(2E)-2-{[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methylidene}-4,4-dimethyl-3-oxopentanenitrile | 1107012-71-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2E)-2-{[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methylidene}-4,4-dimethyl-3-oxopentanenitrile
• CAS: 1107012-71-4
• 化学式: C₁₃H₁₉NO₃
• 分子量: 237.299
• InChiKey: LDWKSTZNEBURBA-ZKXNXJMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  59.32
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2E)-2-{[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methylidene}-4,4-dimethyl-3-oxopentanenitrile 、 ethyl N-{[(4-nitrobenzene)sulfonyl]oxy}carbamate 在 calcium oxide 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以55%的产率得到ethyl (2R,3S)-2-cyano-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(2,2-dimethylpropanoyl)aziridine-1-carboxylate
  参考文献：
  名称：

  One-pot synthesis of chiral multifunctionalized aziridines

  摘要：

  A direct synthetic procedure to obtain chiral aziridines is reported, involving a diastereoselective aza-MIRC (Michael Initiated Ring Closure) reaction. Multifunctionalized aziridines are obtained in high overall yields (82-92%) and with a diastereomeric ratio up to 99:1. Further synthetic elaboration can lead to the formation of interesting biochemical molecules, such as amino glycosides. The diastereomeric induction seems to be strongly controlled both by the choice of chiral moiety and by the electron withdrawing groups (EWG) present on the starting alkenes. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.11.017
• 作为产物：
  描述：

  新戊酰基乙腈 、 (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 在 哌啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以68%的产率得到(2E)-2-{[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methylidene}-4,4-dimethyl-3-oxopentanenitrile
  参考文献：
  名称：

  One-pot synthesis of chiral multifunctionalized aziridines

  摘要：

  A direct synthetic procedure to obtain chiral aziridines is reported, involving a diastereoselective aza-MIRC (Michael Initiated Ring Closure) reaction. Multifunctionalized aziridines are obtained in high overall yields (82-92%) and with a diastereomeric ratio up to 99:1. Further synthetic elaboration can lead to the formation of interesting biochemical molecules, such as amino glycosides. The diastereomeric induction seems to be strongly controlled both by the choice of chiral moiety and by the electron withdrawing groups (EWG) present on the starting alkenes. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.11.017