2-But-3-enyl-4-phenylsulfanyl-2,5-dihydrothiophene 1,1-dioxide | 197862-42-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-But-3-enyl-4-phenylsulfanyl-2,5-dihydrothiophene 1,1-dioxide
• CAS: 197862-42-3
• 化学式: C₁₄H₁₆O₂S₂
• 分子量: 280.412
• InChiKey: CLSGDOXPUQIYKZ-UHFFFAOYSA-N

物化性质

• 沸点：
  470.0±45.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-But-3-enyl-4-phenylsulfanyl-2,5-dihydrothiophene 1,1-dioxide 在 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 双氧水 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 4-(1,1-Dioxo-4-phenylsulfanyl-2,5-dihydrothiophen-2-yl)butanal
  参考文献：
  名称：

  硝酮与硫取代的二烯的分子内环加成反应及其合成应用

  摘要：

  从3-环丁烯前体方便地制备了一系列硫取代的二烯基硝基酮。分子内的1，3-偶极环加成反应得到稠合的双环异恶唑烷。已经研究了这些反应的区域和立体化学结果以及合成应用。

  DOI：

  10.1016/s0040-4039(97)01037-x
• 作为产物：
  描述：

  3-thiophenyl-3-sulfolene 、 4-碘-1-丁烯 在 六甲基磷酰三胺 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以74%的产率得到2-But-3-enyl-4-phenylsulfanyl-2,5-dihydrothiophene 1,1-dioxide
  参考文献：
  名称：

  硝酮与硫取代的二烯的分子内环加成反应及其合成应用

  摘要：

  从3-环丁烯前体方便地制备了一系列硫取代的二烯基硝基酮。分子内的1，3-偶极环加成反应得到稠合的双环异恶唑烷。已经研究了这些反应的区域和立体化学结果以及合成应用。

  DOI：

  10.1016/s0040-4039(97)01037-x

文献信息

• Synthesis of sulfur-substituted quinolizidines and pyrido[1,2-a]azepines by ring-closing metathesis
  作者：Shang-Shing P. Chou、Chu-Fang Liang、Tse-Ming Lee、Chih-Fen Liu

  DOI：10.1016/j.tet.2007.05.104

  日期：2007.8

  Sulfur-substituted quinolizidines and pyrido[1,2-a]azepines (7) can be prepared by ring-closing metathesis (RCM) of 4-(phenylthio)-1,2,5,6-tetrahydropyridin-2-ones (6) bearing terminal alkenyl groups at both N-1 and C-6 positions, which are obtained from 3-(phenylthio)-3-sulfolene (1) in four steps. Some synthetic transformations of 2-(phenylthio)-1,6,9,9a-tetrahydroquinolizin-4-one (7a) and 2-(phenylthio)-1

  可以通过4-（苯硫基）-1,2,5,6-四氢吡啶-2--2-酮的闭环复分解（RCM）制备硫取代的喹quin嗪和吡啶并[1,2- a ]氮杂pine（7）（6））在N-1和C-6位置均带有末端烯基，它们是由3-（苯硫基）-3-环丁砜（1）分四个步骤制得的。2-（苯硫基）-1,6,9,9a-四氢喹啉嗪-4-one（7a）和2-（苯硫基）-1,6,9,10,10a-五氢吡啶并[1,2- a]的一些合成转化还报道了] azepin-4-one（7d）。
• Synthesis of 6-substituted tetrahydropyridinones and cyclization to indolizidine and quinolizidine structures
  作者：Shang-Shing P. Chou、Hao-Chieh Chiu、Chia-Cheng Hung

  DOI：10.1016/s0040-4039(03)01096-7

  日期：2003.6

  3-Sulfolenes 1 with various substituents at C-2 underwent [4+2] cycloaddition reactions with p-toluenesulfonyl isocyanate to give the teterahydropyridinones 4. Through N-detosylation and Hg(II)-mediated electrophilic addition/intramolecular cyclization of 4e and 4f, the indolizidine and quinolizidine compounds 7a/7b and 8 were synthesized, respectively.

  在C-2处具有各种取代基的3-Sulfolenes 1与对甲苯磺酰基异氰酸酯进行[4 + 2]环加成反应，得到四氢吡啶并酮4。通过N-去甲苯基化和Hg（II）介导的4e和4f的亲电加成/分子内环化反应，分别合成了吲哚并咪唑和喹唑烷化合物7a / 7b和8。
• Intramolecular Cycloaddition of Nitrones and Nitrile Oxides with Sulfur-Substituted Dienes and Its Synthetic Applications
  作者：Shang-Shing P. Chou、Yu-Ju Yu

  DOI：10.1002/jccs.199800028

  日期：1998.2

  AbstractA series of sulfur‐substituted dienyl nitrones and oximes were conveniently prepared from the 3‐sulfolene precursors. Regiospecific intramolecular 1,3‐dipolar cycloadditions of nitrones and nitrile oxides with sulfur‐substituted dienes have been efficiently carried out from the suitable 3‐sulfolene precursors. The stereochemistry of the cycloaddition of nitrones depends on the structure of the substituent (sulfide or sulfone) on the diene as well as on the chain length connecting the diene and nitrone. The fused bicyclic products obtained from these reactions have been converted to some interesting heterocyclic compounds which have the useful structure of vinyl sulfide or sulfone.
• Intramolecular Diels-Alder Reactions of Thio-Substituted Dienes with Enones
  作者：Shang-Shing P. Chou、Yu-Ju Yu

  DOI：10.1002/jccs.199700055

  日期：1997.8

  AbstractThio‐substituted dienes bearing an enone moiety were readily prepared from 3‐sulfolenes, and their intramolecular Diels‐Alder (IMDA) reactions were studied. Octahydronaphthalenones were produced in good yield with high stereoselectivity. Hexahydroindenones were also obtained, but the stereoselectivity was lower.
• Tandem cross metathesis and intramolecular aza-Michael reaction to synthesize bicyclic piperidines and indolizidine 167E
  作者：Shang-Shing P. Chou、Jhih-Liang Huang

  DOI：10.1016/j.tetlet.2012.08.031

  日期：2012.10

  We have successfully transformed the terminal alkenes of dihydropyridones to the alpha,beta-unsaturated esters by cross metathesis (CM). After detosylation the secondary amides can undergo the intramolecular aza-Michael reaction to give the bicyclic piperidine structures. The stereoselectivity of the aza-Michael reaction is determined by the size of the newly formed ring. With simple transformations we have also achieved the synthesis of indolizidine 167E. (C) 2012 Elsevier Ltd. All rights reserved.