N-(benzoyloxy)-N-((S)-1-phenylallyl)benzamide

• 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-(benzoyloxy)-N-((S)-1-phenylallyl)benzamide
• 英文别名: [benzoyl-[(1S)-1-phenylprop-2-enyl]amino] benzoate
• 化学式: C₂₃H₁₉NO₃
• 分子量: 357.409
• InChiKey: YFRSAYGVZJYEBI-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(苯甲酰氧基)苯甲酰胺 、 (E)-cinnamyl diethyl phosphate 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 2,6-二[(4S)-4-苯基-2-恶唑啉基]吡啶 cesium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 N-(benzoyloxy)-N-((R)-1-phenylallyl)benzamide 、 N-(benzoyloxy)-N-((S)-1-phenylallyl)benzamide 、 N-(benzoyloxy)-N-cinnamylbenzamide
  参考文献：
  名称：

  Utility of the Iridium Complex of the Pybox Ligand in Regio- and Enantioselective Allylic Substitution

  摘要：

  [GRAPHICS]The viability of the iridium complex of pybox as chiral catalyst in allylic substitutions and the enantiosilective synthesis of branched products was studied. Among several chiral ligands evaluated, the iridium complex of pybox having a phenyl group catalyzed the reaction with high activity to form the branched amines with good enantioselectivities when hydroxylamine, amine, and aniline were employed as a nucleophile. The allylic substitution with oximes proceeded smoothly to give the branched oxime ethers with good enantioselectivities.

  DOI：

  10.1021/ol047915t

文献信息

• Regio- and Enantioselective Allylic Substitution with Less Active N- or O-Nucleophiles Catalyzed by Iridium-Complex of Bis(oxazolinyl)pyridine
  作者：Hideto Miyabe、Katsuhiko Moriyama、Yoshiji Takemoto

  DOI：10.1248/cpb.59.714

  日期：——

  The utility of hydroxylamines as nitrogen nucleophiles was investigated in the iridium-catalyzed regio- and enantioselective allylic substitution. Allylic substitution with hydroxylamines proceeded with good enantioselectivities by using the iridium-complex of bis(oxazolinyl)pyridine ligand. The good regio- and enantioselectivities were also achieved in the reaction with alkylamines, p-anisidine, and 4-methoxyphenol.

  研究了羟胺作为氮亲核物在铱催化的区域和对映选择性烯丙基取代中的作用。通过使用双（噁唑啉基）吡啶配体的铱络合物，羟胺的烯丙基取代反应具有良好的对映选择性。在与烷基胺、对甲氧基苯胺和 4-甲氧基苯酚的反应中也实现了良好的区域和对映选择性。