1-(2-chloro-2-cyano-ethyl)-2-oxo-cycloheptanecarbonitrile | 927824-22-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-chloro-2-cyano-ethyl)-2-oxo-cycloheptanecarbonitrile
• CAS: 927824-22-4
• 化学式: C₁₁H₁₃ClN₂O
• 分子量: 224.69
• InChiKey: CIKGPVOTOYZNNC-GXSJLCMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  64.65
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(2-chloro-2-cyano-ethyl)-2-oxo-cycloheptanecarbonitrile 在 盐酸 作用下， 反应 1.0h， 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：

  2-羰基-环庚烷甲腈 、 2-氯丙烯腈 在 N-[3,5-双(三氟甲基)苯基]-N′-[(9R)-6′-甲氧基-9-金鸡宁]硫脲 作用下， 以 甲苯 为溶剂， 反应 12.0h， 生成 1-(2-chloro-2-cyano-ethyl)-2-oxo-cycloheptanecarbonitrile 、 、 (1S)-1-[(2R)-2-chloro-2-cyanoethyl]-2-oxocycloheptane-1-carbonitrile
  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