(S)-4-methyl-N-((3-nitrophenyl)(phenyl)methyl)benzenesulfonamide | 1112116-58-1

• 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: (S)-4-methyl-N-((3-nitrophenyl)(phenyl)methyl)benzenesulfonamide
• 英文别名: (S)-N-[(3-nitrophenyl)phenylmethyl]-4-methylbenzenesulfonamide
• CAS: 1112116-58-1
• 化学式: C₂₀H₁₈N₂O₄S
• 分子量: 382.44
• InChiKey: SHFIPDDHLLFEJZ-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  89.31
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  4-methyl-N-(3-nitrobenzylidene)benzenesulfonamide 、 苯硼酸 在 potassium phosphate monohydrate 、 (Pd((C₁₀H₆N₂C₇H₄CH₂C₆H₅)2)(H₂O)2)⁽²⁺⁾*2CF₃SO₃^(1-)=(Pd((C₁₀H₆N₂C₇H₄CH₂C₆H₅)2)(H₂O)2)(CF₃SO₃)2 作用下， 以 四氢呋喃 为溶剂， 生成 (R)-N-[(3-nitrophenyl)phenylmethyl]-4-methylbenzenesulfonamide 、 (S)-4-methyl-N-((3-nitrophenyl)(phenyl)methyl)benzenesulfonamide
  参考文献：
  名称：

  Catalytic Enantioselective Arylation of N-Tosylarylimines with Arylboronic Acids Using C₂-Symmetric Cationic N-Heterocyclic Carbene Pd²⁺ Diaquo Complexes

  摘要：

  The asymmetric arylation of N-tosylimines with arylboronic acids was realized by using chiral cationic C-2-symmetric N-heterocyclic carbene (NHC) Pd2+ diaquo complex 5b as the catalyst in combination with 1.0 equiv of K3PO4 center dot 3H(2)O in THF at 4 degrees C in the presence of powdered 4 angstrom MS to afford the corresponding adducts in excellent yields (up to 99%) and good to high enantioselectivities (up to 94% ee).

  DOI：

  10.1021/ol802861s

文献信息

• Palladium-Catalyzed Enantioselective Three-Component Synthesis of α-Substituted Amines
  作者：Tamara Beisel、Georg Manolikakes

  DOI：10.1021/acs.orglett.5b01502

  日期：2015.6.19

  palladium-catalyzed, enantioselective three-component synthesis of α-arylamines starting from sulfonamides, aldehydes, and arylboronic acids has been developed. These reactions generate a wide array of α-arylamines with high yields and enantioselectivities. Notably, this process is tolerant to air and moisture, providing an operationally simple approach for the synthesis of chiral α-arylamines.

  从磺酰胺，醛和芳基硼酸开始，已经开发了第一个常规的钯催化，对映选择性三组分合成α-芳基胺。这些反应产生高产率和对映选择性的多种α-芳基胺。值得注意的是，该方法耐受空气和湿气，为合成手性α-芳基胺提供了操作上简单的方法。