N'-[(1S,2R)-2-cyano-1,2-diphenylpent-4-enyl]-4-(trifluoromethyl)benzohydrazide | 1264175-16-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: N'-[(1S,2R)-2-cyano-1,2-diphenylpent-4-enyl]-4-(trifluoromethyl)benzohydrazide
• CAS: 1264175-16-7
• 化学式: C₂₆H₂₂F₃N₃O
• 分子量: 449.475
• InChiKey: BBCDBAUFLVHMHL-UKILVPOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  64.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-苯基戊-4-烯-1-腈 在 正丁基锂 、 (4R,5R)-2-chloro-3,4-dimethyl-2-[(2-methylpropan-2-yl)oxy]-5-phenyl-1,3,2-oxazasilolidine 、 二异丙胺 作用下， 以 四氢呋喃 、 hexanes 、 苯 为溶剂， 反应 3.17h， 生成 N'-[(1S,2R)-2-cyano-1,2-diphenylpent-4-enyl]-4-(trifluoromethyl)benzohydrazide
  参考文献：
  名称：

  A New Synthesis of Pyrrolidines by Way of an Enantioselective Mannich/Diastereoselective Hydroamination Reaction Sequence

  摘要：

  A new two-step synthesis of highly substituted pyrrolidines has been developed. Chiral silane Lewis acid promoted enantioselective Mannich reactions of silyl ketene imines with acylhydrazones may be used to access bishomoallylic benzoic hydrazides that In turn may be cyclized to pyrrolidines by way of the thermal hydroamination reaction reported recently by Beauchemin. Importantly, excellent diastereoselectivity may be realized in the hydroamination reactions.

  DOI：

  10.1021/ol201566u

文献信息

• Highly Enantioselective Mannich Reactions with α-Aryl Silyl Ketene Acetals and Imines
  作者：Gregory T. Notte、Jenny M. Baxter Vu、James L. Leighton

  DOI：10.1021/ol103096u

  日期：2011.2.18

  Mannich reactions with chiral silicon Lewis acid activated acylhydrazones and α-aryl silyl ketene acetals and α-aryl,α-alkyl silyl ketene imines proceed efficiently and with good to excellent levels of both diastereoselectivity and enantioselectivity. The reactions provide access to α-aryl,β-hydrazido esters and α-aryl,α-alkyl,β-hydrazido nitriles, which are valuable analogs of β-amino acids.

  与手性硅路易斯酸活化的酰基腙和 α-芳基甲硅烷基乙烯酮缩醛和 α-芳基，α-烷基甲硅烷基乙烯酮亚胺的曼尼希反应有效地进行，并具有良好至极好的非对映选择性和对映选择性。该反应提供了获得 α-芳基、β-酰肼基酯和 α-芳基、α-烷基、β-酰肼基腈的途径，它们是 β-氨基酸的有价值的类似物。
• A New Synthesis of Pyrrolidines by Way of an Enantioselective Mannich/Diastereoselective Hydroamination Reaction Sequence
  作者：Jenny M. Baxter Vu、James L. Leighton

  DOI：10.1021/ol201566u

  日期：2011.8.5

  A new two-step synthesis of highly substituted pyrrolidines has been developed. Chiral silane Lewis acid promoted enantioselective Mannich reactions of silyl ketene imines with acylhydrazones may be used to access bishomoallylic benzoic hydrazides that In turn may be cyclized to pyrrolidines by way of the thermal hydroamination reaction reported recently by Beauchemin. Importantly, excellent diastereoselectivity may be realized in the hydroamination reactions.