{2-[4-(3,3-Dimethyl-ureido)-benzenesulfonylamino]-ethyl}-carbamic acid tert-butyl ester | 279681-00-4

• 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: {2-[4-(3,3-Dimethyl-ureido)-benzenesulfonylamino]-ethyl}-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[2-[[4-(dimethylcarbamoylamino)phenyl]sulfonylamino]ethyl]carbamate
• CAS: 279681-00-4
• 化学式: C₁₆H₂₆N₄O₅S
• 分子量: 386.472
• InChiKey: JLPZIPPAWHTANW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  {2-[4-(3,3-Dimethyl-ureido)-benzenesulfonylamino]-ethyl}-carbamic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到N-(2-Amino-ethyl)-4-(3,3-dimethyl-ureido)-benzenesulfonamide
  参考文献：
  名称：

  Low-Temperature Turnover Control of Photosystem II Using Novel Metal-Containing Redox-Active Herbicides

  摘要：

  A novel approach of using metal-containing redox-active herbicides to prepare and study the light-induced intermediates of the photosystern II (PSII) photocycle is described. The redox-active herbicides feature an iron(III) ethylenediuninetetracetate [Fe-III-(EDTA)] electron-acceptor group linked to a Q(B)-site binding dimethylphenylurea moiety by a hydrocarbon spacer. Like the nitroxyl-based redox-active herbicides previously described (Bocarsly, J. R.; Brudvig, G. W. J. Am. Chem. Sec. 1992, 114, 9762-9767), metal-containing herbicides accept electrons from the donor side of PSII while bound to the Q(B) site and restrict the S-state cycling to two stable charge separations. The use of Fe-III-(EDTA) as an electron acceptor allows turnover at low temperatures. EPR studies of PSII upon continuous illumination at 225 K with 0.7 mM of redox-active herbicide, Fe-III-(EDTA) linked by an ethane spacer to a dimethylphenyl urea group (2), produced a stable two-step S-1 to S-3 advance of the O-2-evolving complex (OEC) and a stoichiometric reduction of the Fe-III-(EDTA) moiety of the herbicide, while a control sample with 0.02 InM DCMU [3-(3,4-dichlorophenyl)-1,1-dimethyl-urea] and 0.7 mM of 4 exhibited only a one-step SI to St advance of the OEC without significant reduction of the Fe-III-(EDTA) moiety of the herbicide. Similar EPR results were obtained for 7, Fe-III-(EDTA) linked Ca the dimethylphenylurea group by a pentane spacer. O-2-evolution inhibition studies show that appending the Fe-III-(EDTA) moiety to the phenylurea herbicide causes a significant decrease in the binding affinity compared to that of DCMU. On the basis of O-2-evolution studies with various herbicide derivatives and different PSII sample types, the observed decrease in binding affinities is attributed to the degree of accessibility of the Q(B)-binding pocket to the herbicides and to electrostatic and hydrophilicity factors. The present study describes the use of novel metal-containing herbicides in studying long-range electron transfer in PSII and in trapping photogenerated two-electron oxidized intermediate states of the O-2-evolving complex.

  DOI：

  10.1021/ja994138x
• 作为产物：
  描述：

  2-(叔丁氧羰基氧亚氨基)-2-苯乙腈 以 四氢呋喃 为溶剂， 反应 2.33h， 生成 {2-[4-(3,3-Dimethyl-ureido)-benzenesulfonylamino]-ethyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Low-Temperature Turnover Control of Photosystem II Using Novel Metal-Containing Redox-Active Herbicides

