2-(2-Furyl)-4-(p-methoxyphenyl)-3-methyl-4-(p-tolylamino)-1-aza-1,3-butadiene | 150716-67-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(2-Furyl)-4-(p-methoxyphenyl)-3-methyl-4-(p-tolylamino)-1-aza-1,3-butadiene
• CAS: 150716-67-9
• 化学式: C₂₂H₂₂N₂O₂
• 分子量: 346.429
• InChiKey: HPGFZNBGJZEDKX-FLDYAXOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.51
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  58.25
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(2-Furyl)-4-(p-methoxyphenyl)-3-methyl-4-(p-tolylamino)-1-aza-1,3-butadiene 在 sodium hydroxide 、 sodium tetrahydroborate 、 硫酸 、 二异丁基氢化铝 、 三氟乙酸 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 2.0h， 生成 (1R,2S,3S)-3-Amino-3-(2-furyl)-1-(p-methoxyphenyl)-2-methyl-1-propanol
  参考文献：
  名称：

  1,3-Amino alcohols from 4-amino-1-aza dienes. Diastereo- and enantioselective approach to the four diastereoisomers of the N-terminal amino acid component of nikkomycins B and BX

  摘要：

  A strategy that entails the preparation of 1,3-amino alcohols from 4-amino-1-aza dienes is used to synthesize the four diastereoisomeric lactones of the N-terminal amino acid moiety of nikkomycins B and B(X) in a diastereo- and enantioselective manner. Thus, enantiomerically pure beta-amino ketones anti-13 and syn-13 were synthesized starting from the 4-amino-1-aza diene 10 and (R)-O-benzyllactic aldehyde via the corresponding dihydro- and tetrahydropyrimidines. These beta-amino ketones were further converted into the lactones 22-25 with high diastereoselectivity through their 1,3-amino alcohol derivatives.

  DOI：

  10.1021/jo00074a024
• 作为产物：
  描述：

  2-氰基呋喃 、 <1-(p-Methoxyphenyl)propylidene>-p-tolylamine 生成 2-(2-Furyl)-4-(p-methoxyphenyl)-3-methyl-4-(p-tolylamino)-1-aza-1,3-butadiene
  参考文献：
  名称：

  1,3-Amino alcohols from 4-amino-1-aza dienes. Diastereo- and enantioselective approach to the four diastereoisomers of the N-terminal amino acid component of nikkomycins B and BX

  摘要：

  A strategy that entails the preparation of 1,3-amino alcohols from 4-amino-1-aza dienes is used to synthesize the four diastereoisomeric lactones of the N-terminal amino acid moiety of nikkomycins B and B(X) in a diastereo- and enantioselective manner. Thus, enantiomerically pure beta-amino ketones anti-13 and syn-13 were synthesized starting from the 4-amino-1-aza diene 10 and (R)-O-benzyllactic aldehyde via the corresponding dihydro- and tetrahydropyrimidines. These beta-amino ketones were further converted into the lactones 22-25 with high diastereoselectivity through their 1,3-amino alcohol derivatives.

  DOI：

  10.1021/jo00074a024

文献信息

• New synthesis of 4-amino-1-azadienes by addition of Zn-enolates to nitriles
  作者：José Barluenga、Carlos del Pozo Losada、Bernardo Olano

  DOI：10.1016/s0040-4039(00)73944-x

  日期：1993.1

  A synthesis of 4-amino-1-azadienes 1 b addition of Zn-enolates of Schiff bases to nitriles is described. This method improves the yields achieved by the former one using AlCl3.
• 1,3-Amino alcohols from 4-amino-1-aza dienes. Diastereo- and enantioselective approach to the four diastereoisomers of the N-terminal amino acid component of nikkomycins B and BX
  作者：Jose Barluenga、Argimiro L. Viado、Enrique Aguilar、Santos Fustero、Bernardo Olano

  DOI：10.1021/jo00074a024

  日期：1993.10

  A strategy that entails the preparation of 1,3-amino alcohols from 4-amino-1-aza dienes is used to synthesize the four diastereoisomeric lactones of the N-terminal amino acid moiety of nikkomycins B and B(X) in a diastereo- and enantioselective manner. Thus, enantiomerically pure beta-amino ketones anti-13 and syn-13 were synthesized starting from the 4-amino-1-aza diene 10 and (R)-O-benzyllactic aldehyde via the corresponding dihydro- and tetrahydropyrimidines. These beta-amino ketones were further converted into the lactones 22-25 with high diastereoselectivity through their 1,3-amino alcohol derivatives.