2,6-dichloro-9-thiabicyclo[3.3.1]nonane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻烷
• 英文名称: 2,6-dichloro-9-thiabicyclo[3.3.1]nonane
• 英文别名: (1S,2S,5S,6S)-2,6-dichloro-9-thiabicyclo[3.3.1]nonane
• 化学式: C₈H₁₂Cl₂S
• 分子量: 211.155
• InChiKey: QUZIEYDEASXPSN-XAMCCFCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  2,6-dichloro-9-thiabicyclo[3.3.1]nonane 以 溶剂黄146 、 甲苯 为溶剂， 反应 4.0h， 生成 (1S,2R,5S,6R)-2,6-Bis-((Z)-dec-1-enyl)-9-thia-bicyclo[3.3.1]nonane
  参考文献：
  名称：

  Substitution reactions involving organoaluminum compounds

  摘要：

  DOI：

  10.1007/bf00956961
• 作为产物：
  描述：

  1,5-cis,cis-cyclooctadiene 在 sulfur monochloride 、 磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 2,6-dichloro-9-thiabicyclo[3.3.1]nonane
  参考文献：
  名称：

  2,6-Dichloro-9-thiabicyclo[3.3.1]nonane: Multigram Display of Azide and Cyanide Components on a Versatile Scaffold

  摘要：

  2,6-二氯-9-硫杂双环[3.3.1]壬烷可通过改进的二氯化硫、硫酰氯和 1,5- 环辛二烯缩合工艺轻易获得，它是一种性能良好的支架，可通过硫原子邻位基团的参与对叠氮化物和氰化物进行亲核取代。通过简单的萃取和洗涤程序，就能分离出产率高、纯度大于 95% 的产品。

  DOI：

  10.3390/11040212

文献信息

• Nucleophilic Substitution by Grignard Reagents on Sulfur Mustards
  作者：Antonella Converso、Pierre-Loïc Saaidi、K. Barry Sharpless、M. G. Finn

  DOI：10.1021/jo0489869

  日期：2004.10.1

  With proper activation of the leaving group, sulfur mustards react with Grignard reagents with neighboring group participation of the sulfur atom. 2,6-Dichloro-9-thiabicyclo[3.3.1]nonane is especially useful in this regard, providing clean reactivity with organomagnesium nucleophiles on a topologically constrained scaffold.

  通过离去基团的适当活化，硫芥子与格利雅试剂反应，硫原子的相邻基团参与其中。2，6-二氯-9-硫代双环[3.3.1]壬烷在这方面特别有用，可在拓扑受限的支架上提供与有机镁亲核试剂的清洁反应性。
• A Simple Method for the Preparation of <i>N</i>-Sulfonylsulfilimines from Sulfides
  作者：Andreas L. Marzinzik、K. Barry Sharpless

  DOI：10.1021/jo0012039

  日期：2001.1.1

  While excellent methods exist for the oxidation of sulfides to sulfoxides R1R2S-->R1R2SO, the azaversion of this atom transfer redox process, i.e., R1R2S-->R1R2S=N-SO2R3, has been less reliable. In sulfilimine synthesis, sulfoxide has been an inevitable byproduct in all cases to date, and the yields of sulfilimine have varied widely. A nearly ideal procedure for the sulfide to sulfonyl sulfilimine

  尽管存在将硫化物氧化为亚砜R1R2S-> R1R2SO的出色方法，但是这种原子转移氧化还原过程的氮杂转化，即R1R2S-> R1R2S = N-SO2R3，可靠性较差。迄今为止，在亚硫亚胺合成中，亚砜一直是不可避免的副产物，亚硫亚胺的收率变化很大。描述了将硫化物转化为磺酰基亚硫亚胺的几乎理想的方法。基本上通过简单地在乙腈中将它们一起搅拌，就可以从各种各样的硫化物和种类繁多的已知氯胺盐（R3SO2NClNa）的易于获得的磺酰基亚硝基化合物来源中获得几乎定量的产率。
• Photochemical and assisted cleavages of halo-9-thiabicyclononanes
  作者：Peter Heggison McCabe、Chine Isaac de Jenga、Angus Stewart

  DOI：10.1016/s0040-4039(01)81992-4

  日期：1981.1
• 2,6-Dichloro-9-thiabicyclo[3.3.1]nonane:  A Privileged, Bivalent Scaffold for the Display of Nucleophilic Components
  作者：Antonella Converso、Kristina Burow、Andreas Marzinzik、K. Barry Sharpless、M. G. Finn

  DOI：10.1021/jo015632y

  日期：2001.6.1

  The title compound, the condensation product of sulfur dichloride and 1,5-cyclooctadiene, is a reliable acceptor of a wide variety of heteroatom nucleophiles, sometimes in reversible fashion. Optical resolution of the core structure has been achieved and preserved in succeeding transformations. The high reactivity and reliable stereochemical control afforded by this system illustrates the power of neighboring-group participation by the sulfur center.
• Thia-, Aza-, and Selena[3.3.1]bicyclononane Dichlorides: Rates vs Internal Nucleophile in Anchimeric Assistance
  作者：Adrian A. Accurso、So-Hye Cho、Asmarah Amin、Vladimir A. Potapov、Svetlana V. Amosova、M. G. Finn

  DOI：10.1021/jo102440k

  日期：2011.6.3

  Sulfur-, selenium-, and nitrogen-containing compounds bearing leaving groups in the beta-position undergo facile substitution chemistry enabled by anchimeric assistance. Here we provide direct comparisons between such systems in the rigid bicyclo[3.3.1]nonane framework easily derived from 1,5-cyclooctadiene. For a series of dichloride electrophiles of this type, the relative reactivities were found to be Se >> (alkyl)N > S >= (propargyl)N > (phenyl)N, with the reaction rates at the two extremes differing by more than 3 orders of magnitude. For the N-alkyl case, substitution rates were largely independent of the trapping nucleophile but were strongly dependent on solvent, showing that the process is controlled by the formation of the high-energy three-membered cationic intermediate.