t-butyl N-benzenesulfanyl-N-(1,2-propadienyl)carbamate | 566164-38-3

• 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: t-butyl N-benzenesulfanyl-N-(1,2-propadienyl)carbamate
• CAS: 566164-38-3
• 化学式: C₁₄H₁₇NO₂S
• 分子量: 263.36
• InChiKey: AYLPOVJLGKRWCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  54.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  t-butyl N-benzenesulfanyl-N-(1,2-propadienyl)carbamate 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 20.0h， 以72%的产率得到t-butyl N-benzenesulfanyl-N-(propenyl)carbamate
  参考文献：
  名称：

  Iron(II)-Catalyzed Sulfimidation and [2,3]-Sigmatropic Rearrangement of Propargyl Sulfides with tert-Butoxycarbonyl Azide. Access to N-Allenylsulfenimides

  摘要：

  The iron(II)-catalyzed Bach reaction of tert-butoxycarbonyl azide (BocN(3)) and allyl sulfides has been extended to include propargyl sulfides, which give N-allenylsulfenimide products. Using 10 mol % dppeFeCl(2) as catalyst the reaction proceeds at 0 degreesC with a number of different propargyl sulfides in 31-73% isolated yield. The reaction is limited by product instability toward catalyst and termination of the catalytic cycle by excess BocN3. N-Allenylsulfenimide 2b smoothly undergoes catalytic hydrogenation and a Diels-Alder reaction with cyclopentadiene.

  DOI：

  10.1021/jo0340410
• 作为产物：
  描述：

  thiophenolate 在 [1,2-双(二苯基膦)乙烷]二氯化铁(II) 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 生成 t-butyl N-benzenesulfanyl-N-(1,2-propadienyl)carbamate
  参考文献：
  名称：

  Iron(II)-Catalyzed Sulfimidation and [2,3]-Sigmatropic Rearrangement of Propargyl Sulfides with tert-Butoxycarbonyl Azide. Access to N-Allenylsulfenimides

  摘要：

  The iron(II)-catalyzed Bach reaction of tert-butoxycarbonyl azide (BocN(3)) and allyl sulfides has been extended to include propargyl sulfides, which give N-allenylsulfenimide products. Using 10 mol % dppeFeCl(2) as catalyst the reaction proceeds at 0 degreesC with a number of different propargyl sulfides in 31-73% isolated yield. The reaction is limited by product instability toward catalyst and termination of the catalytic cycle by excess BocN3. N-Allenylsulfenimide 2b smoothly undergoes catalytic hydrogenation and a Diels-Alder reaction with cyclopentadiene.

  DOI：

  10.1021/jo0340410

文献信息

• Amination and [2,3]-sigmatropic rearrangement of propargylic sulfides using a ketomalonate-derived oxaziridine: synthesis of N-allenylsulfenimides
  作者：Alan Armstrong、Richard S. Cooke、Stephen E. Shanahan

  DOI：10.1039/b307722e

  日期：——

  Amination of propargylic sulfides with a ketomalonate-derived oxaziridine under metal free conditions gives N-Boc-N-allenylsulfenimides via [2,3]-sigmatropic rearrangement.

  在没有金属的条件下，用酮缩酮酸衍生的恶唑烷胺化炔丙基硫化物，通过[2,3]-σ重排得到N-Boc-N-烯丙基亚磺酰亚胺。
• Iron(II)-Catalyzed Sulfimidation and [2,3]-Sigmatropic Rearrangement of Propargyl Sulfides with <i>tert</i>-Butoxycarbonyl Azide. Access to <i>N</i>-Allenylsulfenimides
  作者：James P. Bacci、Kevin L. Greenman、David L. Van Vranken

  DOI：10.1021/jo0340410

  日期：2003.6.1

  The iron(II)-catalyzed Bach reaction of tert-butoxycarbonyl azide (BocN(3)) and allyl sulfides has been extended to include propargyl sulfides, which give N-allenylsulfenimide products. Using 10 mol % dppeFeCl(2) as catalyst the reaction proceeds at 0 degreesC with a number of different propargyl sulfides in 31-73% isolated yield. The reaction is limited by product instability toward catalyst and termination of the catalytic cycle by excess BocN3. N-Allenylsulfenimide 2b smoothly undergoes catalytic hydrogenation and a Diels-Alder reaction with cyclopentadiene.