N-(phenylsulfinyl)benzamide | 18513-01-4

• 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-(phenylsulfinyl)benzamide
• 英文别名: N-(benzenesulfinyl)benzamide
• CAS: 18513-01-4
• 化学式: C₁₃H₁₁NO₂S
• 分子量: 245.302
• InChiKey: BWSRMFAAZSDKAA-UHFFFAOYSA-N

物化性质

• 熔点：
  141-143 °C
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(phenylsulfinyl)benzamide 在 盐酸 、 N-氯代丁二酰亚胺 作用下， 以 1,4-二氧六环 、 乙醇 、 乙腈 为溶剂， 反应 45.0h， 生成 4-(phenylsulfonimidoyl)morpholine
  参考文献：
  名称：

  Synthesis and arylation of unprotected sulfonimidamides

  摘要：

  Herein we evaluate different methodologies for the synthesis of unprotected sulfonimidamides. Three different procedures that allow orthogonal deprotection of the imine nitrogen under acidic, nucleophilic, and basic conditions were established. Moreover, we present a highly efficient methodology for functionalization of the imine nitrogen through Pd-catalyzed C-N arylation. RuPhos ligand was shown to allow short reaction time, excellent yields, and allowed coupling of both aryl halides and heteroaryl bromides. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.072
• 作为产物：
  描述：

  苯亚磺酰氯 在 正丁基锂 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.16h， 生成 N-(phenylsulfinyl)benzamide
  参考文献：
  名称：

  Synthesis and arylation of unprotected sulfonimidamides

  摘要：

  Herein we evaluate different methodologies for the synthesis of unprotected sulfonimidamides. Three different procedures that allow orthogonal deprotection of the imine nitrogen under acidic, nucleophilic, and basic conditions were established. Moreover, we present a highly efficient methodology for functionalization of the imine nitrogen through Pd-catalyzed C-N arylation. RuPhos ligand was shown to allow short reaction time, excellent yields, and allowed coupling of both aryl halides and heteroaryl bromides. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.072

文献信息

• 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。
• Synthesis of CF₃-Substituted Sulfoximines from Sulfonimidoyl Fluorides
  作者：Rafal Kowalczyk、Andrew J. F. Edmunds、Roger G. Hall、Carsten Bolm

  DOI：10.1021/ol103030w

  日期：2011.2.18

  N-Protected trifluoromethyl-substituted sulfoximines have been prepared by treatment of sulfonimidoyl fluorides with a combination of the Ruppert−Prakash reagent (TMSCF3) and tetrabutyl ammonium fluoride (TBAF). The starting materials were accessed following two synthetic routes, and for each reaction sequence the substrate scope was evaluated. Accordingly, a wide variety of aryl-substituted products

  通过用Ruppert-Prakash试剂（TMSCF 3）和四丁基氟化铵（TBAF）的组合处理磺酰亚胺基酰氟，可以制得受N保护的三氟甲基取代的亚磺酰亚胺。遵循两种合成路线获取起始原料，并针对每个反应顺序评估底物范围。因此，以中等至良好的产率获得了多种芳基取代的产物。
• Direct Synthesis of <i>N</i> -Acyl Sulfonimidamides and <i>N</i> -Sulfonimidoyl Amidines from Sulfonimidoyl Azides
  作者：Ganesh Chandra Nandi、Irfana Jesin

  DOI：10.1002/adsc.201800215

  日期：2018.7.4

  demonstrate their utility in the construction of N‐acyl sulfonimidamides and N‐sulfonimidoyl amidines. N‐Acyl sulfonimidamides were synthesized in good to very good yields via “on water” copper‐catalyzed three‐component coupling between sulfonimidoyl azide, alkynes and water. The use of amines as nucleophiles yielded a wide range of N‐sulfonimidoyl amidines. Both reactions were completed in very short

  在这里，我们描述了磺酰亚胺基叠氮化物的制备，并证明了它们在N酰基磺酰亚胺酰胺和N磺酰亚胺基am的构建中的效用。N-酰基磺酰亚胺酰胺是通过磺酰亚胺基叠氮化物，炔烃和水之间的“水上”铜催化的三组分偶联以良好至非常高的产率合成的。使用胺作为亲核试剂可产生各种N-磺酰亚胺基yl。两种反应均在室温下于很短的条件下在很短的时间内完成，因此确立了磺酰亚胺基叠氮化物（磺酰叠氮基的氮杂类似物）的潜力，它是一步合成官能化磺酰胺基酰胺的极好前体。
• Constructing <i>N</i>-Acyl/<i>N</i>-Sulfonyl Aza-Sulfur Derivatives from Amides/Sulfonamides and Thiophthalimides via Oxidant Regulation
  作者：Yazhou Li、Yongkun Wang、Feifei Fang、Yu Zhang、Chunpu Li、Tao Yu、Qiangqiang Chen、Jiang Wang、Hong Liu

  DOI：10.1021/acs.orglett.3c02166

  日期：2023.8.18

  Here, we have constructed five distinct types of N-acyl or N-sulfonyl aza-sulfur scaffolds using readily available (sulfon)amides and thiophthalimides with precise regulation of oxidants. Our novel methods feature one-pot mild reaction conditions and simple operation, thereby making them highly convenient for the late-stage diversification of various amide drugs, bioactive molecules, and peptides.

  在这里，我们使用现成的（磺）酰胺和硫代邻苯二甲酰亚胺以及精确调节氧化剂构建了五种不同类型的N-酰基或N-磺酰基氮杂硫支架。我们的新方法具有一锅法反应条件温和、操作简单的特点，非常方便各种酰胺类药物、生物活性分子和肽的后期多样化。