2-(4-Pentenyl)-4-(phenylthio)-3-sulfolene | 124243-68-1

• 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-(4-Pentenyl)-4-(phenylthio)-3-sulfolene
• 英文别名: 2-(Pent-4-en-1-yl)-4-(phenylsulfanyl)-2,5-dihydro-1H-1lambda~6~-thiophene-1,1-dione；2-pent-4-enyl-4-phenylsulfanyl-2,5-dihydrothiophene 1,1-dioxide
• CAS: 124243-68-1
• 化学式: C₁₅H₁₈O₂S₂
• 分子量: 294.439
• InChiKey: VIALQGSXNMSTER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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-(4-Pentenyl)-4-(phenylthio)-3-sulfolene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以70%的产率得到2-(4-Pentenyl)-4-(phenylsulfonyl)-3-sulfolene
  参考文献：
  名称：

  Intramolecular Diels-Alder reactions of sulfur-substituted dienes via 3-sulfolenes

  摘要：

  DOI：

  10.1021/jo00291a031
• 作为产物：
  描述：

  3-thiophenyl-3-sulfolene 、 5-碘-1-戊烯 在 六甲基磷酰三胺 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以75%的产率得到2-(4-Pentenyl)-4-(phenylthio)-3-sulfolene
  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 and Applications of Tetrahydro-2-pyridinones via aza-Diels-Alder Reactions of Thio-substituted 1,3-Dienes with Arylsulfonyl Isocyanates
  作者：Shang-Shing Chou、Chia-Cheng Hung

  DOI：10.1055/s-2001-18710

  日期：——

  The first aza-Diels-Alder reactions of arylsulfonyl isocyanates with thio-substituted 1,3-dienes via the 3-sulfolene precursors 1 gave the cyclized products 3 with complete control of chemo- and regioselectivity. The cyclized products 3a and 5 underwent further reactions with nucleophiles and bases to give useful heterocyclic compounds. The N-tosyl group of the cyclic products could be selectively replaced by hydrogen or another substituent.

  芳基磺酰基异氰酸与硫取代的1,3-二烯通过3-砜基烯前体1进行的首批aza-Diels-Alder反应，完全控制了化学选择性和区域选择性地得到了环化产物3。环化产物3a和5与亲核试剂和碱进一步反应，生成了有用的杂环化合物。环状产物的N-对甲苯磺酰基可以被选择性地替换为氢或其他取代基。
• 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.
• 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.
• CHOU, SHANG-SHING P.;WEY, SHIOW-JYI, J. ORG. CHEM., 55,(1990) N, C. 1270-1274
  作者：CHOU, SHANG-SHING P.、WEY, SHIOW-JYI

  DOI：——

  日期：——