dimethyl cis-1-benzoyl-2,5-diphenyl-3-pyrrolidine-3,4-dicarboxylate | 138312-60-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: dimethyl cis-1-benzoyl-2,5-diphenyl-3-pyrrolidine-3,4-dicarboxylate
• CAS: 138312-60-4
• 化学式: C₂₇H₂₃NO₅
• 分子量: 441.483
• InChiKey: YESBEYBDKWWBPN-PSWAGMNNSA-N

物化性质

• 沸点：
  600.1±55.0 °C(Predicted)
• 密度：
  1.262±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  33.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  72.91
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  dimethyl cis-1-benzoyl-2,5-diphenyl-3-pyrrolidine-3,4-dicarboxylate 在 nickel(IV) oxide 作用下， 以 苯 为溶剂， 反应 3.0h， 以65%的产率得到dimethyl 2,5-diphenyl-1H-pyrrole-3,4-dicarboxylate
  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
• 作为产物：
  描述：

  cis-1-benzoyl-2,3-diphenylaziridine 、 丁炔二酸二甲酯 以 乙腈 为溶剂， 反应 2.5h， 以38%的产率得到二苯基乙酮
  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