N-丁基-1-萘甲酰胺 | 54751-78-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: N-丁基-1-萘甲酰胺
• 英文名称: naphthalene-1-carboxylic acid butylamide
• 英文别名: N-butyl-1-naphthamide；N-butylnaphthalene-1-carboxamide
• CAS: 54751-78-9
• 化学式: C₁₅H₁₇NO
• 分子量: 227.306
• InChiKey: YSXQPIVYBHSMBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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-丁基-1-萘甲酰胺 在 甲醇 、 potassium polysulfide 、 potassium formate 作用下， 以 二甲基亚砜 为溶剂， 以67 %的产率得到N-butyl-1,4-dihydronaphthalene-1-carboxamide
  参考文献：
  名称：

  通过多硫阴离子和甲酸之间的光驱动相互作用实现（杂）芳烃的脱芳构化**

  摘要：

  开发了一种光催化方案，通过在甲醇存在下光激发多硫化物阴离子的单电子转移诱导的自由基-极性交叉机制，用于取代萘、吲哚和相关杂芳族化合物的脱芳构化。催化转化通过多硫化物自由基阴离子和甲酸盐之间的氢原子转移来维持。

  DOI：

  10.1002/anie.202309764
• 作为产物：
  描述：

  naphthalen-1-yl pivalate 、 异氰酸正丁酯 在 1,1'-双(二苯基膦)二茂铁 、 dipotassium hydrogenphosphate 、 氯化镍二甲氧基乙烷 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以48%的产率得到N-丁基-1-萘甲酰胺
  参考文献：
  名称：

  Ni-Catalyzed Direct Reductive Amidation via C–O Bond Cleavage

  摘要：

  A novel Ni-catalyzed reductive amidation of C(sp(2))-O and C(sp(3))-O electrophiles with isocyanates is described. This umpolung reaction allows for an unconventional preparation of benzamides using simple starting materials and easy-to-handle Ni catalysts.

  DOI：

  10.1021/ja5029793

文献信息

• <i>N</i>-Acylbenzotriazoles:  Neutral Acylating Reagents for the Preparation of Primary, Secondary, and Tertiary Amides
  作者：Alan R. Katritzky、Hai-Ying He、Kazuyuki Suzuki

  DOI：10.1021/jo000792f

  日期：2000.12.1

  Readily available N-acylbenzotriazoles 2a-q efficiently acylate aqueous ammonia and primary and secondary amines to give primary, secondary, and tertiary amides in good to excellent yields. The wide applicability of the procedure is illustrated by the preparation of (i) alpha-hydroxyamides from alpha-hydroxy acids and of (ii) perfluoroalkylated amides.

  易于获得的N-酰基苯并三唑2a-q有效地酰化氨水和伯胺和仲胺，从而以良好或优异的收率得到伯，仲和叔酰胺。该方法的广泛适用性通过（i）由α-羟基酸制备α-羟基酰胺和（ii）全氟烷基化酰胺来说明。
• Direct Transformation of Secondary Amides into Secondary Amines: Triflic Anhydride Activated Reductive Alkylation
  作者：Kai-Jiong Xiao、Ai-E Wang、Pei-Qiang Huang

  DOI：10.1002/anie.201204098

  日期：2012.8.13

  transformation has been developed (see scheme; 2‐F‐Py=2‐fluoropyridine; Tf=trifluorosulfonyl). The amines are synthesized in good yields and the ketimine intermediates can be isolated before the reduction. This method should find applications in the synthesis of nitrogen‐containing bioactive molecules and medicinal agents.

  通用且温和：已开发出标题转化的第一个通用方法（请参阅方案； 2-F-Py = 2-氟吡啶； Tf =三氟磺酰基）。胺以高收率合成，并且在还原前可以分离出酮亚胺中间体。该方法应在合成含氮生物活性分子和药物中找到应用。
• 5-Bromo-norborn-2-en-7-one derivatives as a carbon monoxide source for palladium catalyzed carbonylation reactions
  作者：China M. Payne、Kyulee Cho、David S. Larsen

  DOI：10.1039/c9ra06594f

  日期：——

  Norbornenone (5b), obtained from the reaction of 2,5-dimethyl-3,4-diphenylcyclopentadienone dimer (3) with bromomaleic anhydride (4b), provides an excellent base-triggered source of carbon monoxide for palladium-catalysed carbonylation reactions. Aminocarbonylation, ketoamide synthesis, and Suzuki–Miyaura reactions of aryl iodides carried out in a two-chamber reaction vessel gave good to excellent yields of

  由 2,5-二甲基-3,4-二苯基环戊二烯酮二聚体 ( 3 ) 与溴马来酸酐 ( 4b ) 反应获得的降冰片烯酮 ( 5b )为钯催化的羰基化反应提供了极好的碱触发一氧化碳源。在两室反应容器中进行的芳基碘化物的氨基羰基化、酮酰胺合成和 Suzuki-Miyaura 反应产生了良好的羰基化产物产率。
• PHARMACEUTICAL USE OF SUBSTITUTED AMIDES
  申请人：Andersen Henrik Sune

  公开号：US20090124598A1

  公开（公告）日：2009-05-14

  The use of substituted amides for modulating the activity of 11β-hydroxysteroid dehydrogenase type 1 (11βHSD1) and the use of these compounds as pharmaceutical compositions, are described. Also a novel class of substituted amides, their use in therapy, pharmaceutical compositions comprising the compounds, as well as their use in the manufacture of medicaments are described. The present compounds are modulators and more specifically inhibitors of the activity of 11βHSD1 and may be useful in the treatment of a range of medical disorders where a decreased intracellular concentration of active glucocorticoid is desirable.

  描述了使用替代酰胺来调节11β-羟基类固醇脱氢酶1（11βHSD1）活性以及将这些化合物用作药物组合物的用途。还描述了一类新型的替代酰胺，它们在治疗中的应用，包含这些化合物的药物组合物，以及它们在制造药物中的应用。目前的化合物是11βHSD1活性的调节剂，更具体地是抑制剂，并且可能在治疗一系列医学疾病中有用，其中降低细胞内活性糖皮质激素浓度是可取的。
• Pharmaceutical use of substituted amides
  申请人：Andersen Sune Henrik

  公开号：US20060111366A1

  公开（公告）日：2006-05-25

  The use of substituted amides for modulating the activity of 11β-hydroxysteroid dehydrogenase type 1 (11βHSD1) and the use of these compounds as pharmaceutical compositions, are described. Also a novel class of substituted amides, their use in therapy, pharmaceutical compositions comprising the compounds, as well as their use in the manufacture of medicaments are described. The present compounds are modulators and more specifically inhibitors of the activity of 11βHSD1 and may be useful in the treatment, prevention and/or prophylaxis of a range of medical disorders where a decreased intracellular concentration of active glucocorticoid is desirable.

  本文介绍了使用取代酰胺来调节11β-羟化甾体脱氢酶1型（11βHSD1）的活性以及将这些化合物用作制药组合物的方法。还介绍了一类新型的取代酰胺，它们在治疗中的应用、包含这些化合物的制药组合物以及它们在药物制剂制造中的应用。这些化合物是11βHSD1的调节剂，更具体地说是抑制剂，可用于治疗、预防和/或预防一系列需要降低活性糖皮质激素细胞内浓度的医学疾病。