erythro-N-(1-benzyl-2-hydroxy-2-phenethyl)benzamide | 66166-18-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: erythro-N-(1-benzyl-2-hydroxy-2-phenethyl)benzamide
• 英文别名: N-[(1R,2S)-1-hydroxy-1,3-diphenylpropan-2-yl]benzamide
• CAS: 66166-18-5；101708-93-4
• 化学式: C₂₂H₂₁NO₂
• 分子量: 331.414
• InChiKey: ZSARFWQBXNEIOJ-LEWJYISDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  cis-1-benzoyl-2-benzyl-3-phenylaziridine 在 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以91%的产率得到erythro-N-(1-benzyl-2-hydroxy-2-phenethyl)benzamide
  参考文献：
  名称：

  N-苯甲酰基氮丙啶光化学的物理方面：甲亚胺盐化物和相关光中间体的表征

  摘要：

  Results of a time-resolved study based on nanosecond laser flash photolysis are presented for phototransients derived from three N-benzoylaziridines in fluid solutions. The major transients, best assigned as azomethine ylides, are characterized by two maxima (380-440 and 560-610 nm) in the absorption spectrum in the visible region and by microsecond lifetimes at room temperature (tau(Y) = 0.2-31-mu-s); these are sluggish in their reactivity toward dimethyl acetylenedicarboxylate (k(q)Y less-than-or-equal-to 2 x 10(4) M-1 s-1 in benzene). Relatively short-lived triplets (tau(T) = 1-90 ns in benzene), 'quenchable by biphenyl and 2,5-dimethyl-2,4-hexadiene, act as precursors for the ylides. Between trans-1-benzoyl-2,3-diphenylaziridine (1a) and its cis isomer (1b), tau(T) is considerably shorter for the former (1 ns for 1a vs 40 ns for 1b, on the basis of the assumption that the rate constant for triplet quenching by 2,5-dimethyl-2,4-hexadiene is 2 x 10(9) M-1 s-1 in benzene); this is explainable in terms of efficient intramolecular quenching of the benzamide-type triplet by a beta-phenyl group in 1a while this interaction is less favorable in the most stable conformer of 1b (wherein the benzoyl moiety protrudes away from the cis phenyl groups). Steady-state photolysis and product analysis studies have provided evidence for photocleavage of both C-N and C-C bonds of the aziridine ring.

  DOI：

  10.1021/j100182a046

文献信息

• Oppong-Boachie, Francis Kwabena, Bulletin des Societes Chimiques Belges, 1985, vol. 94, # 4, p. 293 - 298
  作者：Oppong-Boachie, Francis Kwabena

  DOI：——

  日期：——
• KWABENA, OPPONG-BOACHIE, F., BULL. SOC. CHEM. BELG., 1985, 94, N 4, 293-298
  作者：KWABENA, OPPONG-BOACHIE, F.

  DOI：——

  日期：——