4-azido-2,4-dicyano-2-methyl-thiobutyric acid S-methyl ester | 927823-78-7

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物
• 英文名称: 4-azido-2,4-dicyano-2-methyl-thiobutyric acid S-methyl ester
• CAS: 927823-78-7
• 化学式: C₈H₉N₅OS
• 分子量: 223.258
• InChiKey: MFVXSZQGBFWTQP-POYBYMJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.0
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  113.41
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-azido-2,4-dicyano-2-methyl-thiobutyric acid S-methyl ester 在 (Me₂PO)2HPt(Me₂POH) 、 mercury(II) diacetate 咪唑 、 sodium tetrahydroborate 、 三甲基氯硅烷 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 74.5h， 生成
  参考文献：
  名称：

  Control of Diastereoselectivity in Tandem Asymmetric Reactions Generating Nonadjacent Stereocenters with Bifunctional Catalysis by Cinchona Alkaloids

  摘要：

  We report the manipulation of hydrogen-bonding-based cooperative catalysis to control the diastereoselectivity for a tandem asymmetric reaction creating two nonadjacent stereocenters. This ability to control both the enantioselectivity and diastereoselectivity allows, for the first time, the direct and stereoselective construction of 1,3-tertiary-quaternary stereocenters in any of the possible four configurations from the same prochiral precursors with catalytic control. The synthetic consequence of such catalyst-controlled construction of nonadjacent stereocenters is illustrated by the asymmetric synthesis of manzacidin C by using the same reaction sequence that was previously applied to the total synthesis of manzacidin A.

  DOI：

  10.1021/ja0670409
• 作为产物：
  描述：

  S-methyl 2-cyanothiopropionate 在 (R)-(6-hydroxyquinolin-4-yl)((2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl acetate sodium azide 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 138.0h， 生成 4-azido-2,4-dicyano-2-methyl-thiobutyric acid S-methyl ester
  参考文献：
  名称：

  Control of Diastereoselectivity in Tandem Asymmetric Reactions Generating Nonadjacent Stereocenters with Bifunctional Catalysis by Cinchona Alkaloids

  摘要：

  We report the manipulation of hydrogen-bonding-based cooperative catalysis to control the diastereoselectivity for a tandem asymmetric reaction creating two nonadjacent stereocenters. This ability to control both the enantioselectivity and diastereoselectivity allows, for the first time, the direct and stereoselective construction of 1,3-tertiary-quaternary stereocenters in any of the possible four configurations from the same prochiral precursors with catalytic control. The synthetic consequence of such catalyst-controlled construction of nonadjacent stereocenters is illustrated by the asymmetric synthesis of manzacidin C by using the same reaction sequence that was previously applied to the total synthesis of manzacidin A.

  DOI：

  10.1021/ja0670409