1-[2-(4-甲基苯基)磺酰基乙基]吡咯烷 | 16191-66-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-[2-(4-甲基苯基)磺酰基乙基]吡咯烷
• 英文名称: 1-[2-(toluene-4-sulfonyl)-ethyl]-pyrrolidine
• 英文别名: 1-[2-(4-Methylphenyl)sulfonylethyl]pyrrolidine
• CAS: 16191-66-5
• 化学式: C₁₃H₁₉NO₂S
• 分子量: 253.365
• InChiKey: WIHMTJNZZPFMGZ-UHFFFAOYSA-N

物化性质

• 熔点：
  65.5-66.0 °C(Solv: hexane (110-54-3))
• 沸点：
  418.6±45.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[2-(4-甲基苯基)磺酰基乙基]吡咯烷 在 六甲基磷酰三胺 、 正丁基锂 、 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.5h， 生成 (1-butyl-vinyl)-p-tolyl sulfone
  参考文献：
  名称：

  一种制备 α-烷基化乙烯基砜及其转化为烯丙基砜的简便方法

  摘要：

  2-吡咯烷烷基对甲苯基砜很容易通过将吡咯烷加成到乙烯基或烯丙基砜中而获得，通过 α-烷基化随后消除吡咯烷基，转化为相应的 α-烷基化乙烯基砜。一些α-烷基化乙烯基砜进一步转化为相应的烯丙基砜。

  DOI：

  10.1246/cl.1986.341
• 作为产物：
  描述：

  1-phenylseleno-2-(p-toluenesulfonyl)ethyne 在 sodium tetrahydroborate 、 nickel dichloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 8.25h， 生成 1-[2-(4-甲基苯基)磺酰基乙基]吡咯烷
  参考文献：
  名称：

  Additions of Organocopper Reagents and Heteroatom Nucleophiles to 1-Phenylseleno-2-(p-toluenesulfonyl)ethyne. Preparation of Vinyl and Allenic Sulfones and Formation of Michael, Anti-Michael, and Rearrangement Products

  摘要：

  1-Phenylseleno-2-(p-toluenesulfonyl)ethyne (4) was produced nearly quantitatively from p-(toluenesulfonyl)ethyne and benzeneselenenyl chloride. It underwent stereo- and regioselective syn-additions of organocopper reagents RCu(CN)Li to the beta-position of the sulfone moiety to afford adducts 5. Further reaction of the products with reagents RCu(SePh)Li resulted in substitution of the phenylseleno group with retention of configuration. Control of E,Z-stereochemistry in the product beta,beta-disubstituted vinyl sulfones is therefore achieved by the order of addition of the reagents. Selenoxide syn-elimination of adducts 5 afforded the corresponding allenic sulfones. The additions of amines and alkoxides to 4 produced the corresponding anti-Michael regioisomers (where attack occurred a to the sulfone group) as the major or sole products. The additions were highly stereoselective, proceeding by anti-addition in the anti-Michael series and by syn-addition in the corresponding Michael regioisomers. The reactions of 4 with thiolates and selenolates were more complex, affording rearranged adducts and Michael adducts as the major and minor products, respectively. The formation of the rearranged products can be rationalized by a series of addition-elimination processes. Phenylselenoethyne (43) underwent conjugate additions of pyrrolidine, sodium methoxide, sodium ethanethiolate, and benzeneselenolate anion, affording the corresponding cis isomers via anti-addition. The experiments with heteroatom nucleophiles and acetylenes 4 and 43 show that the phenylseleno group has a surprisingly large activating effect upon conjugate additions.

  DOI：

  10.1021/jo981224r

文献信息

• INOMATA, KATSUHIKO;TANAKA, YUHJI;SASAOKA, SHIN-ICHI;KINOSHITA, HIDEKI;KOT+, CHEM. LETT., 1986, N 3, 341-344
  作者：INOMATA, KATSUHIKO、TANAKA, YUHJI、SASAOKA, SHIN-ICHI、KINOSHITA, HIDEKI、KOT+

  DOI：——

  日期：——
• Additions of Organocopper Reagents and Heteroatom Nucleophiles to 1-Phenylseleno-2-(<i>p</i>-toluenesulfonyl)ethyne. Preparation of Vinyl and Allenic Sulfones and Formation of Michael, Anti-Michael, and Rearrangement Products
  作者：Thomas G. Back、Richard J. Bethell、Masood Parvez、Daniel Wehrli

  DOI：10.1021/jo981224r

  日期：1998.10.1

  1-Phenylseleno-2-(p-toluenesulfonyl)ethyne (4) was produced nearly quantitatively from p-(toluenesulfonyl)ethyne and benzeneselenenyl chloride. It underwent stereo- and regioselective syn-additions of organocopper reagents RCu(CN)Li to the beta-position of the sulfone moiety to afford adducts 5. Further reaction of the products with reagents RCu(SePh)Li resulted in substitution of the phenylseleno group with retention of configuration. Control of E,Z-stereochemistry in the product beta,beta-disubstituted vinyl sulfones is therefore achieved by the order of addition of the reagents. Selenoxide syn-elimination of adducts 5 afforded the corresponding allenic sulfones. The additions of amines and alkoxides to 4 produced the corresponding anti-Michael regioisomers (where attack occurred a to the sulfone group) as the major or sole products. The additions were highly stereoselective, proceeding by anti-addition in the anti-Michael series and by syn-addition in the corresponding Michael regioisomers. The reactions of 4 with thiolates and selenolates were more complex, affording rearranged adducts and Michael adducts as the major and minor products, respectively. The formation of the rearranged products can be rationalized by a series of addition-elimination processes. Phenylselenoethyne (43) underwent conjugate additions of pyrrolidine, sodium methoxide, sodium ethanethiolate, and benzeneselenolate anion, affording the corresponding cis isomers via anti-addition. The experiments with heteroatom nucleophiles and acetylenes 4 and 43 show that the phenylseleno group has a surprisingly large activating effect upon conjugate additions.
• A CONVENIENT METHOD FOR THE PREPARATION OF α-ALKYLATED VINYLIC SULFONES AND THEIR CONVERSION TO ALLYLIC SULFONES
  作者：Katsuhiko Inomata、Yuhji Tanaka、Shin-ichi Sasaoka、Hideki Kinoshita、Hiroshi Kotake

  DOI：10.1246/cl.1986.341

  日期：1986.3.5

  sulfones, which were readily available by the addition of pyrrolidine to vinylic or allylic sulfones, were converted to the corresponding α-alkylated vinylic sulfones through α-alkylation followed by elimination of pyrrolidino group. Some of the α-alkylated vinylic sulfones were further transformed to the corresponding allylic sulfones.

  2-吡咯烷烷基对甲苯基砜很容易通过将吡咯烷加成到乙烯基或烯丙基砜中而获得，通过 α-烷基化随后消除吡咯烷基，转化为相应的 α-烷基化乙烯基砜。一些α-烷基化乙烯基砜进一步转化为相应的烯丙基砜。