benzyl phenylsulfinylcarbamate | 1394013-24-1

• 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: benzyl phenylsulfinylcarbamate
• CAS: 1394013-24-1
• 化学式: C₁₄H₁₃NO₃S
• 分子量: 275.328
• InChiKey: RMHPDEWWONFDSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.64
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  benzyl phenylsulfinylcarbamate 在 N-氯代丁二酰亚胺 、 palladium 10% on activated carbon 、 chloro-(2-dicyclohexylphosphino-2’,6’-diisopropoxy-1,1‘-biphenyl)[2-(2-aminoethyl)phenyl] palladium(ll) methyl-tert-butyl ether adduct 、 氢气 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 47.5h， 生成 4-[S-phenyl-N-(pyridin-2-yl)sulfonimidoyl]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：

  sodium benzenesulfonate 在 正丁基锂 、 氯化亚砜 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.49h， 生成 benzyl phenylsulfinylcarbamate
  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

• 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。