(S)-N-(benzyloxycarbonyl)-4-methyl-4-carbomethoxy-Δ²-imidazoline | 190393-74-9

• 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: (S)-N-(benzyloxycarbonyl)-4-methyl-4-carbomethoxy-Δ²-imidazoline
• 英文别名: 3-O-benzyl 5-O-methyl (5S)-5-methyl-4H-imidazole-3,5-dicarboxylate
• CAS: 190393-74-9
• 化学式: C₁₄H₁₆N₂O₄
• 分子量: 276.292
• InChiKey: YLCLJLOTWOWFLB-AWEZNQCLSA-N

物化性质

• 沸点：
  379.7±52.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  68.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-N-(benzyloxycarbonyl)-4-methyl-4-carbomethoxy-Δ²-imidazoline 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 70.0 ℃ 、620.52 kPa 条件下， 反应 3.0h， 生成 (2S,5R,6S)-2,6-dimethyl-6-methoxy-2-carbomethoxy-1,4-diazabicyclo[3.2.0]-heptan-7-one
  参考文献：
  名称：

  Synthesis of Optically Active Imidazolines, Azapenams, Dioxocyclams, and Bis-dioxocyclams

  摘要：

  Optically active 4-methyl-4-carbomethoxy-Delta(2)-imidazoline was efficiently synthesized on a multigram scale. Photolysis with (methoxymethylcarbene)chromium complex produced the optically active azapenam in good yield and with high stereoselectivity. Acid-catalyzed dimerization followed by reduction produced the corresponding optically active dioxocyclam in good yield. Using a bis-carbene complex, an optically active bis-dioxocyclam was produced in excellent yield.

  DOI：

  10.1021/jo962343e
• 作为产物：
  描述：

  哌嗪,1-[2-甲基-1-(1-甲基乙基)丙基]-(9CI) 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 11.0h， 生成 (S)-N-(benzyloxycarbonyl)-4-methyl-4-carbomethoxy-Δ²-imidazoline
  参考文献：
  名称：

  Synthesis of Optically Active Imidazolines, Azapenams, Dioxocyclams, and Bis-dioxocyclams

  摘要：

  Optically active 4-methyl-4-carbomethoxy-Delta(2)-imidazoline was efficiently synthesized on a multigram scale. Photolysis with (methoxymethylcarbene)chromium complex produced the optically active azapenam in good yield and with high stereoselectivity. Acid-catalyzed dimerization followed by reduction produced the corresponding optically active dioxocyclam in good yield. Using a bis-carbene complex, an optically active bis-dioxocyclam was produced in excellent yield.

  DOI：

  10.1021/jo962343e

文献信息

• Synthesis of 5,12-Dioxocyclam Nickel (II) Complexes Having Quinoxaline Substituents at the 6 and 13 Positions as Potential DNA Bis-Intercalating and Cleaving Agents
  作者：Louis S. Hegedus、Marc M. Greenberg、Jory J. Wendling、Joseph P. Bullock

  DOI：10.1021/jo020708r

  日期：2003.5.1

  Several dioxocyclams containing quinoxaline moieties, as well as their nickel(II) complexes were synthesized and studied for their ability to bind and oxidatively cleave DNA. Although no evidence for binding by intercalation was found, the ability of the Ni(II) complexes to cleave DNA in the presence of Oxone was strongly dependent on both the nature and the spatial orientation of the quinoxaline moieties, suggesting at least transient association of these complexes with DNA.
• N-Functionalization of Poly(ethylene glycol)-Linked Mono- and Bis-dioxocyclams as Potential Ligands for Gd³⁺
  作者：Todd A. Brugel、L. S. Hegedus

  DOI：10.1021/jo030183i

  日期：2003.10.1

  A number of highly functionalized dioxocyclams with acetic acid side chains on the secondary amine sites and ethylene glycol side chains on 6 and 13-positions (12a, 12b) or a tetra(ethylene glycol) side chain linking the 6 and 13 positions (15) were synthesized and characterized, as was a bis-dioxocyclam bridged across the 6 and 13 positions by tetra(ethylene glycol) groups (16). These were screened for their ability to complex Gd3+. Only ligands 15 and 16, having tetra(ethylene glycol) groups, formed such complexes.
• Synthesis of Optically Active Imidazolines, Azapenams, Dioxocyclams, and Bis-dioxocyclams
  作者：Yi Hsiao、Louis S. Hegedus

  DOI：10.1021/jo962343e

  日期：1997.5.1

  Optically active 4-methyl-4-carbomethoxy-Delta(2)-imidazoline was efficiently synthesized on a multigram scale. Photolysis with (methoxymethylcarbene)chromium complex produced the optically active azapenam in good yield and with high stereoselectivity. Acid-catalyzed dimerization followed by reduction produced the corresponding optically active dioxocyclam in good yield. Using a bis-carbene complex, an optically active bis-dioxocyclam was produced in excellent yield.