N-tosylcinnamamide | 94299-15-7

• 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: N-tosylcinnamamide
• 英文别名: N-(4-methylphenyl)sulfonyl-3-phenylprop-2-enamide
• CAS: 94299-15-7
• 化学式: C₁₆H₁₅NO₃S
• 分子量: 301.366
• InChiKey: WKPGCKTWPKWOIC-UHFFFAOYSA-N

物化性质

• 熔点：
  136-137 °C
• 密度：
  1.262±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 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-丙烯基苯 、 N-tosylcinnamamide 在 2,6-二甲基吡啶 、 4-甲氧基苯硫酚 、 9-mesityl-10-methylacridinium tetrafluoroborate 作用下， 以 氯仿 为溶剂， 反应 72.0h， 以13%的产率得到
  参考文献：
  名称：

  Amide and Amine Nucleophiles in Polar Radical Crossover Cycloadditions: Synthesis of γ-Lactams and Pyrrolidines

  摘要：

  In this work we present a direct catalytic synthesis of gamma-lactams and pyrrolidines from alkenes and activated unsaturated amides or protected unsaturated amines, respectively. Using a mesityl acridinium single electron photooxidant and a thiophenol cocatalyst under irradiation, we are able to directly forge these important classes of heterocycles with complete regiocontrol.

  DOI：

  10.1021/acs.orglett.5b00316
• 作为产物：
  描述：

  对甲苯磺酰胺 、 肉桂酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以49%的产率得到N-tosylcinnamamide
  参考文献：
  名称：

  Amide and Amine Nucleophiles in Polar Radical Crossover Cycloadditions: Synthesis of γ-Lactams and Pyrrolidines

  摘要：

  In this work we present a direct catalytic synthesis of gamma-lactams and pyrrolidines from alkenes and activated unsaturated amides or protected unsaturated amines, respectively. Using a mesityl acridinium single electron photooxidant and a thiophenol cocatalyst under irradiation, we are able to directly forge these important classes of heterocycles with complete regiocontrol.

  DOI：

  10.1021/acs.orglett.5b00316

文献信息

• Co-Catalyzed Synthesis of <i>N</i>-Sulfonylcarboxamides from Carboxylic Acids and Sulfonyl Azides
  作者：Yue Fang、Zheng-Yang Gu、Shun-Yi Wang、Jin-Ming Yang、Shun-Jun Ji

  DOI：10.1021/acs.joc.8b01300

  日期：2018.8.17

  A Co-catalyzed effective synthesis of N-sulfonylcarboxamides from the reaction of carboxylic acids and organic azides in the presence of isocyanide has been developed. The protocol has the advantages of short time, low temperature, and being oxidant-free, which provides a new and simple approach for the synthesis of N-sulfonylcarboxamides in good to excellent yields with a broad substrate scope.

  已经开发了在异氰酸酯存在下由羧酸和有机叠氮化物的反应共催化有效合成N-磺酰基羧酰胺的方法。该方案具有时间短，温度低，无氧化剂的优点，为合成N-磺酰基甲酰胺提供了一种新的简单方法，具有良好的产率和良好的底物范围。
• Organocatalytic Direct <i>N</i>-Acylation of Amides with Aldehydes under Oxidative Conditions
  作者：Chenguang Zheng、Xiang Liu、Cheng Ma

  DOI：10.1021/acs.joc.7b00457

  日期：2017.7.7

  The direct oxidative N-acylation reaction of primary amides with aryl/α,β-unsaturated aldehydes was achieved in the presence of azolium salt C3 and an inorganic base using 3,3′,5,5′-tetra-tert-butyldiphenoquinone as the oxidant, thus providing an efficient approach for the synthesis of three types of imide compounds including N-sulfonylcarboxamides, N-sulfinylcarboxamides, and dicarboxyimides in good

  直接氧化Ñ伯酰胺与芳基/α，β不饱和醛在氮鎓盐的存在下实现的酰化反应C3和无机碱使用3,3'，5,5'-四-叔-butyldiphenoquinone作为氧化剂，因此为以高收率合成三种类型的酰亚胺化合物（包括N-磺酰基羧酰胺，N-亚磺酰基羧酰胺和二羧酰亚胺）提供了一种有效的方法。
• Iron(II)-Catalyzed Amidation of Aldehydes with Iminoiodinanes at Room Temperature and under Microwave-Assisted Conditions
  作者：Thi My Uyen Ton、Ciputra Tejo、Stefani Tania、Joyce Wei Wei Chang、Philip Wai Hong Chan

  DOI：10.1021/jo200284a

  日期：2011.6.17

  A method for the amidation of aldehydes with PhI=NTs/PhI=NNs as the nitrogen source and an inexpensive iron(II) chloride + pyridine as the in situ formed precatalyst under mild conditions at room temperature or microwave assisted conditions is described. The reaction was operationally straightforward and accomplished in moderate to excellent product yields (20-99%) and with complete chemoselectivity with the new C-N bond forming only at the formylic C-H bond in substrates containing other reactive functional groups. By utilizing microwave irradiation, comparable product yields and short reaction times of 1 h could be accomplished. The mechanism is suggested to involve insertion of a putative iron-nitrene/imido group to the formylic C H bond of the substrate via a H-atom abstraction/radical rebound pathway mediated by the precatalyst [Fe(py)(4)Cl-2] generated in situ from reaction of FeCl2 with pyridine.
• Amide and Amine Nucleophiles in Polar Radical Crossover Cycloadditions: Synthesis of γ-Lactams and Pyrrolidines
  作者：Nathan J. Gesmundo、Jean-Marc M. Grandjean、David A. Nicewicz

  DOI：10.1021/acs.orglett.5b00316

  日期：2015.3.6

  In this work we present a direct catalytic synthesis of gamma-lactams and pyrrolidines from alkenes and activated unsaturated amides or protected unsaturated amines, respectively. Using a mesityl acridinium single electron photooxidant and a thiophenol cocatalyst under irradiation, we are able to directly forge these important classes of heterocycles with complete regiocontrol.