4-[S-phenyl-N-(pyrimidin-5-yl)sulfonimidoyl]morpholine | 1394013-41-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-[S-phenyl-N-(pyrimidin-5-yl)sulfonimidoyl]morpholine
• 英文别名: Morpholin-4-yl-oxo-phenyl-pyrimidin-5-ylimino-lambda6-sulfane；morpholin-4-yl-oxo-phenyl-pyrimidin-5-ylimino-λ6-sulfane
• CAS: 1394013-41-2
• 化学式: C₁₄H₁₆N₄O₂S
• 分子量: 304.373
• InChiKey: NYWGFOXVMDJUSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  76.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  benzenesulfinamide 在 N-氯代丁二酰亚胺 、 正丁基锂 、 chloro-(2-dicyclohexylphosphino-2’,6’-diisopropoxy-1,1‘-biphenyl)[2-(2-aminoethyl)phenyl] palladium(ll) methyl-tert-butyl ether adduct 、 三氟乙酸 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 47.83h， 生成 4-[S-phenyl-N-(pyrimidin-5-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

文献信息

• A mild and efficient copper-catalyzed N-arylation of unprotected sulfonimidamides using boronic acids
  作者：S.R.K. Battula、G.V. Subbareddy、I.E. Chakravarthy

  DOI：10.1016/j.tetlet.2013.11.084

  日期：2014.1

  An efficient and low cost copper catalyzed system for N-arylation of sulfonimidamides has been developed. The reaction proceeds at room temperature under base free conditions. Various N-aryl, N-heteroaryl, and N-cyclopropyl sulfonimidamides were obtained in good to excellent yields. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis and arylation of unprotected sulfonimidamides
  作者：Matías Funes Maldonado、Fernando Sehgelmeble、Fanny Bjarnemark、Mats Svensson、Jens Åhman、Per I. Arvidsson

  DOI：10.1016/j.tet.2012.06.072

  日期：2012.9

  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.