N-(烯丙基氨基甲酰基)-4-甲基苯磺酰胺 | 51506-31-1

• 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: N-(烯丙基氨基甲酰基)-4-甲基苯磺酰胺
• 英文名称: N-tosyl-N'-allylurea
• 英文别名: N-p-Toluolsulfonyl-N'-allyl-harnstoff；N-(allylcarbamoyl)-4-methylbenzenesulfonamide；N-allyl-N'-(toluene-4-sulfonyl)-urea；N-Allyl-N'-(toluol-4-sulfonyl)-harnstoff；1-({[(Allylamino)carbonyl]amino}sulfonyl)-4-methylbenzene；1-(4-methylphenyl)sulfonyl-3-prop-2-enylurea
• CAS: 51506-31-1
• 化学式: C₁₁H₁₄N₂O₃S
• 分子量: 254.31
• InChiKey: JKSLHSQGBONPCN-UHFFFAOYSA-N

物化性质

• 熔点：
  141-143 °C
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  83.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(烯丙基氨基甲酰基)-4-甲基苯磺酰胺 生成 1-丙基-3-(对甲苯基磺酰基)脲
  参考文献：
  名称：

  Onisi, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1959, vol. 79, p. 559,564

  摘要：

  DOI：
• 作为产物：
  描述：

  1-allyl-3-tosylthiourea 在 sodium hydroxide 、 双氧水 作用下， 生成 N-(烯丙基氨基甲酰基)-4-甲基苯磺酰胺
  参考文献：
  名称：

  Onisi, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1959, vol. 79, p. 559,564

  摘要：

  DOI：

文献信息

• A Palladium-Catalyzed Aminoalkynylation Strategy towards Bicyclic Heterocycles: Synthesis of (±)-Trachelanthamidine
  作者：Stefano Nicolai、Cyril Piemontesi、Jérôme Waser

  DOI：10.1002/anie.201100718

  日期：2011.5.9

  Sweet cyclizations: The synthesis of pyrrolizidines and indolizidines has been achieved. Olefins were subjected to an intramolecular palladium‐catalyzed aminoalkynylation with the hypervalent iodine reagent TIPS‐EBX. After removal of the protecting group, a two‐step cyclization sequence and subsequent reduction led to the natural product (±)‐trachelanthamidine (see scheme; TIPS‐EBX=triisopropylsilyl

  甜蜜的环化反应：吡咯嗪和吲哚并嗪的合成已经完成。烯烃用高价碘试剂TIPS-EBX进行了分子内钯催化的氨基炔基化反应。除去保护基团后，分两步环化，随后还原，得到天然产物（±）-曲安啶（参见方案； TIPS-EBX =三异丙基甲硅烷基乙炔基苯并恶唑啉酮）。
• N-Heterocyclic carbene–gold(I)-catalyzed carboheterofunctionalization of alkenes with arylboronic acids
  作者：Shifa Zhu、Lijuan Ye、Wanqing Wu、Huanfeng Jiang

  DOI：10.1016/j.tet.2013.09.097

  日期：2013.12

  A new approach to the synthesis of pyrrolidine, tetrahydrofuran, and imidazolidin-2-one via N-heterocyclic carbene–gold(I)-catalyzed intramolecular amino- or oxyarylation reactions from a wide variety of alkene substrates such as N-allyl amides, alcohols, carboxylic acids, and ureas in the presence of Selectfluor under mild conditions has been developed.

  通过一种新方法吡咯烷，四氢呋喃，和咪唑烷-2-酮的合成Ñ -杂环卡宾-金（I）催化的分子内的氨基或oxyarylation从各种各样的烯烃底物如反应的ñ -烯丙基酰胺，醇已经开发出在温和条件下在Selectfluor的存在下制备羧酸，羧酸和脲的方法。
• Copper-catalyzed regioselective 1,2-thioamidation of alkenes
  作者：Dengke Li、Tingting Mao、Jinbo Huang、Qiang Zhu

  DOI：10.1039/c7cc00083a

  日期：——

  .An efficient method for regioselective 1,2-thioamidation of terminal alkenes, catalyzed by copper in the presence of NFSI and thiols, has been disclosed. Under the reaction conditions, amido radical was formed...

  已经公开了在NFSI和硫醇的存在下由铜催化的末端烯烃的区域选择性1，2-硫酰胺化的有效方法。在反应条件下，形成酰胺基。
• Regio-controlled iodoaminocyclization reaction of an ambident nucleophile mediated by LiAl(Ot-Bu)4
  作者：Osamu Kitagawa、Masao Fujita、Hua Li、Takeo Taguchi

  DOI：10.1016/s0040-4039(96)02405-7

  日期：1997.1

  A new and general method of iodine-mediated cyclization reactions of unsaturated carbamates, ureas and amides which gives N-cyclized products as a single regio-isomer was achieved. The present reaction proceeds in good yield through regio-control of an ambident nucleophile by LiAl(Ot-Bu)4, and the regio-control (N-attack vs O-attack) was also found to be remarkably affected by the additive employed

  实现了一种新的，通用的碘介导的不饱和氨基甲酸酯，脲和酰胺环化反应的新方法，该方法可将N环化产物作为一个单一的区域异构体。通过LiAl（O t- Bu）4对环境亲核试剂的区域控制，本反应以良好的收率进行，并且还发现区域控制（N-攻击对O-攻击）受到所用添加剂的显着影响。 。
• Lewis Base-Catalyzed Reaction of Aziridinofullerene with Ureas for the Preparation of Fulleroimidazolidinones
  作者：Meng-Lei Xing、Xin-Wei Lu、Chun-Bao Miao、Jia-Xing Li、Xiao-Qiang Sun、Hai-Tao Yang

  DOI：10.1021/jo5022772

  日期：2014.12.5

  The Lewis base-catalyzed double nucleophilic substitution reaction of N-tosylaziridinofullerene with various ureas allows the easy preparation of fulleroimidazolidinones with a high tolerance for functional groups. Alkyl-substituted ureas show better reactivity than aryl-substituted ureas.