4-tert-butyl-N-tosylbenzamide | 105536-26-3

• 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: 4-tert-butyl-N-tosylbenzamide
• 英文别名: 4-(1,1-Dimethylethyl)-N-[(4-methylphenyl)sulfonyl]benzamide；4-tert-butyl-N-(4-methylphenyl)sulfonylbenzamide
• CAS: 105536-26-3
• 化学式: C₁₈H₂₁NO₃S
• 分子量: 331.436
• InChiKey: XDOGSLXSHAMLGK-UHFFFAOYSA-N

物化性质

• 密度：
  1.173±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 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：
  71.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-tert-butyl-N-tosylbenzamide 在 四丁基醋酸铵 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 4.0h， 以73%的产率得到3-(4-(tert-butyl)phenyl)-7-methylbenzo[e][1,4,3]oxathiazine 1,1-dioxide
  参考文献：
  名称：

  N-酰基磺酰胺的电化学迁移环化

  摘要：

  N-酰基磺酰胺的电化学迁移环化已被开发用于轻松制备各种具有生物学意义但合成具有挑战性的苯并噻嗪二氧化物。

  DOI：

  10.1002/anie.202206058
• 作为产物：
  描述：

  对叔丁基苯甲醛 、 [(N-tosylimino)iodo]benzene 在 吡啶 、 iron(II) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以95%的产率得到4-tert-butyl-N-tosylbenzamide
  参考文献：
  名称：

  Iron(II)-Catalyzed Amidation of Aldehydes with Iminoiodinanes at Room Temperature and under Microwave-Assisted Conditions

  摘要：

  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.

  DOI：

  10.1021/jo200284a

文献信息

• Palladium-Catalyzed [4+2] Annulation of Aryl and Alkenyl Carboxamides with 1,3-Dienes via C–H Functionalization: Synthesis of 3,4-Dihydroisoquinolones and 5,6-Dihydropyridinones
  作者：Manman Sun、Jinshan Li、Weida Chen、Haijian Wu、Jianguo Yang、Zhiming Wang

  DOI：10.1055/s-0039-1690219

  日期：2020.4

  Palladium-catalyzed [4+2] annulation of aryl and alkenyl carboxamides with 1,3-dienes via C–H functionalization is developed using air as the terminal oxidant. The method demonstrates good functional group tolerance and high stereoselectivity, affording a series of 3,4-dihydroisoquinolones and 5,6-dihydropyridinones in yields of up to 99%. Palladium-catalyzed [4+2] annulation of aryl and alkenyl carboxamides

  抽象的 使用空气作为末端氧化剂，开发了钯通过C–H功能化与1，3-二烯催化的[4 + 2]芳基和烯基羧酰胺环化反应。该方法显示出良好的官能团耐受性和高立体选择性，提供了一系列3,4-二氢异喹诺酮和5,6-二氢吡啶酮，收率高达99％。 使用空气作为末端氧化剂，开发了钯通过C–H功能化与1，3-二烯催化的[4 + 2]芳基和烯基羧酰胺环化反应。该方法显示出良好的官能团耐受性和高立体选择性，提供了一系列3,4-二氢异喹诺酮和5,6-二氢吡啶酮，收率高达99％。
• Redox-Neutral Rhodium-Catalyzed [4+1] Annulation through Formal Dehydrogenative Vinylidene Insertion
  作者：Huan Liu、Shengjin Song、Cheng-Qiang Wang、Chao Feng、Teck-Peng Loh

  DOI：10.1002/cssc.201601341

  日期：2017.1.10

  A synthetic protocol for the expedient construction of 5‐methylene‐1H‐pyrrol‐2(5H)‐one derivatives through rhodium‐catalyzed [4+1] annulation with gem‐difluoroacrylate as the C1 component was reported. By taking advantage of the twofold C−F bond cleavage occurring during the annulation, this reaction not only allows the synthesis of these heterocyclic compounds under overall oxidant‐free conditions

  据报道，通过铑催化的[4 + 1]环化，使用宝石二氟丙烯酸酯作为C 1组分，可方便地构建5-亚甲基-1 H-吡咯-2（5 H）-one衍生物的合成方案。通过利用在成环过程中发生的两倍CF键断裂，该反应不仅可以使这些杂环化合物在完全无氧化剂的条件下合成，而且还可以实现立体定向转化。所采用的非常温和的反应条件可确保与多种合成上有用的官能团兼容。
• Selective Gram-Scale C–H Carbenoid Functionalization of <i>N</i>-Sulfonylarylamides with a Rhodium Catalyst
  作者：Yi Dong、Bo Mei、Xue-Peng Zhang、Heng Xu

  DOI：10.1021/acs.joc.1c01182

  日期：2021.9.3
• US8034851B1
  申请人：——

  公开号：US8034851B1

  公开（公告）日：2011-10-11
• 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.