3-(Penten-5-yl)-2(1H)-piperidinethione | 144633-11-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3-(Penten-5-yl)-2(1H)-piperidinethione
• 英文别名: 3-(Penten-5-yl)piperidine-2(1H)-thione；3-pent-4-enyl-piperidine-2-thione；3-Pent-4-enylpiperidine-2-thione
• CAS: 144633-11-4
• 化学式: C₁₀H₁₇NS
• 分子量: 183.318
• InChiKey: DJAKUKPDSYXTKU-UHFFFAOYSA-N

物化性质

• 沸点：
  255.7±23.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  44.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(Penten-5-yl)-2(1H)-piperidinethione 在 lithium aluminium tetrahydride 作用下， 以 乙二醇二甲醚 、 乙醚 为溶剂， 反应 2.0h， 生成 9-pent-4-enyl-3,6,7,8-tetrahydro-2H-pyrido<2,1-b><1,3>thiazine
  参考文献：
  名称：

  Generation of the Dihydro-5H-Thiazolo[3,2-a]pyridin-3-one Ring System by Proton Loss from Isothiomünchnones

  摘要：

  Dihydro-5H-thiazolo[3,2-a]pyridin-3-ones are easily generated by proton loss from isothiomunchnones. The closely related tetrahydro-2H-pyrido[2,1-b]-[1,3]thiazin-4-one ring system was prepared by treating piperidine-2-thione with acryloyl chloride. These cyclic S,N-ketene acetals undergo smooth reaction with different electrophiles in the presence of Lewis acids.

  DOI：

  10.3987/com-93-s32
• 作为产物：
  描述：

  5-碘-1-戊烯 在 劳森试剂 、 正丁基锂 作用下， 以 乙二醇二甲醚 为溶剂， 反应 12.0h， 生成 3-(Penten-5-yl)-2(1H)-piperidinethione
  参考文献：
  名称：

  Generation of the Dihydro-5H-Thiazolo[3,2-a]pyridin-3-one Ring System by Proton Loss from Isothiomünchnones

  摘要：

  Dihydro-5H-thiazolo[3,2-a]pyridin-3-ones are easily generated by proton loss from isothiomunchnones. The closely related tetrahydro-2H-pyrido[2,1-b]-[1,3]thiazin-4-one ring system was prepared by treating piperidine-2-thione with acryloyl chloride. These cyclic S,N-ketene acetals undergo smooth reaction with different electrophiles in the presence of Lewis acids.

  DOI：

  10.3987/com-93-s32

文献信息

• 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.
• 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.
• Padwa Albert, Zhang Zhijia J., Heterocycles, 37 (1994) N 1, S 441-459
  作者：Padwa Albert, Zhang Zhijia J.

  DOI：——

  日期：——
• Generation and cycloaddition reactions of transient alkyl-substituted anhydro-4-hydroxythiazolium hydroxides
  作者：Donald L. Hertzog、William R. Nadler、Zhijia J. Zhang、Albert Padwa

  DOI：10.1016/s0040-4039(00)61077-8

  日期：1992.9

  Transient alkyl-substituted anhydro-4-hydroxythiazolium hydroxides undergo efficient inter- and intramolecular cycloaddition to provide the corresponding 1,3-dipolar cycloadducts in high yield.