1-allyl-2-(4-methylphenylsulfonyl)acetamide | 196393-43-8

• 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: 1-allyl-2-(4-methylphenylsulfonyl)acetamide
• 英文别名: N-allyl-2-(4-methylphenylsulfonyl)acetamide；N-allyl-2-(toluene-4-sulfonyl)acetamide；Acetamide, 2-[(4-methylphenyl)sulfonyl]-N-2-propenyl-；2-(4-methylphenyl)sulfonyl-N-prop-2-enylacetamide
• CAS: 196393-43-8
• 化学式: C₁₂H₁₅NO₃S
• 分子量: 253.322
• InChiKey: GPOOOQNVBJTVLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-allyl-2-(4-methylphenylsulfonyl)acetamide 在 palladium on activated charcoal 、 Grubbs catalyst first generation lithium aluminium tetrahydride 、 三氟化硼乙醚 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 40.0h， 生成 1-Methoxy-3-(toluene-4-sulfonyl)-octahydro-quinolizin-4-one
  参考文献：
  名称：

  A versatile approach to 6-substituted-5-methoxy-δ-lactam framework and application to the formal synthesis of (±)-homopumiliotoxin 223G

  摘要：

  Of the various 6-substituted-5-methoxy-delta-lactams 6 were synthesized from alpha-sulfonyl acetamide 9 in 4 steps in good yield. The key glutarimides 7 were obtained via facile [3+3] annulation. The method featured regioselective introduction of C-6 substituents in glutarimides 7. Synthesis of tribenzyl lactam 8 and the formal synthesis of (+/-)-homopumiliotoxin 223G were also reported. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.001
• 作为产物：
  描述：

  N-(氯乙酰基)烯丙胺 、 sodium 4-methylbenzenesulfinate 以 1,4-二氧六环 、 水 为溶剂， 反应 15.0h， 以2.15 g的产率得到1-allyl-2-(4-methylphenylsulfonyl)acetamide
  参考文献：
  名称：

  通过形式上的[3 + 2]环化和闭环复分解合成伪三碘烷

  摘要：

  碱诱导的α-磺酰基乙酰胺与（Z）-2-溴丙烯酸酯的逐步偶联/环化[3 + 2]环化反应，可在一锅合成中得到具有三个连续手性中心且具有反式-反式取向的多取代焦谷氨酸酯。通过闭环复分解（RCM）方法获得吡咯嗪核骨架。这种简便的策略被用来合成伪三碘烷。

  DOI：

  10.1016/j.tet.2004.04.074

文献信息

• Synthesis of fused bicyclic glutarimides
  作者：Meng-Yang Chang、Chung-Yi Chen、Shui-Tein Chen、Nein-Chen Chang

  DOI：10.1016/s0040-4020(03)01198-0

  日期：2003.9

  We describe an efficient route towards the synthesis of fused bicyclic glutarimides using facile [3+3] reaction of α-sulfonylacetamides with different α,β-unsaturated esters as the key step. Intramolecular cyclization of 4-substituted 3-sulfonylglutarimide to form 5,6-, 6,6- or 6,7-fused bicyclic glutarimides was accomplished via alkylation, oxidative cyclization or ring-closing metathesis in modest

  我们描述了使用α-磺酰基乙酰胺与不同的α，β-不饱和酯的简便[3 + 3]反应作为合成稠合双环戊二酰亚胺的有效途径的关键步骤。通过烷基化，氧化环化或闭环复分解以适度的产率完成4-取代的3-磺酰基戊二酰亚胺的分子内环化以形成5,6-，6,6-或6,7-稠合的双环戊二酰亚胺。
• Cycloadditions between methyl (Z)-2-bromo-4,4,4-trifluoro-2-butenoate and various tosylacetamides: Synthesis of trifluoromethylated pyroglutamates and 2-pyridones derivatives
  作者：Hong-Hai Zhang、Wei Shen、Long Lu

  DOI：10.1016/j.tetlet.2018.01.095

  日期：2018.3

  Cycloaddition reactions between methyl (Z)-2-bromo-4,4,4-trifluoro-2-butenoate and various 2-tosylacetamides are described. Various 2-tosylacetamides react with methyl (Z)-2-bromo-4,4,4-trifluoro-2-butenoate in the presence of NaH at room temperature in one step to form trifluoromethylated pyroglutamates as single diastereomers. However, employing the same reactants using t-BuOK as base at −78 °C results

  描述了（Z）-2-溴-4,4,4-三氟-2-丁烯酸甲酯与各种2-甲苯磺酰基乙酰胺之间的环加成反应。在室温下，在NaH存在下，各种2-甲苯基乙酰胺与（Z）-2-溴-4,4,4-三氟-2-丁烯酸甲酯在室温下反应，以形成单一非对映异构体的三氟甲基化焦谷氨酸酯。然而，在-78℃下使用以t- BuOK为碱的相同反应物导致三氟甲基化2-吡啶酮的形成。提出了反应的闭环机理。
• One-pot facile conversion of Baylis–Hillman adduct into N-alkyl 3-(E)-alkylidene-5-substituted sulfonylpiperidine-2,6-dione. Formal synthesis of tacamonine
  作者：Chung-Yi Chen、Meng-Yang Chang、Ru-Ting Hsu、Shui-Tein Chen、Nein-Chen Chang

  DOI：10.1016/j.tetlet.2003.08.053

  日期：2003.11

  stepwise [3+3] strategy to N-alkyl 3-(E)-alkylidene-5-substituted sulfonylpiperidine-2,6-dione 1 used various N-alkyl α-substituted sulfonylacetamides 2 and α,β-unsaturated esters 3 as starting materials. α,β-Unsaturated esters 3 were generated by Baylis–Hillman reaction. A ring closure mechanism was proposed for the reactions. This method provides a convenient formal synthesis of tacamonine.

  N-烷基3-（E）-亚烷基-5-取代的磺酰基哌啶-2,6-二酮1的逐步[3 + 3]策略使用各种N-烷基α-取代的磺酰基乙酰胺2和α，β-不饱和酯3作为起始材料。α，β-不饱和酯3是通过Baylis-Hillman反应生成的。提出了反应的闭环机理。该方法提供了塔卡莫宁的方便的形式合成。
• Chang, Meng-Yang; Chen, Shui-Tein; Chang, Nein-Chen, Heterocycles, 2002, vol. 57, # 12, p. 2321 - 2334
  作者：Chang, Meng-Yang、Chen, Shui-Tein、Chang, Nein-Chen

  DOI：——

  日期：——
• Regioselective Reduction of 3-Sulfonyl Glutarimides to 3,4-Dihydro-5-sulfonylpyridin-2-ones. Formal Synthesis of the Indolizidine 8a-<i>e</i><i>pi</i>-Dendroprimine
  作者：Ru-Ting Hsu、Li-Ming Cheng、Nein-Chen Chang、Huo-Mu Tai

  DOI：10.1021/jo025539p

  日期：2002.7.1

  Sodium borohydride regioselectively reduced various 3-sulfonyl glutarimides 1 to hydroxy piperidones 2, which were further dehydrated to 3,4-dihydro-5-sulfonylpyridin-2-ones 3 in the presence of boron trifluoride. Formal synthesis of 8a-epi-dendroprimine (4) possessing an indolizidine ring system has been accomplished via intramolecular radical cyclization of cyclic vinyl sulfone 5.