(2R)-2-amino-3-phenyl-N-quinolin-8-ylpropanamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R)-2-amino-3-phenyl-N-quinolin-8-ylpropanamide
• 化学式: C₁₈H₁₇N₃O
• 分子量: 291.352
• InChiKey: LJSVCTGYPKVGIN-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.74
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  68.01
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2R)-2-amino-3-phenyl-N-quinolin-8-ylpropanamide 在 吡啶 、 4-羟基香豆素 、 palladium diacetate 、 溶剂黄146 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 64.0h， 生成
  参考文献：
  名称：

  Tridentate Directing Groups Stabilize 6-Membered Palladacycles in Catalytic Alkene Hydrofunctionalization

  摘要：

  Removable tridentate directing groups inspired by pincer ligands have been designed to stabilize otherwise kinetically and thermodynamically disfavored 6-membered alkyl palladacycle intermediates. This family of directing groups enables regioselective remote hydrocarbofunctionalization of several synthetically useful alkene-containing substrate classes, including 4-pentenoic acids, allylic alcohols, homoallyl amines, and bis-homoallylamiries, under Pd(II) catalysis. In conjunction with previous findings, we demonstrate regiodivergent hydro-functionalization of 34Dutenoic acid derivatives to afford either Markovnikov or anti-Markovnikov addition products depending on directing group choice. Preliminary mechanistic and computational data are presented to support the proposed catalytic cycle.

  DOI：

  10.1021/jacs.7b08383
• 作为产物：
  描述：

  BOC-L-苯丙氨酸 在 氯甲酸乙酯 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 33.0h， 生成 (2R)-2-amino-3-phenyl-N-quinolin-8-ylpropanamide
  参考文献：
  名称：

  Tridentate Directing Groups Stabilize 6-Membered Palladacycles in Catalytic Alkene Hydrofunctionalization

  摘要：

  Removable tridentate directing groups inspired by pincer ligands have been designed to stabilize otherwise kinetically and thermodynamically disfavored 6-membered alkyl palladacycle intermediates. This family of directing groups enables regioselective remote hydrocarbofunctionalization of several synthetically useful alkene-containing substrate classes, including 4-pentenoic acids, allylic alcohols, homoallyl amines, and bis-homoallylamiries, under Pd(II) catalysis. In conjunction with previous findings, we demonstrate regiodivergent hydro-functionalization of 34Dutenoic acid derivatives to afford either Markovnikov or anti-Markovnikov addition products depending on directing group choice. Preliminary mechanistic and computational data are presented to support the proposed catalytic cycle.

  DOI：

  10.1021/jacs.7b08383