6,6'-dimethylsulfinyl-2,2'-bipyridine | 1010071-43-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6,6'-dimethylsulfinyl-2,2'-bipyridine
• 英文别名: 2-Methylsulfinyl-6-(6-methylsulfinylpyridin-2-yl)pyridine
• CAS: 1010071-43-8
• 化学式: C₁₂H₁₂N₂O₂S₂
• 分子量: 280.371
• InChiKey: QHOVRYLPNQHXNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  98.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  6,6'-bis(methylsulfanyl)-2,2'-bipyridine 在 (+)-8,8-二氯樟脑磺哑嗪 作用下， 生成 6,6'-dimethylsulfinyl-2,2'-bipyridine
  参考文献：
  名称：

  6,6′-Dimethylsulfinyl-2,2′-bipyridine: crystal structure and Hirshfeld surface analysis

  摘要：

  The structure of 6,6'-dimethylsulfinyl-2,2'-bipyridine (1) has been determined by a single-crystal X-ray crystallography. This compound crystallizes in the monoclinic P2(1) space group with a = 5.7922(12) angstrom, b = 8.7292(5) angstrom, c = 13.0887(16) angstrom, beta = 102.094(14)degrees and Z = 2. The molecule of 1 consists of a 2,2'-bipyridine moiety substituted in the 6 and 6' positions by dimethylsulfinyl groups. Atoms belonging to one of these two groups are disordered over two positions with an occupation of 0.600(9) for the major component. The molecular structure of 1 has been compared and discussed with several similar compounds. In the solid state, molecules of 1 are linked by two independent weak C-H center dot center dot center dot O hydrogen bonds forming the infinite simple C(4) and C(5) chains, and their combined effect is a formation of the R-4(4)(42) ring additionally stabilized by intermolecular pi center dot center dot center dot pi stacking and S=O center dot center dot center dot pi interactions. Moreover, Hirshfeld surface analysis has been used for comparison of the interactions in the crystal structure of 1 and in those of several of its simple analogues [i.e. 1-[6-(6-acetylpyridin-2-yl)pyridin-2-yl]ethanone, dimethyl 2,2'-bipyridine-6,6'-dicarboxylate, 6,6'-dimethyl-2,2'-bipyridyl and 2,2'-bipyridyl].[GRAPHICS].

  DOI：

  10.1080/17415993.2013.799165
• 作为试剂：
  描述：

  丙烯基三氯硅烷 、 苯甲醛 在 6,6'-dimethylsulfinyl-2,2'-bipyridine 、 苄基三甲基溴化铵 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-1-苯基-3-丁烯-1-醇 、 (R)-1-Phenylbut-3-en-1-ol
  参考文献：
  名称：

  Synthesis of Enantiomerically Enriched Mono and Bis 2,2′-Bipyridine Alkyl Sulfoxides and Their First Application as Chiral Auxiliaries

  摘要：

  The direct asymmetric oxidation of 6,6'-bis(alkylsulfanyl)-2,2'-bipyridines 2a-e to non-racemic mono sulfoxides 3a-e and bis-sulfoxides 4a,c-e using either Davis oxaziridine or a modified Sharples reagent is reported. The use of isolated mono- and bis-sulfoxides as chiral auxiliaries was tested in either the asymmetric addition of the diethylzinc or allyl(trichloro)silane to benzaldehyde.

  DOI：

  10.1080/10426500902856347

文献信息

• The first approach to optically active 2,2′-bipyridine alkyl sulfoxides
  作者：Justyna Ławecka、Bogdan Bujnicki、Józef Drabowicz、Andrzej Rykowski

  DOI：10.1016/j.tetlet.2007.11.104

  日期：2008.1

  The synthesis of 6,6′-bis(alkylsulfanyl)-2,2′-bipyridines and their asymmetric oxidation to non-racemic 2,2′-bipyridine alkyl sulfoxides using either (+)-(8,8-dichlorocamphorylsulfonyl)oxaziridine or a modified Sharpless reagent is reported.

  6,6'-双（烷基硫烷基）-2,2'-联吡啶的合成及其使用（+）-（8,8-二氯樟脑磺酰基磺酰基）恶唑烷或不对称氧化为非外消旋的2,2'-联吡啶烷基亚砜报道了一种改良的Sharpless试剂。
• Synthesis of Enantiomerically Enriched Mono and Bis 2,2′-Bipyridine Alkyl Sulfoxides and Their First Application as Chiral Auxiliaries
  作者：Justyna Ławecka、Bogdan Bujnicki、Józef Drabowicz、Jerzy Łuczak、Andrzej Rykowski

  DOI：10.1080/10426500902856347

  日期：2009.5.14

  The direct asymmetric oxidation of 6,6'-bis(alkylsulfanyl)-2,2'-bipyridines 2a-e to non-racemic mono sulfoxides 3a-e and bis-sulfoxides 4a,c-e using either Davis oxaziridine or a modified Sharples reagent is reported. The use of isolated mono- and bis-sulfoxides as chiral auxiliaries was tested in either the asymmetric addition of the diethylzinc or allyl(trichloro)silane to benzaldehyde.
• 6,6′-Dimethylsulfinyl-2,2′-bipyridine: crystal structure and Hirshfeld surface analysis
  作者：Ewa Rozycka-Sokolowska、Bernard Marciniak、Justyna Ławecka、Bogdan Bujnicki、Jozef Drabowicz、Andrzej Rykowski

  DOI：10.1080/17415993.2013.799165

  日期：2013.12.1

  The structure of 6,6'-dimethylsulfinyl-2,2'-bipyridine (1) has been determined by a single-crystal X-ray crystallography. This compound crystallizes in the monoclinic P2(1) space group with a = 5.7922(12) angstrom, b = 8.7292(5) angstrom, c = 13.0887(16) angstrom, beta = 102.094(14)degrees and Z = 2. The molecule of 1 consists of a 2,2'-bipyridine moiety substituted in the 6 and 6' positions by dimethylsulfinyl groups. Atoms belonging to one of these two groups are disordered over two positions with an occupation of 0.600(9) for the major component. The molecular structure of 1 has been compared and discussed with several similar compounds. In the solid state, molecules of 1 are linked by two independent weak C-H center dot center dot center dot O hydrogen bonds forming the infinite simple C(4) and C(5) chains, and their combined effect is a formation of the R-4(4)(42) ring additionally stabilized by intermolecular pi center dot center dot center dot pi stacking and S=O center dot center dot center dot pi interactions. Moreover, Hirshfeld surface analysis has been used for comparison of the interactions in the crystal structure of 1 and in those of several of its simple analogues [i.e. 1-[6-(6-acetylpyridin-2-yl)pyridin-2-yl]ethanone, dimethyl 2,2'-bipyridine-6,6'-dicarboxylate, 6,6'-dimethyl-2,2'-bipyridyl and 2,2'-bipyridyl].[GRAPHICS].