3,4-dimethyl-6-phenyl-5,6-dihydro-2H-thiopyran | 84040-18-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫吡喃类
• 英文名称: 3,4-dimethyl-6-phenyl-5,6-dihydro-2H-thiopyran
• 英文别名: 3,6-dihydro-4,5-dimethyl-2-phenyl-2H-thiopyran；4,5-dimethyl-2-phenyl-3,6-dihydro-2H-thiopyran；2-phenyl-4,5-dimethyl-1-thiocyclohex-4-ene
• CAS: 84040-18-6
• 化学式: C₁₃H₁₆S
• 分子量: 204.336
• InChiKey: WZYNLGKPOWLKLX-UHFFFAOYSA-N

物化性质

• 沸点：
  130-135 °C(Press: 0.4 Torr)
• 密度：
  1.024±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,4-dimethyl-6-phenyl-5,6-dihydro-2H-thiopyran 、 间氯过氧苯甲酸 生成 trans-6-phenyl-3,4-dimethyl-5,6-dihydro-2H-thiopyran S-oxide
  参考文献：
  名称：

  BONINI B. F.; MAZZANTI G.; ZANI P.; MACCAGNANI G.; BARBARO G.; BATTAGLIA +, J. CHEM. SOC. CHEM. COMMUN.,(1986) N 12, 964-965

  摘要：

  DOI：
• 作为产物：
  描述：

  硫代苯甲酰三苯基硅烷 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 30.0h， 生成 3,4-dimethyl-6-phenyl-5,6-dihydro-2H-thiopyran
  参考文献：
  名称：

  Bonini, Bianca F.; Lenzi, Alberto; Maccagnani, Gaetano, Journal of the Chemical Society. Perkin transactions I, 1987, p. 2643 - 2646

  摘要：

  DOI：

文献信息

• Reactions of Wittig Reagents with Episulfides or Elemental Sulfur
  作者：Kentaro Okuma、Yuji Tachibana、Jun-ichi Sakata、Takashi Komiya、Isao Kaneko、Yasuo Komiya、Yusuke Yamasaki、Shin-ichi Yamamoto、Hiroshi Ohta

  DOI：10.1246/bcsj.61.4323

  日期：1988.12

  The reactions of Wittig reagents with episulfides gave symmetrical olefins and triphenylphosphine sulfide in moderate yields. The same olefins were obtained by reactions of Wittig reagents with elemental sulfur. These reactions might proceed through thiocarbonyl intermediates, the existence of which was confirmed by Diels–Alder reactions with dienes.

  Wittig 试剂与环硫化物的反应以中等产率得到对称的烯烃和硫化三苯基膦。通过 Wittig 试剂与元素硫反应获得相同的烯烃。这些反应可能通过硫代羰基中间体进行，硫代羰基中间体的存在已通过与二烯的 Diels-Alder 反应证实。
• Ionic liquids as an alternative reaction medium for HMDST based synthesis of thioaldehydes
  作者：Damiano Tanini、Andrea Angeli、Antonella Capperucci

  DOI：10.1080/10426507.2015.1114487

  日期：2016.2.1

  Abstract Reaction of bis(trimethylsilyl)sulfide (HMDST) with aldehydes can be efficiently carried out in various ionic liquids, under CoCl2.6H2O or TfOTMF catalysis, leading to the formation of thioaldehydes, which are trapped as Diels-Alder cycloadducts. When 1,3-cycloheaxadiene was used, a stereoselective entry to the endo isomer was always obtained.

  图形摘要摘要 双（三甲基甲硅烷基）硫化物 (HMDST) 与醛的反应可以在 CoCl2·6H2O 或 TfOTMF 催化下在各种离子液体中有效地进行，导致硫醛的形成，硫醛被作为 Diels-Alder 环加合物捕获。当使用 1,3- 环己二烯时，总是能立体选择性地进入内异构体。
• Synthesis and isolation of aryl thioaldehyde S-oxides
  作者：Bianca F. Bonini、Germana Mazzanti、Paolo Zani、Gaetano Maccagnani、Gaetano Barbaro、Arturo Battaglia、Patrizia Giorgianni

  DOI：10.1039/c39860000964

  日期：——

  (E)-Phenyl and (E)-(p-tolyl) trimethylsilyl thioketone S-oxides can be easily and stereospecifically protodesilylated into the corresponding (Z)-aryl thioaldehyde S-oxides; these stable liquid lachrimatory compounds show good reactivity as heterodienophiles and the reaction with 1,3-dienes is surprisingly non-stereospecific.

  （E）-苯基和（E）-（对甲苯基）三甲基甲硅烷基硫代酮S-氧化物可以容易地和立体定向地被去甲硅烷基化为相应的（Z）-芳基硫代醛S-氧化物；这些稳定的液体催泪性化合物表现出良好的作为异二烯亲和性的反应性，并且与1，3-二烯的反应令人惊讶地是非立体特异性的。
• REACTIONS OF 2,4,6-TRIARYL-DIHYDRO-1,3,5-DITHIAZINES WITH ELECTROPHILIC REAGENTS
  作者：Yuji Takikawa、Kazuaki Shimada、Takahiro Makabe、Saburo Takizawa

  DOI：10.1246/cl.1983.1503

  日期：1983.10.5

  2,4,6-Triaryl-dihydro-1,3,5-dithiazines reacted with electrophilic reagents such as p-TsOH·H2O, CF3COOH, HCl, and BF3·OEt2 under reflux in CH3CN to afford α-2,4,6-triaryl-1,3,5-trithianes and β-isomers (3a-d) in good yields. Reactions with I2 gave selectively 3a-d in high yields, while with ICl or IBr gave 3a-d and p-substituted benzylideneamine·HY.

  2,4,6-三芳基-二氢-1,3,5-二噻嗪与亲电试剂如 p-TsOH·H2O、CF3COOH、HCl 和 BF3·OEt2 在 CH3CN 中回流反应得到 α-2,4,6 -triaryl-1,3,5-trithianes 和 β-异构体 (3a-d) 的产率很高。与 I2 反应以高产率选择性地得到 3a-d，而与 ICl 或 IBr 反应得到 3a-d 和对位取代的亚苄基胺·HY。
• The generation and trapping of thiobenzaldehyde and thioacetaldehyde
  作者：Jack E. Baldwin、R. C. Gerald Lopez

  DOI：10.1039/c39820001029

  日期：——

  thioacetaldehyde have been generated by thermolysis of alkyl thiosulphinates under preparatively useful conditions and trapped with aromatic and aliphatic 1,3-dienes, the adducts with anthracene being convenient and high yielding sources of such thioaldehydes; thiobenzaldehyde has been shown to undergo the ‘ene’ reaction.

  硫代苯甲醛和硫代乙醛是通过在制备上有用的条件下热解烷基硫代硫酸盐而生成的，并被芳族和脂族的1,3-二烯捕获，蒽的加合物是此类硫代醛的方便且高收率的来源。已证明硫代苯甲醛会发生“烯”反应。