  摘要：

  A novel approach of using metal-containing redox-active herbicides to prepare and study the light-induced intermediates of the photosystern II (PSII) photocycle is described. The redox-active herbicides feature an iron(III) ethylenediuninetetracetate [Fe-III-(EDTA)] electron-acceptor group linked to a Q(B)-site binding dimethylphenylurea moiety by a hydrocarbon spacer. Like the nitroxyl-based redox-active herbicides previously described (Bocarsly, J. R.; Brudvig, G. W. J. Am. Chem. Sec. 1992, 114, 9762-9767), metal-containing herbicides accept electrons from the donor side of PSII while bound to the Q(B) site and restrict the S-state cycling to two stable charge separations. The use of Fe-III-(EDTA) as an electron acceptor allows turnover at low temperatures. EPR studies of PSII upon continuous illumination at 225 K with 0.7 mM of redox-active herbicide, Fe-III-(EDTA) linked by an ethane spacer to a dimethylphenyl urea group (2), produced a stable two-step S-1 to S-3 advance of the O-2-evolving complex (OEC) and a stoichiometric reduction of the Fe-III-(EDTA) moiety of the herbicide, while a control sample with 0.02 InM DCMU [3-(3,4-dichlorophenyl)-1,1-dimethyl-urea] and 0.7 mM of 4 exhibited only a one-step SI to St advance of the OEC without significant reduction of the Fe-III-(EDTA) moiety of the herbicide. Similar EPR results were obtained for 7, Fe-III-(EDTA) linked Ca the dimethylphenylurea group by a pentane spacer. O-2-evolution inhibition studies show that appending the Fe-III-(EDTA) moiety to the phenylurea herbicide causes a significant decrease in the binding affinity compared to that of DCMU. On the basis of O-2-evolution studies with various herbicide derivatives and different PSII sample types, the observed decrease in binding affinities is attributed to the degree of accessibility of the Q(B)-binding pocket to the herbicides and to electrostatic and hydrophilicity factors. The present study describes the use of novel metal-containing herbicides in studying long-range electron transfer in PSII and in trapping photogenerated two-electron oxidized intermediate states of the O-2-evolving complex.

  DOI：

  10.1021/ja994138x

文献信息

• Low-Temperature Turnover Control of Photosystem II Using Novel Metal-Containing Redox-Active Herbicides
  作者：Laba Karki、K. V. Lakshmi、Veronika A. Szalai、Gary W. Brudvig

  DOI：10.1021/ja994138x

  日期：2000.5.1

  A novel approach of using metal-containing redox-active herbicides to prepare and study the light-induced intermediates of the photosystern II (PSII) photocycle is described. The redox-active herbicides feature an iron(III) ethylenediuninetetracetate [Fe-III-(EDTA)] electron-acceptor group linked to a Q(B)-site binding dimethylphenylurea moiety by a hydrocarbon spacer. Like the nitroxyl-based redox-active herbicides previously described (Bocarsly, J. R.; Brudvig, G. W. J. Am. Chem. Sec. 1992, 114, 9762-9767), metal-containing herbicides accept electrons from the donor side of PSII while bound to the Q(B) site and restrict the S-state cycling to two stable charge separations. The use of Fe-III-(EDTA) as an electron acceptor allows turnover at low temperatures. EPR studies of PSII upon continuous illumination at 225 K with 0.7 mM of redox-active herbicide, Fe-III-(EDTA) linked by an ethane spacer to a dimethylphenyl urea group (2), produced a stable two-step S-1 to S-3 advance of the O-2-evolving complex (OEC) and a stoichiometric reduction of the Fe-III-(EDTA) moiety of the herbicide, while a control sample with 0.02 InM DCMU [3-(3,4-dichlorophenyl)-1,1-dimethyl-urea] and 0.7 mM of 4 exhibited only a one-step SI to St advance of the OEC without significant reduction of the Fe-III-(EDTA) moiety of the herbicide. Similar EPR results were obtained for 7, Fe-III-(EDTA) linked Ca the dimethylphenylurea group by a pentane spacer. O-2-evolution inhibition studies show that appending the Fe-III-(EDTA) moiety to the phenylurea herbicide causes a significant decrease in the binding affinity compared to that of DCMU. On the basis of O-2-evolution studies with various herbicide derivatives and different PSII sample types, the observed decrease in binding affinities is attributed to the degree of accessibility of the Q(B)-binding pocket to the herbicides and to electrostatic and hydrophilicity factors. The present study describes the use of novel metal-containing herbicides in studying long-range electron transfer in PSII and in trapping photogenerated two-electron oxidized intermediate states of the O-2-evolving complex.