9-methyl-2-oxo-9-pent-4-enyl-3-phenyl-7,8-dihydro-6H-pyrido[2,1-b][1,3]thiazin-5-ium-4-olate | 150989-48-3

• 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: 9-methyl-2-oxo-9-pent-4-enyl-3-phenyl-7,8-dihydro-6H-pyrido[2,1-b][1,3]thiazin-5-ium-4-olate
• CAS: 150989-48-3
• 化学式: C₂₀H₂₃NO₂S
• 分子量: 341.474
• InChiKey: YAIYJZOHMNRKSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  68.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-methyl-2-oxo-9-pent-4-enyl-3-phenyl-7,8-dihydro-6H-pyrido[2,1-b][1,3]thiazin-5-ium-4-olate 以 甲苯 、 xylene 为溶剂， 反应 21.0h， 生成 7a-Methyl-2-phenyl-1,2,6,7,7a,8,9,10-octahydro-5H-pyrido[3,2,1-ij]quinolin-3-one
  参考文献：
  名称：

  Intramolecular 1,4-dipolar cycloaddition of cross-conjugated heterocyclic betaines. A new route to hexahydrojulolidines and related peri-fused ring systems

  摘要：

  Alkenyl-substituted bicyclic anhydro-4-hydroxy-2-oxo-1,3-thiazinium hydroxides prepared from 3,3-disubstituted thiolactams and 1,3-bielectrophiles formed thermally-induced intramolecular cycloadducts which underwent loss of carbonyl sulfide, followed by a 1,5-hydrogen shift, to hexahydrojulolidines and related ring systems.

  DOI：

  10.1021/jo00071a007
• 作为产物：
  描述：

  3-甲基哌啶-2-酮 在 劳森试剂 、 正丁基锂 作用下， 以 乙醚 、 苯 为溶剂， 生成 9-methyl-2-oxo-9-pent-4-enyl-3-phenyl-7,8-dihydro-6H-pyrido[2,1-b][1,3]thiazin-5-ium-4-olate
  参考文献：
  名称：

  Intramolecular 1,4-dipolar cycloaddition of cross-conjugated heterocyclic betaines. A new route to hexahydrojulolidines and related peri-fused ring systems

  摘要：

  Alkenyl-substituted bicyclic anhydro-4-hydroxy-2-oxo-1,3-thiazinium hydroxides prepared from 3,3-disubstituted thiolactams and 1,3-bielectrophiles formed thermally-induced intramolecular cycloadducts which underwent loss of carbonyl sulfide, followed by a 1,5-hydrogen shift, to hexahydrojulolidines and related ring systems.

  DOI：

  10.1021/jo00071a007

文献信息

• Intramolecular 1,4-Dipolar Cycloadditions of Cross-Conjugated Heteroaromatic Betaines. Synthesis of Hexahydrojulolidines and Related Peri- and Ortho-Fused Ring Systems
  作者：Kevin T. Potts、Thevarak Rochanapruk、Albert Padwa、Steven J. Coats、Lazaros Hadjiarapoglou

  DOI：10.1021/jo00117a035

  日期：1995.6

  3-Alkenyl 2-lactams react with (chlorocarbonyl)phenylketene to give nonisolable anhydro-4-hydroxy-2-oxo-1,3-oxazinium hydroxides which undergo regio- and stereospecific 1,4-dipolar cycloaddition in moderate yields to produce cycloadducts containing a carbon dioxide bridge. Thermolysis of the cycloadduct led to extrusion of carbon dioxide via a nonconcerted 1,5-hydrogen shift to give julolidine-type derivatives. Two of the cycloadducts were characterized by single-crystal X-ray determinations. A significant enhancement in the overall yield of the cycloaddition occurred in related reactions using anhydro-4-hydroxy-2-oxo-1,3-thiazinium hydroxides obtained from 3-alkenyl-3-ethyl(or methyl) 2-thiolactams and a variety of 1,3-bielectrophiles such as (chlorocarbonyl)phenylketene, carbon suboxide, substituted malonyl dichlorides, and ethyl (chlorocarbonyl)acetate. The thiazinium betaines were often isolable, and in one instance, a single-crystal X-ray characterization was possible. Cycloaddition of the thiazinium betaines occurred in a regiospecific manner. The initially formed cycloadducts which retained the carbonyl sulfide bridge could be induced to lose COS on further heating. Julolidine-type derivatives were obtained principally via a nonconcerted process. Variation in lactam ring size, coupled with tether length and substituent in the 1,3-bielectrophile , enabled control of ring size, substituents, and whether an ortho- or peri-fused tricyclic system resulted from the overall cycloaddition. In contrast to the lactam system, the thiolactams require disubstitution in the 3-position to avoid proton loss in the intermediate betaine with formation of a 1,3-thiaioline-4,6-dione.
• Intramolecular 1,4-dipolar cycloaddition of cross-conjugated heterocyclic betaines. A new route to hexahydrojulolidines and related peri-fused ring systems
  作者：Kevin T. Potts、Thevarak Rochanapruk、Steven J. Coats、Lazaros Hadjiarapoglou、Albert Padwa

  DOI：10.1021/jo00071a007

  日期：1993.9

  Alkenyl-substituted bicyclic anhydro-4-hydroxy-2-oxo-1,3-thiazinium hydroxides prepared from 3,3-disubstituted thiolactams and 1,3-bielectrophiles formed thermally-induced intramolecular cycloadducts which underwent loss of carbonyl sulfide, followed by a 1,5-hydrogen shift, to hexahydrojulolidines and related ring systems.