2-Methyl-2-(4-biphenylyl)-1,3-dithiolane | 120825-00-5

• 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: 2-Methyl-2-(4-biphenylyl)-1,3-dithiolane
• 英文别名: 2-biphenyl-4-yl-2-methyl-1,3-dithiolane；2-Methyl-2-(4-phenylphenyl)-1,3-dithiolane
• CAS: 120825-00-5
• 化学式: C₁₆H₁₆S₂
• 分子量: 272.435
• InChiKey: IPIAHWWNRREVDH-UHFFFAOYSA-N

物化性质

• 沸点：
  418.3±45.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Methyl-2-(4-biphenylyl)-1,3-dithiolane 在 N-溴代丁二酰亚胺(NBS) 、 叠氮化四丁基铵 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以70%的产率得到5-Azido-6-biphenyl-4-yl-2,3-dihydro-[1,4]dithiine
  参考文献：
  名称：

  由亲电试剂引发的 1,3-Dithiolanes 和 1,3-Dithianes 的轻松扩环取代反应生成 Monohalo-、-cyano-、-azido- 和 -thiocyanato-1,4-dithiins 和 -1,4-dithiepins

  摘要：

  报告了使用不同亲电试剂从不同芳基甲基酮生成 1,3-二硫戊环和 1,3-二噻烷的高产环扩张取代反应的温和方便的方法。在这项研究中，描述了 monohalo-、-cyano-、-azido-、-thiocyanato-1,4-dithiins 和 -1,4-dithiepins 的简便制备。还提出了本文中描述的反应的一般机制。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  DOI：

  10.1002/ejoc.200400502

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。
• Nickel-catalysed coupling of dithioacetals with silylmethylmagnesium chloride. A simple synthesis of allylsilanes
  作者：Zhi-Jie Ni、Tien-Yau Luh

  DOI：10.1039/c39880001011

  日期：——

  Allylsilanes are conveniently synthesized from the reaction of dithioacetals of ketones with trimethylsilylmethylmagnesium chloride.

  烯丙基硅烷是由酮的二硫缩醛与三甲基甲硅烷基甲基镁氯化物的反应方便地合成的。
• Nickel-catalyzed olefination of cyclic benzylic dithioacetals by Grignard reagents. Scope and mechanism
  作者：Zhi Jie Ni、Nai Wen Mei、Xian Shi、Yih Ling Tzeng、Maw Cherng Wang、Tien Yau Luh

  DOI：10.1021/jo00012a043

  日期：1991.6

  The details of the first nickel-catalyzed olefination of cyclic dithioacetals to form substituted styrenes and aryl-substituted 1,4-pentadienes are described. The reaction represents a new synthetic use of the dithioacetal functionality. Only nickel complexes catalyzed these cross-coupling reactions; palladium complexes displayed no catalytic activity under the reaction conditions employed. Selective coupling occurred. A mechanism for the reaction is proposed. The experimental evidence indicates that, in these nickel-catalyzed couplings, cyclic dithioacetals are more reactive than their acyclic analogues. This increased reactivity appears to be the result of maintaining the two sulfur atoms in close proximity to each other by the use of a short chain of methylene groups.
• MOLYBDENUM PENTACHLORIDE (MOCL_s) PROMOTES EFFICIENT RING-EXPANSION AND RING-EXPANSION-CHLORINATION OF 1,3-DITHIOLANES AND 1,3-DITHIANES IN THE PRESENCE OF DMSO. PART 3^l
  作者：Habib Firouzabadi、Babak Karimi

  DOI：10.1080/10426500108040268

  日期：2001.8

  Ring-expansion and ring-expansion-chlorination of 1,3-dithiolanes and dithianes conducted in the presence of MoCl5 and DMSO are described.