N-(4-(tert-butyl)benzylidene)-4-methylbenzenesulfonamide | 691370-35-1

• 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-(4-(tert-butyl)benzylidene)-4-methylbenzenesulfonamide
• 英文别名: N-[(4-tert-butylphenyl)methylidene]-4-methylbenzenesulfonamide
• CAS: 691370-35-1
• 化学式: C₁₈H₂₁NO₂S
• 分子量: 315.436
• InChiKey: HHJDNCIVRQPSHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  54.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-(tert-butyl)benzylidene)-4-methylbenzenesulfonamide 在 1-(2,2-dimethylpropyl)-3-[(S)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methyl]thiourea 、 间氯过氧苯甲酸 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 24.0h， 以93%的产率得到(S)-3-(4-tert-butylphenyl)-2-tosyloxaziridine
  参考文献：
  名称：

  Novel chiral thiourea organocatalysts for the catalytic asymmetric oxaziridination

  摘要：

  Catalytic enantioselective oxaziridination is one of the challenging reactions in the oxidation of organic molecules. In this article, a series of novel chiral thiourea moleculars were synthesized from natural cinchona alkaloids and primary amines. By using these molecules as organocatalysts and m-chloroper-oxybenzoicacid (m-CPBA) as the oxidant, a methodology on highly enantioselective epoxidation of al-dimines has been developed. Several optically active oxaziridines have been constructed in good yields (up to 95%) and moderate to excellent enantioselectivities (up to 99% ee). A plausible transition state was also proposed. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.12.010
• 作为产物：
  描述：

  对叔丁基苯甲醛 、 对甲苯磺酰胺 在 四氯化钛 、 三乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 以52%的产率得到N-(4-(tert-butyl)benzylidene)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Enantioselective Friedel–Crafts reactions between phenols and N-tosylaldimines catalyzed by a leucine-derived bifunctional catalyst

  摘要：

  利用L-亮氨酸作为原料制备的二功能催化剂，开发了苯酚与N-对甲苯磺酰亚胺之间的对映选择性Friedel-Crafts反应。获得了高产率（最高达96%）和良好至高对映体过量（最高达95% ee）的手性苄胺产物。

  DOI：

  10.1039/c2cc31735d

文献信息

• Branched Amine Synthesis via Aziridine or Azetidine Opening with Organotrifluoroborates by Cooperative Brønsted/Lewis Acid Catalysis: An Acid-Dependent Divergent Mechanism
  作者：Truong N. Nguyen、Jeremy A. May

  DOI：10.1021/acs.orglett.8b01394

  日期：2018.6.15

  A practical catalytic method to synthesize β,β- and γ,γ-substituted amines by opening aziridines and azetidines, respectively, using alkenyl, alkynyl, or aryl/heteroaryl trifluoroborate salts is described. This reaction features simple open-flask reaction conditions, the use of transition-metal-free catalysis, complete regioselectivity, and high diastereoselectivity. Preliminary mechanistic studies

  描述了一种实用的催化方法，该方法通过使用烯基，炔基或芳基/杂芳基三氟硼酸盐分别打开氮丙啶和氮杂环丁烷来合成β，β-和γ，γ-取代的胺。该反应具有简单的开瓶反应条件，使用无过渡金属的催化，完全的区域选择性和高的非对映选择性。初步的机理研究表明，碳正离子形成是不利的。存在布朗斯台德酸时，有利于立体定向添加，而在不存在立体异构时，则有利于立体转化，这表明存在不同的机理。
• Chiral‐Directing‐Group‐Assisted Rhodium(III)‐Catalyzed Asymmetric Addition of Inert Arene C−H Bond to Aldimines with Subsequent Intramolecular Cyclization
  作者：Xuhong Cai、Wenkun Chen、Ruifang Nie、Jun Wang

  DOI：10.1002/chem.202103319

  日期：2021.12

  An asymmetric rhodium(III)-catalyzed C−H bond addition to aldimines followed by subsequent intramolecular cyclization to form chiral isoindolinones has been achieved by using a chiral directing group. Various substituted benzamides and aldimines have been smoothly transformed to the corresponding products in up to 68 % yield with up to 93 % ee.

