(E)-4-methyl-N-(1-methylpyrrolidin-2-ylidene)benzenesulfonamide | 131657-46-0

• 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: (E)-4-methyl-N-(1-methylpyrrolidin-2-ylidene)benzenesulfonamide
• 英文别名: 4-Methyl-N-(1-methylpyrrolidin-2-ylidene)benzenesulfonamide；(NE)-4-methyl-N-(1-methylpyrrolidin-2-ylidene)benzenesulfonamide
• CAS: 131657-46-0
• 化学式: C₁₂H₁₆N₂O₂S
• 分子量: 252.337
• InChiKey: YPSHFRBMXMFKSH-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  58.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-4-methyl-N-(1-methylpyrrolidin-2-ylidene)benzenesulfonamide 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 rel-(3S,1'R)-1-methyl-3-(1-hydroxybenzyl)-3-(2-propenyl)-2-(((4-methylphenyl)sulfonyl)imino)pyrrolidine
  参考文献：
  名称：

  Reactions and diastereoselectivity of N2-arylsulfonyl amidine anions

  摘要：

  Cyclic N1-alkyl-N2-sulfonyl amidine anions undergo stereoselective aldol reactions to give the syn diastereoisomer as the major product. The ratio of syn to anti aldol products decreases as the size of the N1-alkyl increases. This is interpreted as a change in the transition state from an open-aldol to a closed-Zimmerman-Traxler-type transition state.

  DOI：

  10.1021/jo00004a035
• 作为产物：
  描述：

  对甲苯磺酰氯 在 10-phenyl-9-(2,4,6-trimethylphenyl)acridinium tetrafluoroborate 、 叠氮化四丁基铵 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 11.0h， 生成 (E)-4-methyl-N-(1-methylpyrrolidin-2-ylidene)benzenesulfonamide
  参考文献：
  名称：

  叔胺与磺酰叠氮化物的光诱导级联反应：Synthesis衍生物的合成

  摘要：

  蓝光下a啶盐促进的叔胺与磺酰叠氮化物的无金属级联反应得到了开发，并以中等至良好的收率提供了derivatives衍生物。a胺盐通过via啶盐促进的单电子转移从叔胺生成烯胺，随后通过磺酰叠氮化物和CH 2 N 2的释放[3 + 2]环化获得所需的产物。

  DOI：

  10.1002/adsc.201900359

文献信息

• Direct electrochemical imidation of aliphatic amines<i>via</i> anodic oxidation
  作者：Li Zhang、Ji-Hu Su、Sujing Wang、Changfeng Wan、Zhenggen Zha、Jiangfeng Du、Zhiyong Wang

  DOI：10.1039/c1cc10871a

  日期：——

  Direct electrochemical synthesis of sulfonyl amidines from aliphatic amines and sulfonyl azides was realized with good to excellent yields.

  直接电化学合成烷基胺和磺酰叠氮化合物，产率良好至优异。
• Synthesis of N -Sulfonylformamidines by tert -butyl Hydroperoxide–Promoted, metal-free, direct oxidative dehydrogenation of aliphatic amines
  作者：Ayijiamali Rouzi、Ruzeahong Hudabaierdi、Abudureheman Wusiman

  DOI：10.1016/j.tet.2018.03.074

  日期：2018.5

  A direct and convenient metal-free method to prepare sulfonyl amidines in the presence of aqueous tert-butyl hydroperoxide (T-HYDRO) has been developed. Different tertiary and secondary amines were tested for compatibility with the oxidative conditions and could be coupled with sulfonyl azides to form the corresponding amidines in moderate to good yields.

  已经开发了在水性叔丁基过氧化氢（T-HYDRO）存在下制备磺酰基am的直接且方便的无金属方法。测试了不同的叔胺和仲胺与氧化条件的相容性，并且可以将其与磺酰叠氮化物偶联以中等至良好的产率形成相应的am。
• Visible-Light-Mediated Sulfonylimination of Tertiary Amines with Sulfonylazides Involving C_sp³–C_sp³ Bond Cleavage
  作者：Jiao Gui、Haisheng Xie、Huanfeng Jiang、Wei Zeng

  DOI：10.1021/acs.orglett.9b00786

  日期：2019.4.19

  Visible-light-induced cross-coupling of arylsulfonyl azides with tertiaryamines in the presence of Eosin Y at room temperature has been achieved. This transformation features alkyl C–C bond cleavage and provides a green approach to N-sulfonylamidines under mild conditions.

  在室温下，在曙红Y存在下，已经实现了可见光诱导的芳基磺酰叠氮化物与叔胺的交叉偶联。这种转化具有烷基C–C键断裂的特性，并在温和条件下为N-磺酰lam提供了绿色的方法。
• Synthesis of Cyclic Amidines by Iridium-Catalyzed Deoxygenative Reduction of Lactams and Tandem Reaction with Sulfonyl Azides
  作者：Youliang He、Xiaoming Wang

  DOI：10.1021/acs.orglett.0c03953

  日期：2021.1.1

  An efficient and convenient synthesis of various cyclic amidines has been achieved via iridium-catalyzed deoxygenative reduction of lactams with a silane followed by a one-pot cycloaddition reaction with sulfonyl azides. Using the novel tandem procedure, a large array of cyclic amidines bearing various sized rings were synthesized in good yields from readily available lactams. This methodology has

  通过用硅烷催化的内酰胺的铱催化的内酰胺脱氧还原，然后与磺酰叠氮化物的一锅环加成反应，已经实现了各种环状am的高效便捷合成。使用新颖的串联程序，从容易获得的内酰胺以高收率合成了各种带有各种大小环的环状am。该方法已成功用于带有内酰胺部分的复杂结构的后期多样化。
• Interception of amide ylides with sulfonamides: synthesis of (<i>E</i>)-<i>N</i>-sulfonyl amidines catalyzed by Zn(OTf)₂
  作者：Jijun Chen、Wenhao Long、Shangwen Fang、Yonggang Yang、Xiaobing Wan

  DOI：10.1039/c7cc07364j

  日期：——

  Through the interception of amide ylides with sulfonamides, we herein report the first general example of an intermolecular condensation reaction between sulfonamides and amides. Beyond formamides, this approach was successfully applied to a variety of lactams and linear amides, giving rise to a broad array of (E)-N-sulfonyl amidines.

  通过用磺酰胺截留酰胺基化物，我们在此报道了磺酰胺和酰胺之间的分子间缩合反应的第一个一般实例。除甲酰胺外，该方法已成功应用于各种内酰胺和线性酰胺，从而产生了多种（E）-N-磺酰基am。