(3E)-3-ethylidene-1-(4-methoxybenzyl)-4-methyl(15N)pyrrolidine-2,5-dione | 1219938-61-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (3E)-3-ethylidene-1-(4-methoxybenzyl)-4-methyl(15N)pyrrolidine-2,5-dione
• CAS: 1219938-61-0
• 化学式: C₁₅H₁₇NO₃
• 分子量: 260.298
• InChiKey: ZUYPLBHAUPDTPE-QUDGBDCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.15
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3E)-3-ethylidene-1-(4-methoxybenzyl)-4-methyl(15N)pyrrolidine-2,5-dione 在 ammonium cerium (IV) nitrate 、 一水合肼 作用下， 以 水 、 乙腈 、 甲醇 为溶剂， 反应 3.08h， 以13%的产率得到(3E)-3-ethylidene-4-methyl(15N)pyrrolidine-2,5-dione
  参考文献：
  名称：

  Phytochrome as Molecular Machine: Revealing Chromophore Action during the Pfr → Pr Photoconversion by Magic-Angle Spinning NMR Spectroscopy

  摘要：

  The cyanobacterial phytochrome Cph1 can be photoconverted between two thermally stable states, Pr and Pfr. The photochemically induced Pfr -> Pr back-reaction has been followed at low temperature by magic-angle spinning (MAS) NMR spectroscopy, allowing two intermediates, Lumi-F and Meta-F, to be trapped. Employing uniformly C-13- and N-15-labeled open-chain tetrapyrrole chromophores, all four states Pfr, Lumi-F, Meta-F, and Pr-have been structurally characterized. In the first step, the double bond. photoisomerization forming Lumi-F occurs. The second step, the transformation to Meta-F, is driven by the release of the mechanical tension. This process leads to the break of the hydrogen bond of the ring D nitrogen to Asp-207 and triggers signaling. The third step is protonically driven allowing the hydrogen-bonding interaction of the ring D nitrogen to be restored. Compared to the forward reaction, the order of events is changed, probably caused by the different properties of the hydrogen bonding partners of N24, leading to the directionality of the photocycle.

  DOI：

  10.1021/ja9108616
• 作为产物：
  描述：

  硝基乙烷 、 1-(4-methoxybenzyl)-3-methyl(15N)-1H-pyrrole-2.5-dione 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 1.0h， 以44%的产率得到(3E)-3-ethylidene-1-(4-methoxybenzyl)-4-methyl(15N)pyrrolidine-2,5-dione
  参考文献：
  名称：

  Phytochrome as Molecular Machine: Revealing Chromophore Action during the Pfr → Pr Photoconversion by Magic-Angle Spinning NMR Spectroscopy

  摘要：

  The cyanobacterial phytochrome Cph1 can be photoconverted between two thermally stable states, Pr and Pfr. The photochemically induced Pfr -> Pr back-reaction has been followed at low temperature by magic-angle spinning (MAS) NMR spectroscopy, allowing two intermediates, Lumi-F and Meta-F, to be trapped. Employing uniformly C-13- and N-15-labeled open-chain tetrapyrrole chromophores, all four states Pfr, Lumi-F, Meta-F, and Pr-have been structurally characterized. In the first step, the double bond. photoisomerization forming Lumi-F occurs. The second step, the transformation to Meta-F, is driven by the release of the mechanical tension. This process leads to the break of the hydrogen bond of the ring D nitrogen to Asp-207 and triggers signaling. The third step is protonically driven allowing the hydrogen-bonding interaction of the ring D nitrogen to be restored. Compared to the forward reaction, the order of events is changed, probably caused by the different properties of the hydrogen bonding partners of N24, leading to the directionality of the photocycle.

  DOI：

  10.1021/ja9108616