(2R,3S)-3-Amino-3-(2-furyl)-1-(p-methoxyphenyl)-2-methyl-1-propanone | 150716-65-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S)-3-Amino-3-(2-furyl)-1-(p-methoxyphenyl)-2-methyl-1-propanone
• 英文别名: (2R,3S)-3-amino-3-(furan-2-yl)-1-(4-methoxyphenyl)-2-methylpropan-1-one
• CAS: 150716-65-7
• 化学式: C₁₅H₁₇NO₃
• 分子量: 259.305
• InChiKey: LGCJUZZPCLSYKF-YGRLFVJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-Amino-3-(2-furyl)-1-(p-methoxyphenyl)-2-methyl-1-propanone 在 sodium hydroxide 、 红铝 作用下， 以 水 、 甲苯 、 叔丁醇 为溶剂， 生成 (1S,2R,3S)-3-<(tert-Butoxycarbonyl)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：

  <1-(p-Methoxyphenyl)propylidene>-p-tolylamine 在 sodium tetrahydroborate 、 硫酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (2R,3S)-3-Amino-3-(2-furyl)-1-(p-methoxyphenyl)-2-methyl-1-propanone
  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

• 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.