， 以73%的产率得到N-(2-methoxybenzyl)butyramide
  参考文献：
  名称：

  没有外部氢源的钌催化还原酰胺化

  摘要：

  开发了原子经济的Ru催化的醛还原酰胺化反应的催化体系。在此过程中使用了环戊二烯基钌催化剂，其负载量低至0.5-1 mol％，一氧化碳用作脱氧剂。许多酰胺和芳香醛能够成功获得相应的仲酰胺，收率为79–84％。

  DOI：

  10.1002/ejoc.201701527

文献信息

• LEESON, PAUL D.;ELLIS, DAVID;EMMETT, JOHN C.;SHAH, VIRENDRA P.;SHOWELL, G+, J. MED. CHEM., 31,(1988) N 1, 37-54
  作者：LEESON, PAUL D.、ELLIS, DAVID、EMMETT, JOHN C.、SHAH, VIRENDRA P.、SHOWELL, G+

  DOI：——

  日期：——
• [EN] PYRIDAZINONES FOR THE TREATMENT OF CANCER<br/>[FR] PYRIDAZINONES POUR LE TRAITEMENT DU CANCER
  申请人：MAX PLANCK GES ZUR FÖRDERUNG DER WISSENSCHAFTEN E V

  公开号：WO2015189433A1

  公开（公告）日：2015-12-17

  The present invention relates to novel substituted pyrrolo- and pyrazolo-pyridazinones, as well as pharmaceutical compositions containing at least one of these substituted pyrrolo- and pyrazolo-pyridazinones together with at least one pharmaceutically acceptable carrier, excipient and/or diluent. Said novel substituted pyrrolo- and pyrazolo-pyridazinones are binding to the prenyl binding pocket of PDE5 and therefore, are useful for the prophylaxis and treatment of cancer by inhibition of the binding of PDEδ to farnesylated Ras proteins and thereby, inhibition of oncogenic Ras signaling in cells.
• Thyroid hormone analogs. Synthesis of 3'-substituted 3,5-diiodo-L-thyronines and quantitative structure-activity studies of in vitro and in vivo thyromimetic activities in rat liver and heart
  作者：Paul D. Leeson、David Ellis、John C. Emmett、Virendra P. Shah、Graham A. Showell、Anthony H. Underwood

  DOI：10.1021/jm00396a008

  日期：1988.1

  Twenty-nine novel 3'-substituted derivatives of the thyroid hormone 3,3',5-triiodo-L-thyronine (T3) have been synthesized by using established methods and by a new route involving manipulation of a 3'-formyl intermediate. In vitro hormone receptor binding (to intact nuclei) and in vivo thyromimetic activity (induction of mitochondrial 3-phosphoglycerate oxidoreductase, GPDH) were measured in rat liver and heart for these new analogues and for the 18 previously reported 3'-substituted 3,5-diiodo-L-thyronines. Analysis of the binding data using theoretical conformational and quantitative structure-affinity methods implies that the 3'-substituent recognition site on the thyroid hormone receptor is hydrophobic and limited in depth to the length of the natural iodo substituent, but has sufficient width to accommodate a phenyl or cyclohexyl group. Receptor binding is reduced by approximately 10-fold in 3'-acyl derivatives which form strong intramolecular acceptor hydrogen bonds with the adjacent 4'-hydroxyl. The compounds studied showed no differences in their relative affinities for heart and liver nuclei, suggesting that receptors in these tissues are similar. However, the relationships between thyromimetic activity (induction of GPDH) and nuclear binding showed some tissue differences. A high correlation between activity and binding is observed for full agonists in the heart, but an equally significant correlation for the liver data is only seen when 3'-substituent bulk (molar refractivity) is included in the analysis. These results suggest the possibility that differential tissue penetration or access to receptors may occur in vivo.
• Ruthenium-Catalyzed Reductive Amidation without an External Hydrogen Source
  作者：Niyaz Z. Yagafarov、Karim M. Muratov、Klim Biriukov、Dmitry L. Usanov、Olga Chusova、Dmitry S. Perekalin、Denis Chusov

  DOI：10.1002/ejoc.201701527

  日期：2018.1.31

  A catalytic system for the atom‐economical Ru‐catalyzed reductive amidation of aldehydes was developed. A cyclopentadienyl ruthenium catalyst was employed in this process with loadings as low as 0.5–1 mol‐%, and carbon monoxide was used as the deoxygenative agent. A number amides and aromatic aldehydes were able to successfully afford the corresponding secondary amide in yields of 79–84 %.

  开发了原子经济的Ru催化的醛还原酰胺化反应的催化体系。在此过程中使用了环戊二烯基钌催化剂，其负载量低至0.5-1 mol％，一氧化碳用作脱氧剂。许多酰胺和芳香醛能够成功获得相应的仲酰胺，收率为79–84％。