methyl N-[(E)-3-phenylprop-2-enylidene]carbamate | 111970-52-6

• 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: methyl N-[(E)-3-phenylprop-2-enylidene]carbamate
• CAS: 111970-52-6
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: WJOXOCNUHHYHBL-LWRNNSOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  三苯基硼烷 、 2-二氮杂-1-苯乙酮 、 methyl N-[(E)-3-phenylprop-2-enylidene]carbamate 以 二氯甲烷 为溶剂， 反应 6.0h， 以85%的产率得到methyl ((E)-5-oxo-1,4,5-triphenylpent-1-en-3-yl)carbamate
  参考文献：
  名称：

  Diastereoselective Three-Component Synthesis of β-Amino Carbonyl Compounds Using Diazo Compounds, Boranes, and Acyl Imines under Catalyst-Free Conditions

  摘要：

  Diazo compounds, boranes, and acyl imines undergo a three-component Mannich condensation reaction under catalyst-free conditions to give the anti beta-amino carbonyl compounds in high diastereoselectivity. The reaction tolerates a variety of functional groups, and an asymmetric variant was achieved using the (-)-phenylmenthol as chiral auxiliary in good yield and selectivity. These beta-amino carbonyl compounds are valuable intermediates, which can be transformed to many potential bioactive molecules.

  DOI：

  10.1021/jo5003505

文献信息

• Dinuclear Zinc-Catalyzed Enantioselective Aza-Henry Reaction
  作者：Barry M. Trost、David W. Lupton

  DOI：10.1021/ol070618e

  日期：2007.5.1

  The dinuclear zinc catalyst 1a was found to catalyze the addition of nitroalkanes to carbamate-protected imines. This aza-Henry reaction proceeds with high enantioselectivity when various carbamate-protected imines are used. alpha,beta-Unsaturated imines proved to be a particularly useful class of substrate routinely giving the alpha-nitro amine products in high enantiomeric excess.

  发现双核锌催化剂1a催化将硝基烷烃加到氨基甲酸酯保护的亚胺上。当使用各种氨基甲酸酯保护的亚胺时，该氮杂-亨利反应以高对映选择性进行。事实证明，α，β-不饱和亚胺是一类特别有用的底物，通常以高对映体过量的形式产生α-硝基胺产物。
• Multicomponent Mannich Reactions with Boron Enolates Derived from Diazo Esters and 9-BBN
  作者：Yi Luan、Scott E. Schaus

  DOI：10.1021/ol200766t

  日期：2011.5.6

  3-component Mannich condensation reaction. Catalyzed by Cu(II) salts, the reaction affords the corresponding isocyanate Mannich product: one that can be easily trapped in situ by other nucleophiles. The Mannich condensation corresponds to an α,α-disubstituted enolate addition to imines. The reaction was rendered asymmetric by using the (−)-phenylmenthol ester in good yield and selectivities.

  重氮酯、芳基硼烷和氨基甲酰亚胺会发生三组分曼尼希缩合反应。在 Cu(II) 盐的催化下，该反应产生相应的异氰酸酯曼尼希产物：一种很容易被其他亲核试剂原位捕获的产物。曼尼希缩合对应于亚胺上的α,α-二取代烯醇化物加成。通过使用 (-)-苯基薄荷醇酯使反应不对称，具有良好的产率和选择性。
• The enolate-imine condensation using lithium dianion of 3-hydroxybutanoate and N-acylaldimines: Enhanced stereoselectivlty by added lithium chloride
  作者：Minoru Hatanaka、Oee-Sook Park、Ikuo Ueda

  DOI：10.1016/s0040-4039(00)97317-9

  日期：1990.1

  An enolate-imine condensation using the lithium dianion of 3-hydroxy-butanoate and N-acylaldimines gave the key intermediate for the preparation of (+)-thienamycin with improved stereoselection in the presence of lithium chloride.
• Diastereoselective Three-Component Synthesis of β-Amino Carbonyl Compounds Using Diazo Compounds, Boranes, and Acyl Imines under Catalyst-Free Conditions
  作者：Yi Luan、Jie Yu、Xiaowei Zhang、Scott E. Schaus、Ge Wang

  DOI：10.1021/jo5003505

  日期：2014.5.16

  Diazo compounds, boranes, and acyl imines undergo a three-component Mannich condensation reaction under catalyst-free conditions to give the anti beta-amino carbonyl compounds in high diastereoselectivity. The reaction tolerates a variety of functional groups, and an asymmetric variant was achieved using the (-)-phenylmenthol as chiral auxiliary in good yield and selectivity. These beta-amino carbonyl compounds are valuable intermediates, which can be transformed to many potential bioactive molecules.