(E)-N-(1-(4-methoxyphenyl)-4,4-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pent-2-enyl)pyridine-2-sulfonamide | 1346951-15-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (E)-N-(1-(4-methoxyphenyl)-4,4-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pent-2-enyl)pyridine-2-sulfonamide
• CAS: 1346951-15-2
• 化学式: C₂₅H₃₅BN₂O₅S
• 分子量: 486.44
• InChiKey: YUQCMRLZILBRSB-JZJYNLBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.71
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  86.75
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (E)-N-(1-(4-methoxyphenyl)-4,4-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pent-2-enyl)pyridine-2-sulfonamide 在 sodium perborate monohydrate 作用下， 以 四氢呋喃 、 水 为溶剂， 以87%的产率得到N-(1-(4-methoxyphenyl)-4,4-dimethyl-2-oxopentyl)pyridine-2-sulfonamide
  参考文献：
  名称：

  Stereoselective Vinylation of Aryl N-(2-Pyridylsulfonyl) Aldimines with 1-Alkenyl-1,1-heterobimetallic Reagents

  摘要：

  Vinylation of aryl N-(2-pyridylsulfonyl) aldimines with versatile 1-alkenyl-1,1-borozinc heterobimetallic reagents is disclosed. In situ hydroboration of air-stable B(pin)-alkynes followed by chemoselective transmetalation with dimethylzinc and addition to aldimines provides B(pin)-substituted allylic amines in 53-93% yield in a one-pot procedure. The addition step can be followed by either B-C bond oxidation to provide alpha-amino ketones (71-98% yield) or Suzuki cross-coupling to furnish trisubstituted 2-arylated (E)-allylic amines (51-73% yield).

  DOI：

  10.1021/ol202766g
• 作为产物：
  描述：

  N-(4-methoxybenzylidene)pyridine-2-sulfonamide 、 2-(3,3-dimethylbut-1-yn-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 在 bis(cyclohexanyl)borane 、 Dimethylzinc 作用下， 以 甲苯 、 二氯甲烷 为溶剂， 反应 0.5h， 以60%的产率得到(E)-N-(1-(4-methoxyphenyl)-4,4-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pent-2-enyl)pyridine-2-sulfonamide
  参考文献：
  名称：

  Stereoselective Vinylation of Aryl N-(2-Pyridylsulfonyl) Aldimines with 1-Alkenyl-1,1-heterobimetallic Reagents

  摘要：

  Vinylation of aryl N-(2-pyridylsulfonyl) aldimines with versatile 1-alkenyl-1,1-borozinc heterobimetallic reagents is disclosed. In situ hydroboration of air-stable B(pin)-alkynes followed by chemoselective transmetalation with dimethylzinc and addition to aldimines provides B(pin)-substituted allylic amines in 53-93% yield in a one-pot procedure. The addition step can be followed by either B-C bond oxidation to provide alpha-amino ketones (71-98% yield) or Suzuki cross-coupling to furnish trisubstituted 2-arylated (E)-allylic amines (51-73% yield).

  DOI：

  10.1021/ol202766g