(3-isocyanopyridin-4-yl)(phenyl)methanone | 1258538-88-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3-isocyanopyridin-4-yl)(phenyl)methanone
• 英文别名: (3-Isocyanopyridin-4-yl)-phenylmethanone
• CAS: 1258538-88-3
• 化学式: C₁₃H₈N₂O
• 分子量: 208.219
• InChiKey: FUYFHAXMBDZMCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3-isocyanopyridin-4-yl)(phenyl)methanone 在 selenium 、 sulfur 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 4-hydroxy-3-(2-methoxyethyl)-4-phenyl-3,4-dihydropyrido[3,4-d]pyrimidine-2(1H)-thione
  参考文献：
  名称：

  A Simple Synthesis of 4-Hydroxy-3,4-dihydropyrido[3,4-d]pyrimidine-2(1H)-thione Derivatives by the Reaction of 3-Isothiocyanatopyridin-4-yl Ketones with Primary Amines

  摘要：

  The reaction of aryl(3-isothiocyanatopyridin-4-yl)methanones, prepared easily from commercially available 3-aminopyridine, with primary amines at room temperature afforded 3-substituted 4-aryl-4-hydroxy-3,4-dihydropyrido[3,4-d]pyrimidine-2(1H)-thiones in good yields. These ketones could be converted to new tricyclic heterocyclic systems, 2,3-dihydro-5H-pyrido[3,4-d]thiazolo [3,2-a]pyrimidine and 3,4-dihydro-2H,6H-pyrido [3',4':4,5]-pyrimido[2,1-b] [1,3]thiazine, upon treatment with 2-bromoethanamine hydrobromide and 3-bromopropaneamine hydrobromide, respectively, in the presence two equivalents of triethylamine.

  DOI：

  10.3987/com-14-13058
• 作为产物：
  描述：

  N-(4-benzoylpyridin-3-yl)formamide 在 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 以59%的产率得到(3-isocyanopyridin-4-yl)(phenyl)methanone
  参考文献：
  名称：

  Synthesis of 2,4,8-Trisubstituted 1,7-Naphthyridines by the Reaction of 4-(1-Aryl-2-methoxyethenyl)-3-isocyanopyridines with Excess Organolithiums

  摘要：

  AbstractA convenient method for the synthesis of 2,4,8‐trisubstituted 1,7‐naphthyridines 6 by the reaction of (E)‐4‐(1‐aryl‐2‐methoxyethenyl)‐3‐isocyanopyridines 4, which could be easily prepared from commercially available 3‐aminopyridine via aroylation of lithium (4‐lithiopyridin‐3‐yl)pivalamide with N‐methoxy‐N‐methylbenzamides, with excess organolithiums has been developed.

  DOI：

  10.1002/hlca.201000214

文献信息

• Synthesis of 2,3-Diaryl-3H-pyrrolo[2,3-c]pyridin-3-ol Derivatives by the Reaction of Aryl(3-isocyanopyridin-4-yl)methanones with Aryl Grignard Reagents
  作者：Kazuhiro Kobayashi、Taketoshi Kozuki、Manami Konishi、Teruhiko Suzuki、Miyuki Tanmatsu、Hisatoshi Konishi

  DOI：10.1002/hlca.201100079

  日期：2011.7

  aryl(3‐isocyanopyridin‐4‐yl)methanones 1, easily prepared from commercially available pyridin‐3‐amine, with aryl Grignard reagents gave, after aqueous workup, 2,3‐diaryl‐3H‐pyrrolo[2,3‐c]pyridin‐3‐ols 2. These rather unstable alcohols were O‐acylated with Ac2O in pyridine in the presence of a catalytic amount of 4‐(dimethylamino)pyridine (DMAP) to afford the corresponding 2,3‐diaryl‐3H‐pyrrolo[2,3‐c]pyridin‐3‐yl

  由市售的吡啶-3-胺容易制得的芳基（3-异氰基吡啶-4-基）甲烷1与芳基格氏试剂反应，经过水处理后，得到2,3-二芳基-3 H-吡咯并[2， 3- ç ]吡啶-3-醇2。在催化量的4-（二甲氨基）吡啶（DMAP）存在下，在吡啶中将这些相当不稳定的醇与Ac 2 O进行O-酰化反应，得到相应的2,3-二芳基-3 H-吡咯[2,3- c ]吡啶-3-乙酸乙烯酯3的收率相对较高。