5-(4-nitrophenyl)-2,3-dihydro-1,4-dithiine | 59176-99-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(4-nitrophenyl)-2,3-dihydro-1,4-dithiine
• 英文别名: 2-(4-nitrophenyl)-5,6-dihydro-1,4-dithiin；5-(4-nitro-phenyl)-2,3-dihydro-[1,4]dithiine；1,4-Dithiin, 2,3-dihydro-5-(4-nitrophenyl)-
• CAS: 59176-99-7
• 化学式: C₁₀H₉NO₂S₂
• 分子量: 239.319
• InChiKey: ISJZYVNHUFYXQM-UHFFFAOYSA-N

物化性质

• 熔点：
  139-140 °C
• 沸点：
  426.3±45.0 °C(Predicted)
• 密度：
  1.385±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  96.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2R)-2-methyl-2-(4-nitrophenyl)-1,3-dithiolane 1-oxide 以50%的产率得到
  参考文献：
  名称：

  CHEN C. H., TETRAHEDRON LETT. , 1976, NO 1, 25-28

  摘要：

  DOI：

文献信息

• Tungsten Hexachloride (WCl₆) in the Presence of Dimethylsulfoxide Promoted Facile and Efficient One-Pot Ring Expansion-Chlorination Reactions of 1,3-Dithiolanes and 1,3-Dithianes
  作者：Habib Firouzabadi、Nasser Iranpoor、Babak Karimi

  DOI：10.1055/s-1999-2628

  日期：1999.4

  Tungsten hexachloride (WCl6) in the presence of DMSO could be efficiently used for the conversion of 1,3-dithiolanes and 1,3-dithianes to their corresponding chlorinated derivatives of dihydro-1,4-dithiin and dihydro-1,4-dithiepine in high yield, respectively.

  在DMSO存在下，六氯钨（WCl6）可高效用于1,3-二硫杂环戊烷和1,3-二硫杂环己烷分别转化为其相应的二氢-1,4-二硫杂环己烷和二氢-1,4-二硫杂苯衍生物，且产率较高。
• Reactions of Silica Chloride (SiO₂Cl)/DMSO, a Heterogeneous System for the Facile Regeneration of Carbonyl Compounds from Thioacetals and Ring-Expansion Annelation of Cyclic Thioacetals
  作者：Habib Firouzabadi、Nasser Iranpoor、Hassan Hazarkhani、Babak Karimi

  DOI：10.1021/jo016343c

  日期：2002.4.1

  Thioketals without enolizable hydrogens adjacent to a sulfur atom are converted easily to the corresponding ketones in high yields under similar reaction conditions. However, thioketals with enolizable methyl and methylene groups undergo ring-expansion reactions to afford 1,4-dithiepins and 1,4-dithiins in dry CH(2)Cl(2) at room temperature in good yields.

  二氧化硅（SiO（2）Cl）/ DMSO，作为一种非均相系统，已被有效地用于在室温下将CH3（2）Cl（2）中的硫缩醛脱保护成醛。在相似的反应条件下，没有可固结氢原子与硫原子相邻的噻酮金属很容易以高收率转化为相应的酮。但是，硫醇缩酮与可烯丙基的甲基和亚甲基基团经过扩环反应，在室温下以良好的收率在干燥的CH（2）Cl（2）中提供1,4-二硫平和1,4-二硫精。
• Rapid Method for the Ring Expansion of 1,3-Dithiolanes and 1,3-Dithianes with <i>tert</i>-Butyl Hypochlorite
  作者：K. Akamanchi、Nitin Arote、Vikas Telvekar

  DOI：10.1055/s-2005-921906

  日期：——

  A new method for the ring expansion of 1,3-dithiolanes and 1,3-dithianes to dihydro-1,4-dithiins and dihydro-1,4-dithiepines, respectively, using tert-butyl hypochlorite at room temperature is described. The salient features of the protocol include mild reaction conditions, very short reaction time, and high yield.

  描述了一种在室温下使用叔丁基次氯酸将 1,3-dithiolanes 和 1,3-dithianes 分别扩环为 dihydro-1,4-dithiins 和 dihydro-1,4-dithiepines 的新方法。该协议的显着特点包括温和的反应条件、极短的反应时间和高产率。
• New Applications of 2,4,6-Trichloro-1,3,5-triazine (TT) in Synthesis: Highly Efficient and Chemoselective Deprotection and Ring-Enlargement of Dithioacetals and Oxathioacetals
  作者：Babak Karimi、Hassan Hazarkhani

  DOI：10.1055/s-2003-42459

  日期：——

  Efficient deprotection of a wide variety of 1,3-dithioacetals and 1,3-oxathiolanes to the corresponding carbonyl compounds at room temperature using a combination of 2,4,6-trichloro-1,3,5-triazine (TT) and dimethyl sulfoxide (DMSO) was investigated. In this way, 1,3-oxathioacetals and 1,3-dithioacetals of enolizable ketones were converted to the corresponding 1,4-oxathiepine and 1,4-dithiepine derivatives, respectively.

  研究了一种有效去保护各种1,3-二硫代乙缩醛和1,3-噁噻烷的方法，使用2,4,6-三氯-1,3,5-三嗪（TT）和二甲基亚砜（DMSO）的组合，在室温下将其转化为相应的羰基化合物。通过这种方式，酮类的1,3-噻唑乙缩醛和1,3-二硫代乙缩醛分别转化为相应的1,4-噻吩啶和1,4-二噻吩衍生物。
• A one-pot synthesis of 1,4-dithiins and 1,4-benzodithiins from ketones using the recyclable reagent 1,1′-(ethane-1,2-diyl)dipyridinium bistribromide (EDPBT)
  作者：Siva Murru、Veerababurao Kavala、C.B. Singh、Bhisma K. Patel

  DOI：10.1016/j.tetlet.2006.12.003

  日期：2007.2

  the corresponding ketones in one-pot using the recyclable reagent, 1,1′-(ethane-1,2-diyl)dipyridinium bistribromide (EDPBT) is described. This method is mild, simple, environmentally benign and is applied successfully for the ring expansion of 1,3-dithiolane to 1,4-dithiins and the ring expansion associated with aromatisation of cyclic ketones with or without double bonds in the ring. The main feature

  描述了使用可循环使用的试剂1,1'-（乙烷-1,2-二基）双吡啶鎓溴化吡啶鎓（EDPBT）从一锅中从相应的酮中新颖地获得1,4-二硫辛和1,4-苯并二硫辛的方法。该方法温和，简单，对环境无害，可成功地用于1，3-二硫戊环扩环成1，4-二硫辛以及与环酮的芳构​​化相关的扩环，该环酮在环中带有或不带有双键。该方法的主要特征是EDPBT在1,3-二硫杂环戊烷的形成中起促进剂的作用，在扩环步骤中起试剂的作用。用过的试剂可以回收，再生和再利用。