N'-[(1R)-1-cyanopropyl]-4-nitrobenzohydrazide | 1200118-31-5

• 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'-[(1R)-1-cyanopropyl]-4-nitrobenzohydrazide
• CAS: 1200118-31-5
• 化学式: C₁₁H₁₂N₄O₃
• 分子量: 248.241
• InChiKey: SISDFUVHPKVWCU-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  三甲基氰硅烷 、 N’-(2-propylidene)-4-nitrobenzohydrazide 在 (R)-(-)-3,3'-bis(4-nitrophenyl)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate 、 叔丁醇 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以95%的产率得到N'-[(1R)-1-cyanopropyl]-4-nitrobenzohydrazide
  参考文献：
  名称：

  Asymmetric Hydrocyanation of Hydrazones Catalyzed by in Situ Formed O-Silylated BINOL-Phosphate: A Convenient Access to Versatile α-Hydrazino Acids

  摘要：

  A first organocatalytic enantioselective route was developed for the conversion of readily prepared and air stable aliphatic hydrazones to synthetically valuable alpha-hydrazinonitriles. This BINOL-phosphate catalyzed Strecker-type reaction (see scheme, Ar = p-NO2-Ph) provides a new practical and direct route to alpha-hydrazino acids of synthetic and biological importance. The actually active catalyst is proposed to be an In situ formed O-silylated BINOL-phosphate, thus shifting the nature of catalysis from Bronsted acid to Lewis acid organocatalysis.

  DOI：

  10.1021/ol9025974

文献信息

• Asymmetric Hydrocyanation of Hydrazones Catalyzed by in Situ Formed <i>O</i>-Silylated BINOL-Phosphate: A Convenient Access to Versatile α-Hydrazino Acids
  作者：Alexandru Zamfir、Svetlana B. Tsogoeva

  DOI：10.1021/ol9025974

  日期：2010.1.1

  A first organocatalytic enantioselective route was developed for the conversion of readily prepared and air stable aliphatic hydrazones to synthetically valuable alpha-hydrazinonitriles. This BINOL-phosphate catalyzed Strecker-type reaction (see scheme, Ar = p-NO2-Ph) provides a new practical and direct route to alpha-hydrazino acids of synthetic and biological importance. The actually active catalyst is proposed to be an In situ formed O-silylated BINOL-phosphate, thus shifting the nature of catalysis from Bronsted acid to Lewis acid organocatalysis.