2-phenyl-1-phenoxycarbonyl-1,2-dihydropyridine | 95895-18-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-phenyl-1-phenoxycarbonyl-1,2-dihydropyridine
• 英文别名: phenyl 2-phenylpyridine-1(2H)-carboxylate；phenyl 2-phenyl-1(2H)-pyridinecarboxylate；phenyl 2-phenyl-2H-pyridine-1-carboxylate
• CAS: 95895-18-4
• 化学式: C₁₈H₁₅NO₂
• 分子量: 277.323
• InChiKey: MGDFHWPBYUKJGS-UHFFFAOYSA-N

物化性质

• 沸点：
  427.5±45.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-phenyl-1-phenoxycarbonyl-1,2-dihydropyridine 在 sodium tetrahydroborate 、 (S)-1-hydroxy-3,3-dimethyl-1,1-diphenylbutan-2-amininium trifluoroacetate 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 49.0h， 生成 (1S,3S,4S,7S)-7-hydroxymethyl-3-phenyl-2-phenoxycarbonyl-2-azabicyclo[2.2.2]oct-5-ene
  参考文献：
  名称：

  Enantioselective Diels–Alder Reaction of 1,2-Dihydropyridines with Aldehydes Using β-Amino Alcohol Organocatalyst

  摘要：

  The enantioselective Diels Alder reaction of 1,2-dihydropyridines with aldehydes using an easily prepared optically active beta-amino alcohol catalyst was found to provide optically active isoquinuclidines, an efficient synthetic intermediate of pharmaceutically important compounds such as oseltamivir phosphate, with a satisfactory chemical yield and enantioselectivity (up to 96%, up to 98% ee). In addition, the obtained highly optically pure isoquinuclidine was easily converted to an optically active piperidine having four successive carbon centers.

  DOI：

  10.1021/jo501433c
• 作为产物：
  描述：

  三甲基(4-吡啶基)锡 生成 2-phenyl-1-phenoxycarbonyl-1,2-dihydropyridine
  参考文献：
  名称：

  Regioselective addition of nucleophiles to 1-(phenoxycarbonyl)-3-trialkylstannylpyridinium salts

  摘要：

  DOI：

  10.1016/s0040-4039(01)80982-5

文献信息

• Synthesis of bicyclic tetrahydropyridine enamides and enecarbamates by hetero-Cope rearrangement of nitroso cycloadducts
  作者：Francesco Berti、Andrea Menichetti、Valeria Di Bussolo、Lucilla Favero、Mauro Pineschi

  DOI：10.1007/s10593-018-2289-8

  日期：2018.4

  The hetero-Cope rearrangement reactions of inverse carbamate and amide nitroso Diels–Alder cycloadducts with 1,2-dihydropyridines to give novel tetrahydropyridine enamides and enecarbamates have been studied in detail identifying optimal reaction conditions. The possibility to obtain tetrahydropyridine enamides and carbamates containing a free OH at the C-4 position is restricted to only particular

  氨基甲酸酯和酰胺亚硝基Diels-Alder环加成物与1,2-二氢吡啶的杂Cope重排反应可得到新颖的四氢吡啶烯酰胺和烯氨基甲酸酯，详细研究了最佳反应条件。当处理氨基甲酸酯亚硝基环加合物时，获得在C-4位上含有游离OH的四氢吡啶酰胺和氨基甲酸酯的可能性仅限于特定的取代方式。另一方面，从容易获得的酰胺亚硝基环加合物和催化量的亚铜盐开始，现在可以得到几种取代的4a，7,8a-四氢吡啶并[4,3- e ]-[1,4,2]二恶嗪产量中等至良好。
• Synthesis and synthetic utility of 1-acyl-2-alkyl-4-trimethylstannyl-1,2-dihydropyridines
  作者：Daniel L. Comins、Abdul H. Abdullah、Nathan B. Mantlo

  DOI：10.1016/s0040-4039(01)91245-6

  日期：1984.1
• COMINS, D. L.;ABDULLAH, A. H.;MANTLO, N. B., TETRAHEDRON LETT., 1984, 25, N 43, 4867-4870
  作者：COMINS, D. L.、ABDULLAH, A. H.、MANTLO, N. B.

  DOI：——

  日期：——
• COMINS D. L.; MANTLO N. B., TETRAHEDRON LETT., 28,(1987) N 7, 759-762
  作者：COMINS D. L.、 MANTLO N. B.

  DOI：——

  日期：——
• Enantioselective Diels–Alder Reaction of 1,2-Dihydropyridines with Aldehydes Using β-Amino Alcohol Organocatalyst
  作者：Yoshihito Kohari、Yuko Okuyama、Eunsang Kwon、Taniyuki Furuyama、Nagao Kobayashi、Teppei Otuki、Jun Kumagai、Chigusa Seki、Koji Uwai、Gang Dai、Tatsuo Iwasa、Hiroto Nakano

  DOI：10.1021/jo501433c

  日期：2014.10.17

  The enantioselective Diels Alder reaction of 1,2-dihydropyridines with aldehydes using an easily prepared optically active beta-amino alcohol catalyst was found to provide optically active isoquinuclidines, an efficient synthetic intermediate of pharmaceutically important compounds such as oseltamivir phosphate, with a satisfactory chemical yield and enantioselectivity (up to 96%, up to 98% ee). In addition, the obtained highly optically pure isoquinuclidine was easily converted to an optically active piperidine having four successive carbon centers.