  通过使用手性导向基团，不对称铑 (III) 催化的 C-H 键加成到醛亚胺，随后分子内环化形成手性异吲哚啉酮。各种取代的苯甲酰胺和醛亚胺已顺利转化为相应的产品，产率高达 68%，ee 高达 93%。
• Nickel(0)-Catalyzed Hydroalkenylation of Imines with Styrene and Its Derivatives
  作者：Li-Jun Xiao、Chao-Yue Zhao、Lei Cheng、Bo-Ya Feng、Wei-Min Feng、Jian-Hua Xie、Xiu-Fang Xu、Qi-Lin Zhou

  DOI：10.1002/anie.201713333

  日期：2018.3.19

  A nickel(0)‐catalyzed hydroalkenylation of imines with styrene and its derivatives is described. A wide range of aromatic and aliphatic imines directly coupled with styrene and its derivatives, thus providing various synthetically useful allylic amines with up to 95 % yield. The reaction offers a new atom‐ and step‐economical approach to allylic amines by using alkenes instead of alkenyl‐metallic reagents

  本文介绍了镍（0）催化亚胺与苯乙烯及其衍生物的加氢烯基化反应。各种芳族和脂族亚胺直接与苯乙烯及其衍生物偶联，因此可提供高达95％的收率的各种合成有用的烯丙基胺。通过使用烯烃代替烯基金属试剂，该反应为烯丙基胺提供了一种新的原子经济和分步经济的方法。实验和DFT计算表明，TsNH 2促进了质子从配位烯烃向亚胺的转移，同时形成了新的CC键。
• Ruthenium(II)-Catalyzed CH Bond Activation: An Efficient Route toward Indenamines
  作者：Chen-Hsun Hung、Parthasarathy Gandeepan、Chien-Hong Cheng

  DOI：10.1002/cctc.201402393

  日期：2014.9

  N‐tosylarylimines and alkynes via ruthenium(II)‐catalyzed CH bond activation and annulation is described. The catalytic reaction proceeds well with a broad substrate scope and in good yields. A possible mechanism is proposed that involves imine nitrogen chelation‐assisted ortho‐CH bond activation of the substrate, alkyne insertion, and intramolecular insertion of the CN Ts group into the CRu bond. Isotope‐labeling

  一种由取代indenamines的合成的有效和原子的经济的方法Ñ -tosylarylimines和炔烃经由钌（II） -催化Ç 描述H键活化和环。催化反应在宽范围的底物范围内以良好的产率进行得很好。一种可能的机制提出了涉及亚胺氮螯合辅助邻-C 基板，炔插入，以及TSCN组的分子内插入的C H键活化茹键。进行同位素标记实验以了解反应的潜在机理。
• Pd/Al₂O₃-catalysed redox isomerisation of allyl alcohol: application in aldol condensation and oxidative heterocyclization reactions
  作者：Dániel Zsolnai、Péter Mayer、Kornél Szőri、Gábor London

  DOI：10.1039/c5cy01722j

  日期：——

  The application of the Pd/Al2O3 catalyst in allyl alcohol isomerization and subsequent aldol condensation and heterocyclization reactions is described. The activity of Pd/Al2O3 in these transformations is suggested to be due to the participation of the Lewis acidic sites of the support in the activation of the alcohol towards oxidative dehydrogenation by the metal and subsequent hydride transfer. The

  描述了Pd / Al 2 O 3催化剂在烯丙醇异构化以及随后的醛醇缩合和杂环化反应中的应用。Pd / Al 2 O 3的活性这些转化的推测是由于载体的路易斯酸性位点参与了醇向金属的氧化脱氢和随后的氢化物转移的活化。所得的烯醇（酸酯）/醛可能会因载体的酸碱性质而进一步发生反应。在异构化产物的醛醇缩合反应中，贫电子的芳族醛和杂芳族醛显示出最高的活性，而带有给电子取代基的芳族醛在转化为相应的N-甲苯磺酰基亚胺后反应。1,2-二取代的芳族化合物在一锅多步反应序列中得到杂环产物。