3,4-bis(phenylthio)-3-sulfolene | 102058-95-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3,4-bis(phenylthio)-3-sulfolene
• 英文别名: 3,4-Bis-(phenylthio)-2,5-dihydrothiophene-1,1-dioxide；3,4-bis(phenylsulfanyl)-2,5-dihydrothiophene 1,1-dioxide
• CAS: 102058-95-7
• 化学式: C₁₆H₁₄O₂S₃
• 分子量: 334.484
• InChiKey: PLDCVFLSCIUITG-UHFFFAOYSA-N

物化性质

• 熔点：
  72-74 °C
• 沸点：
  552.6±50.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  93.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-bis(phenylthio)-3-sulfolene 以 氘代甲苯 为溶剂， 反应 1.0h， 生成 2,3-bis(phenylthio)-1,3-butadiene
  参考文献：
  名称：

  Lucchi, Ottorino de; Marchioro, Gaetano, Phosphorus and Sulfur and the Related Elements, 1985, vol. 24, p. 305 - 310

  摘要：

  DOI：
• 作为产物：
  描述：

  3-thiophenyl-3-sulfolene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 7.0h， 生成 3,4-bis(phenylthio)-3-sulfolene
  参考文献：
  名称：

  Preparation of 2,3-dihetero-substituted 1,3-dienes from brominated 2-sulfolenes

  摘要：

  DOI：

  10.1021/jo00248a023

文献信息

• Aza-Diels–Alder reactions and synthetic applications of thio-substituted 1,3-dienes with arylsulfonyl isocyanates
  作者：Shang-Shing P. Chou、Chia-Cheng Hung

  DOI：10.1016/s0040-4039(00)01447-7

  日期：2000.10

  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 regio- and chemoselectivity. The cyclized products 3a and 4 underwent further interesting reactions with nucleophiles and bases to give useful heterocyclic compounds.

  芳基磺酰基异氰酸酯与硫取代的1,3-二烯经3-环丁烯前体1的第一次氮杂-狄尔斯-阿尔德反应使环化产物3完全控制了区域选择性和化学选择性。环化产物3a和4与亲核试剂和碱进行进一步有趣的反应，得到有用的杂环化合物。
• 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。
• Comparison of the effects of sulphenyl, sulphinyl, and sulphonyl substituents on diene reactivity and regioselectivity in the Diels–Alder reaction
  作者：Shang-Shing P. Chou、Der-Jen Sun

  DOI：10.1039/c39880001176

  日期：——

  The Diels–Alder reactions of 2-phenylthiobuta-1,3-dienes with PhS, PhSO, and PhSO2 groups in position 3 indicate that both reactivity and regioselectivity follow the order PhS > PhSO > PhSO2.

  2-苯基硫丁1，3-二烯与3位上的PhS，PhSO和PhSO 2基团的Diels-Alder反应表明，反应性和区域选择性均遵循PhS> PhSO> PhSO 2的顺序。
• Dianilinophthalimides: Potent and Selective, ATP-Competitive Inhibitors of the EGF-Receptor Protein Tyrosine Kinase
  作者：Uwe Trinks、Elisabeth Buchdunger、Pascal Furet、Wilhelm Kump、Helmut Mett、Thomas Meyer、Marcel Mueller、Urs Regenass、Greti Rihs

  DOI：10.1021/jm00033a019

  日期：1994.4

  Dianilinophthalimides represent a novel class of inhibitors of the EGF-receptor protein tyrosine kinase with a high degree of selectivity versus other tyrosine and serine/threonine kinases. Steady-state kinetic analysis of compound 3, which showed potent inhibitory activity, revealed competitive type kinetics relative to ATP. Despite a highly symmetrical structure of compound 3, X-ray studies revealed an unsymmetrical propeller-shaped conformation of the molecule which differs clearly from that of the constitutionally related staurosporine aglycons. These conformational differences may explain the reversal of the selectivity profile of compound 3 relative to the staurosporine aglycons. In cellular assays compounds 3 and 4 have been shown to inhibit EGF-induced receptor autophosphorylation, c-fos induction and EGF-dependent proliferation of Balb/ c MK cells. This inhibition was selective as compounds had no effect on PDGF-induced receptor autophosphorylation and c-fos induction. Furthermore, compound 3 showed potent antitumor activity in vivo at well-tolerated doses.
• Chou, Shang-Shing P.; Sun, Der-Jen; Tai, Hai-Ping, Journal of the Chinese Chemical Society, 1995, vol. 42, # 5, p. 809 - 814
  作者：Chou, Shang-Shing P.、Sun, Der-Jen、Tai, Hai-Ping

  DOI：——

  日期：——