2-[(S)-3-(3,5-Dimethyl-pyrazol-1-yl)-1-methyl-3-oxo-propyl]-malononitrile | 575489-80-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-[(S)-3-(3,5-Dimethyl-pyrazol-1-yl)-1-methyl-3-oxo-propyl]-malononitrile
• 英文别名: [(2S)-4-(3,5-Dimethyl-1H-pyrazol-1-yl)-4-oxobutan-2-yl]propanedinitrile；2-[(2S)-4-(3,5-dimethylpyrazol-1-yl)-4-oxobutan-2-yl]propanedinitrile
• CAS: 575489-80-4
• 化学式: C₁₂H₁₄N₄O
• 分子量: 230.269
• InChiKey: ZXMCNJQQOGBGIX-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  82.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  丙二腈 、 1-crotonoyl-3,5-dimethylpyrazole 在 2,2,6,6-四甲基哌啶 、 (R,R)-DBFOX-based Ni 、 乙酸酐 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 2-[(S)-3-(3,5-Dimethyl-pyrazol-1-yl)-1-methyl-3-oxo-propyl]-malononitrile 、 2-[(R)-3-(3,5-Dimethyl-pyrazol-1-yl)-1-methyl-3-oxo-propyl]-malononitrile
  参考文献：
  名称：

  Enantioselective Michael addition reactions of malononitrile catalyzed by chiral Lewis acid and achiral amine catalysts

  摘要：

  Reactions of malononitrile with 3-(2-alkenoyl)-2-oxazolidinones or 1-(2-alkenoyl)-4-bromo-3,5-dimethylpyrazoles can be doubly activated by the use of catalytic amounts (10 mol% each) of both, (R,R)-DBFOX/Ph-Ni(ClO4)(2)(.)3H(2)O and amines, to give the Michael adducts in high chemical yields with satisfactory enantioselectivities. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00084-3

文献信息

• Double catalytic enantioselective Michael addition reactions of tertiary nucleophile precursors—tertiary/quaternary and quaternary/quaternary carbon–carbon bond formations
  作者：Hiroshi Yanagita、Kazuhiro Kodama、Shuji Kanemasa

  DOI：10.1016/j.tetlet.2006.10.089

  日期：2006.12

  Enantioselective Michael addition reactions of tertiary nucleophile precursors, such as substituted malononitriles and cyclic 1,3-diketones, can be successfully activated by the metal complexes derived from R,R-DBFOX/Ph chiral ligand and cationic metal salts. With this method, the enantioselective tertiary/quaternary and quaternary/quaternary carbon–carbon bond formations can be achieved. Use of alcohol

  叔亲核体前体（如取代的丙二腈和环状1,3-二酮）的对映选择性Michael加成反应可以成功地由R，R -DBFOX / Ph手性配体和阳离子金属盐形成的金属络合物活化。用这种方法，可以实现对映选择性的叔/季和季/季碳-碳键的形成。使用醇类溶剂对成功至关重要，并且3,5-二甲基吡唑的α，β-不饱和酰胺比2-恶唑烷酮的受体更好。
• Enantioselective Michael addition reactions of malononitrile catalyzed by chiral Lewis acid and achiral amine catalysts
  作者：Kennosuke Itoh、Yoji Oderaotoshi、Shuji Kanemasa

  DOI：10.1016/s0957-4166(03)00084-3

  日期：2003.3

  Reactions of malononitrile with 3-(2-alkenoyl)-2-oxazolidinones or 1-(2-alkenoyl)-4-bromo-3,5-dimethylpyrazoles can be doubly activated by the use of catalytic amounts (10 mol% each) of both, (R,R)-DBFOX/Ph-Ni(ClO4)(2)(.)3H(2)O and amines, to give the Michael adducts in high chemical yields with satisfactory enantioselectivities. (C) 2003 Elsevier Science Ltd. All rights reserved.