3-N-benzylamino-2-formylprop-2-enenitrile | 91025-00-2

• 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: 3-N-benzylamino-2-formylprop-2-enenitrile
• 英文别名: 3-(benzylamino)-2-formylprop-2-enenitrile
• CAS: 91025-00-2
• 化学式: C₁₁H₁₀N₂O
• 分子量: 186.213
• InChiKey: LVRHPZLFHVCEGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.38
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  52.89
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-N-benzylamino-2-formylprop-2-enenitrile 、 乙酰氯 在 吡啶 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 以65%的产率得到3-(N-acetyl-N-benzylamino)-2-formylprop-2-enenitrile
  参考文献：
  名称：

  Hetero-Diels-Alder reaction of propenenitriles with enol ethers: a convenient approach to functionalized 3,4-dihydro-2H-pyrans

  摘要：

  The hetero-Diels-Alder reaction of 3-(N-acetyl-N-benzylamino)-2-formylprop-2-enenitrile with enol ethers yielded cis/trans diastereoisomers of 2-alkoxy-4-amino-3,4-dihydro-2H-pyran-5-carbonitriles in moderate yields. Acidic hydrolysis of cis-diastereoisomer in concentrated sulfuric acid gave 2-oxo-1,2-dihydropyrydine-3-carbaldehyde. The reaction of 2-benzoyl-3-heteroaromaticprop-2-enenitriles with enol ethers afforded diastereoisomeric cis/trans cycloadducts in good yields. The structure of the products is discussed in terms of configuration and preferred conformation.

  DOI：

  10.1007/s00706-007-0824-x
• 作为产物：
  描述：

  苄胺 、 α-Cyano-β-dimethylamino-acrolein 以 二氯甲烷 为溶剂， 反应 1.0h， 以52%的产率得到3-N-benzylamino-2-formylprop-2-enenitrile
  参考文献：
  名称：

  Hetero-Diels-Alder reaction of propenenitriles with enol ethers: a convenient approach to functionalized 3,4-dihydro-2H-pyrans

  摘要：

  The hetero-Diels-Alder reaction of 3-(N-acetyl-N-benzylamino)-2-formylprop-2-enenitrile with enol ethers yielded cis/trans diastereoisomers of 2-alkoxy-4-amino-3,4-dihydro-2H-pyran-5-carbonitriles in moderate yields. Acidic hydrolysis of cis-diastereoisomer in concentrated sulfuric acid gave 2-oxo-1,2-dihydropyrydine-3-carbaldehyde. The reaction of 2-benzoyl-3-heteroaromaticprop-2-enenitriles with enol ethers afforded diastereoisomeric cis/trans cycloadducts in good yields. The structure of the products is discussed in terms of configuration and preferred conformation.

  DOI：

  10.1007/s00706-007-0824-x

文献信息

• Hetero-Diels-Alder reaction of propenenitriles with enol ethers: a convenient approach to functionalized 3,4-dihydro-2H-pyrans
  作者：Aleksandra Pałasz、Krystyna Bogdanowicz-Szwed

  DOI：10.1007/s00706-007-0824-x

  日期：2008.6

  The hetero-Diels-Alder reaction of 3-(N-acetyl-N-benzylamino)-2-formylprop-2-enenitrile with enol ethers yielded cis/trans diastereoisomers of 2-alkoxy-4-amino-3,4-dihydro-2H-pyran-5-carbonitriles in moderate yields. Acidic hydrolysis of cis-diastereoisomer in concentrated sulfuric acid gave 2-oxo-1,2-dihydropyrydine-3-carbaldehyde. The reaction of 2-benzoyl-3-heteroaromaticprop-2-enenitriles with enol ethers afforded diastereoisomeric cis/trans cycloadducts in good yields. The structure of the products is discussed in terms of configuration and preferred conformation.