(S)-2-[2-(p-tolylsulfinyl)phenyl]acetonitrile | 1286196-72-2

• 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: (S)-2-[2-(p-tolylsulfinyl)phenyl]acetonitrile
• 英文别名: 2-[2-[(S)-(4-methylphenyl)sulfinyl]phenyl]acetonitrile
• CAS: 1286196-72-2
• 化学式: C₁₅H₁₃NOS
• 分子量: 255.34
• InChiKey: BTQRBAIZXDNQEH-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  60.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-[2-(p-tolylsulfinyl)phenyl]acetonitrile 在 18-冠醚-6 、 叔丁基锂 、 sodium hexamethyldisilazane 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 1.01h， 生成 (R)-2-phenyl-2-(prop-2-ynyl)-pent-4-enenitrile
  参考文献：
  名称：

  Asymmetric Intramolecular Pauson–Khand Reaction Mediated by a Remote Sulfenyl or Sulfinyl Group

  摘要：

  In this work, we report the use of the asymmetric intramolecular Pauson-Khand reactions of 4-aryl-4-cyano-1,6-enynes for obtaining enantiomerically enriched bicyclo[3.3.0]octenones, and the influence of both the quaternary stereocenter and the sulfur functions located at ortho-position of the aryl group, on their stereoselectivity and reactivity. The sulfenyl derivatives bearing substituted or unsubstituted triple bonds and mono- and disubstituted alkene moieties afford bicyclo[3,3,0]octenones in high yields with complete diastereocontrol. These results are explained by assuming the association of the lone electron pair at sulfur to the Co-alkyne complexes.

  DOI：

  10.1021/jo3011039

文献信息

• Asymmetric Synthesis of Benzylic Quaternary Difunctionalized Carbons Mediated by a Remote Sulfinyl Group
  作者：José Luis García Ruano、Esther Torrente、Ana M. Martín-Castro

  DOI：10.1021/jo2004204

  日期：2011.5.6

  Enantiomerically enriched α-aryl α-cyanoacetates and α-aryl α-acylacetonitriles bearing a benzylic quaternary stereocenter have been readily synthesized by stereoselective reaction of 2-alkyl-2-[2-(p-tolylsulfinyl)phenyl]acetonitriles with different acylating and alkoxycarbonylating reagents under basic conditions. The stereoselectivity of the reactions proved closely dependent on the nature of the

  通过2-烷基-2- [2-（对-甲苯基亚磺酰基）苯基]乙腈与不同的酰化和烷氧基羰基化反应的立体选择性反应，可以轻松合成对映体富集的α-芳基α-氰基乙酸酯和α-芳基α-酰基乙腈试剂在基本条件下。事实证明，反应的立体选择性与中间碳负离子种类的性质密切相关，中间碳负离子种类的演化受到亚磺酰基作为远程手性助剂的有效控制。