(S)-N-((3-bromophenyl)(phenyl)methyl)-4-methylbenzenesulfonamide | 1112116-44-5

• 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)-N-((3-bromophenyl)(phenyl)methyl)-4-methylbenzenesulfonamide
• 英文别名: N-[(S)-(3-bromophenyl)-phenylmethyl]-4-methylbenzenesulfonamide
• CAS: 1112116-44-5
• 化学式: C₂₀H₁₈BrNO₂S
• 分子量: 416.338
• InChiKey: HEVURKSDSUDQKD-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-[1-(3-Bromo-phenyl)-meth-(E)-ylidene]-4-methyl-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， 以85%的产率得到(S)-N-((3-bromophenyl)(phenyl)methyl)-4-methylbenzenesulfonamide
  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。
• Catalytic Enantioselective Arylation of <i>N</i>-Tosylarylimines with Arylboronic Acids Using <i>C</i>₂-Symmetric Cationic <i>N</i>-Heterocyclic Carbene Pd²⁺ Diaquo Complexes
  作者：Guang-Ning Ma、Tao Zhang、Min Shi

  DOI：10.1021/ol802861s

  日期：2009.2.19

  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).
• Development of New <i>P</i>-Chiral <i>P</i>,π-Dihydrobenzooxaphosphole Hybrid Ligands for Asymmetric Catalysis
  作者：Joshua D. Sieber、Divya Chennamadhavuni、Keith R. Fandrick、Bo Qu、Zhengxu S. Han、Jolaine Savoie、Shengli Ma、Lalith P. Samankumara、Nelu Grinberg、Heewon Lee、Jinhua J. Song、Chris H. Senanayake

  DOI：10.1021/ol5027798

  日期：2014.10.17

  A new family of P-chiral P,π-hybrid ligands was prepared from the dihydrobenzooxaphosphole core. These new ligands were demonstrated to be both sterically and electronically tunable at the substituents on the phosphorus atom and the π-system of the ligand. Application of these new ligands to the catalytic asymmetric addition of boronic acids to imine electrophiles was shown to proceed with high levels of enantioinduction.