N-(3,4-dimethoxyphenethyl)-1,1,1-trifluoromethanesulfonamide | 193689-60-0

• 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: N-(3,4-dimethoxyphenethyl)-1,1,1-trifluoromethanesulfonamide
• 英文别名: N-[2-(3,4-dimethoxyphenyl)ethyl]-1,1,1-trifluoromethanesulfonamide
• CAS: 193689-60-0
• 化学式: C₁₁H₁₄F₃NO₄S
• 分子量: 313.298
• InChiKey: KVKRDGOWPODPOP-UHFFFAOYSA-N

物化性质

• 沸点：
  357.1±52.0 °C(Predicted)
• 密度：
  1.344±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.69
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-(3,4-dimethoxyphenethyl)-1,1,1-trifluoromethanesulfonamide 在 sodium hydroxide 、 sodium hydride 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 {[2-(3,4-Dimethoxy-phenyl)-ethyl]-trifluoromethanesulfonyl-amino}-acetic acid
  参考文献：
  名称：

  Use of the Triflamide Group for Friedel-Crafts Acylation of N-(b-Phenethyl)amino Acids to 3-Benzazepine Derivatives

  摘要：

  Triflamides of N-(beta-phenethyl)amino acids (1) were treated with P2O5 under the Friedel-Crafts acylation conditions to give the 3-benzazepines in good yields. N-(beta-Phenethyl)-N-triflylvaline (If) and phenylglycine (1g) were efficiently prepared from the corresponding N-triflylamino acids and beta-phenethyl alcohol via the Mitsunobu reaction.

  DOI：

  10.3987/com-97-7803
• 作为产物：
  描述：

  三氟甲磺酸酐 、 3,4-二甲氧基苯乙胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以95%的产率得到N-(3,4-dimethoxyphenethyl)-1,1,1-trifluoromethanesulfonamide
  参考文献：
  名称：

  Palladium-Catalyzed [5 + 2] Heteroannulation of Phenethylamides with 1,3-Dienes to Dopaminergic 3-Benzazepines

  摘要：

  Phenethyltriflamides react with 1,3-dienes upon treatment with a catalytic amount of Pd(OAc)(2) and Cu(OAc)(2)/O-2 as oxidant to afford chemo-, regio- and diastereoselectively 2,3,4,5-tetrahydro-1H-benzo[d]azepines (3-benzazepine derivatives) in good to excellent yields. A DFT study of the [5 + 2] heteroannulation suggests a mechanistic pathway starting with formation of the six-membered palladacycle cis-PdX2L2 via a CMD process followed by eta(2) coordination and insertion of the 1,3-diene unit in a diastereoselective manner.

  DOI：

  10.1021/acs.orglett.0c01053

文献信息

• Use of the Triflamide Group for Friedel-Crafts Acylation of N-(b-Phenethyl)amino Acids to 3-Benzazepine Derivatives
  作者：Masami Kawase、Noboru Motohashi、Masayuki Niwa、Masakatsu Nozaki

  DOI：10.3987/com-97-7803

  日期：——

  Triflamides of N-(beta-phenethyl)amino acids (1) were treated with P2O5 under the Friedel-Crafts acylation conditions to give the 3-benzazepines in good yields. N-(beta-Phenethyl)-N-triflylvaline (If) and phenylglycine (1g) were efficiently prepared from the corresponding N-triflylamino acids and beta-phenethyl alcohol via the Mitsunobu reaction.
• Palladium-Catalyzed [5 + 2] Heteroannulation of Phenethylamides with 1,3-Dienes to Dopaminergic 3-Benzazepines
  作者：Álvaro Velasco-Rubio、Jesús A. Varela、Carlos Saá

  DOI：10.1021/acs.orglett.0c01053

  日期：2020.5.1

  Phenethyltriflamides react with 1,3-dienes upon treatment with a catalytic amount of Pd(OAc)(2) and Cu(OAc)(2)/O-2 as oxidant to afford chemo-, regio- and diastereoselectively 2,3,4,5-tetrahydro-1H-benzo[d]azepines (3-benzazepine derivatives) in good to excellent yields. A DFT study of the [5 + 2] heteroannulation suggests a mechanistic pathway starting with formation of the six-membered palladacycle cis-PdX2L2 via a CMD process followed by eta(2) coordination and insertion of the 1,3-diene unit in a diastereoselective manner.