threo-Benzenesulfonic acid 1-isopropyl-2-<(4-methoxyphenyl)carbamoyl>propyl ester

• 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: threo-Benzenesulfonic acid 1-isopropyl-2-<(4-methoxyphenyl)carbamoyl>propyl ester
• 英文别名: threo-Benzenesulfonic acid 1-isopropyl-2-[(4-methoxyphenyl)carbamoyl]propyl ester；[(2R,3R)-1-(4-methoxyanilino)-2,4-dimethyl-1-oxopentan-3-yl] benzenesulfonate
• 化学式: C₂₀H₂₅NO₅S
• 分子量: 391.488
• InChiKey: CBJSJHHGXPCVRZ-DNVCBOLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  90.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  threo-Benzenesulfonic acid 1-isopropyl-2-<(4-methoxyphenyl)carbamoyl>propyl ester 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以91%的产率得到(3S,4R)-4-Isopropyl-1-(4-methoxy-phenyl)-3-methyl-azetidin-2-one
  参考文献：
  名称：

  2-Iminooxetane Chemistry. 4. Synthesis of .beta.-Substituted Propionamides

  摘要：

  beta-substituted propionamides (RCHXCR(1)R(2)CONHAr) were synthesized in high yields by addition of protic and aprotic Lewis acids (C6H5SO3H, CF3COOH, CH3COOH, HI, MgBr2, ZnI2, CH3OH, H2O,2,4,6-(NO2)(3)C6H2OH) to 2-iminooxetanes. Studies on the stereochemistry of the acid addition to unsymmetrically C3,C4-monosubstituted 2-iminooxetanes indicate that product distribution depends on the steric and electronic nature of the substitutents of the oxetane moiety as well as on the nucleophilicity of the conjugate base derived from the acid.

  DOI：

  10.1021/jo00083a036
• 作为产物：
  描述：

  cis-2-<(4-Methoxyphenyl)imino>-3-methyl-4-isopropyloxethane 、 苯磺酸 以 二氯甲烷 为溶剂， 反应 30.0h， 以91%的产率得到threo-Benzenesulfonic acid 1-isopropyl-2-<(4-methoxyphenyl)carbamoyl>propyl ester
  参考文献：
  名称：

  2-Iminooxetane Chemistry. 4. Synthesis of .beta.-Substituted Propionamides

  摘要：

  beta-substituted propionamides (RCHXCR(1)R(2)CONHAr) were synthesized in high yields by addition of protic and aprotic Lewis acids (C6H5SO3H, CF3COOH, CH3COOH, HI, MgBr2, ZnI2, CH3OH, H2O,2,4,6-(NO2)(3)C6H2OH) to 2-iminooxetanes. Studies on the stereochemistry of the acid addition to unsymmetrically C3,C4-monosubstituted 2-iminooxetanes indicate that product distribution depends on the steric and electronic nature of the substitutents of the oxetane moiety as well as on the nucleophilicity of the conjugate base derived from the acid.

  DOI：

  10.1021/jo00083a036