N-cyclohexyl-4-(3-propylthioureido)butyramide | 1431634-34-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-cyclohexyl-4-(3-propylthioureido)butyramide
• 英文别名: N-cyclohexyl-4-(propylcarbamothioylamino)butanamide
• CAS: 1431634-34-2
• 化学式: C₁₄H₂₇N₃OS
• 分子量: 285.454
• InChiKey: PTIQTYXMYSTONI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  85.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-cyclohexyl-4-(3-propylthioureido)butyramide 在 sodium hydroxide 、 双氧水 作用下， 以 水 为溶剂， 反应 0.17h， 以98%的产率得到N-cyclohexyl-4-(3-propylureido)butyramide
  参考文献：
  名称：

  Fragmentation reactions of thiourea- and urea-compounds examined by tandem MS-, energy-resolved CID experiments, and theory

  摘要：

  Fragmentation reactions of thiourea- and urea-compounds, which are promising reagents for chemical crosslinking (XL), are investigated in detail by collision-induced dissociation (CID) experiments in a quadrupole ion trap (QIT), energy-resolved CID experiments, and computational modeling. For this study, an array of six labeled and unsymmetrical substituted thiourea- and urea-derivatives were synthesized, which allow unambiguous characterization of competing fragmentation pathways. The results of the QIT-CID-experiments are explored in detail for two compounds and confirmed by results for the other four. These results document the subtle competition of characteristic fragmentation pathways of this class of compounds. The multi dimensional investigations of the characteristic fragmentation reactions allow reliable structure proposals of prominent productions. Energy-dependent CID experiments on two of the six compounds lead to breakdown curves that show similar relative threshold energies for the formation of the product ions on which the functioning of the XL application relies. The experimental results are in full consistency with the results from in-depth computations. For the dominant fragmentations observed, the transition states for moving the proton from the most basic site of the precursor ion (the thiourea-sulfur or the urea carbonyl oxygen) to less basic heteroatoms in the protonated molecular ion is the necessary and decisive step that determines the extent of the charge-driven fragmentation processes that follow. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ijms.2012.06.023
• 作为产物：
  描述：

  tert-butyl N-[4-(cyclohexylamino)-4-oxobutyl]carbamate 在 三乙胺 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 24.58h， 生成 N-cyclohexyl-4-(3-propylthioureido)butyramide
  参考文献：
  名称：

  Fragmentation reactions of thiourea- and urea-compounds examined by tandem MS-, energy-resolved CID experiments, and theory

  摘要：

  Fragmentation reactions of thiourea- and urea-compounds, which are promising reagents for chemical crosslinking (XL), are investigated in detail by collision-induced dissociation (CID) experiments in a quadrupole ion trap (QIT), energy-resolved CID experiments, and computational modeling. For this study, an array of six labeled and unsymmetrical substituted thiourea- and urea-derivatives were synthesized, which allow unambiguous characterization of competing fragmentation pathways. The results of the QIT-CID-experiments are explored in detail for two compounds and confirmed by results for the other four. These results document the subtle competition of characteristic fragmentation pathways of this class of compounds. The multi dimensional investigations of the characteristic fragmentation reactions allow reliable structure proposals of prominent productions. Energy-dependent CID experiments on two of the six compounds lead to breakdown curves that show similar relative threshold energies for the formation of the product ions on which the functioning of the XL application relies. The experimental results are in full consistency with the results from in-depth computations. For the dominant fragmentations observed, the transition states for moving the proton from the most basic site of the precursor ion (the thiourea-sulfur or the urea carbonyl oxygen) to less basic heteroatoms in the protonated molecular ion is the necessary and decisive step that determines the extent of the charge-driven fragmentation processes that follow. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ijms.2012.06.023

文献信息

• Fragmentation reactions of thiourea- and urea-compounds examined by tandem MS-, energy-resolved CID experiments, and theory
  作者：Francesco Falvo、Lukas Fiebig、Frank Dreiocker、Ran Wang、P.B. Armentrout、Mathias Schäfer

  DOI：10.1016/j.ijms.2012.06.023

  日期：2012.12

  Fragmentation reactions of thiourea- and urea-compounds, which are promising reagents for chemical crosslinking (XL), are investigated in detail by collision-induced dissociation (CID) experiments in a quadrupole ion trap (QIT), energy-resolved CID experiments, and computational modeling. For this study, an array of six labeled and unsymmetrical substituted thiourea- and urea-derivatives were synthesized, which allow unambiguous characterization of competing fragmentation pathways. The results of the QIT-CID-experiments are explored in detail for two compounds and confirmed by results for the other four. These results document the subtle competition of characteristic fragmentation pathways of this class of compounds. The multi dimensional investigations of the characteristic fragmentation reactions allow reliable structure proposals of prominent productions. Energy-dependent CID experiments on two of the six compounds lead to breakdown curves that show similar relative threshold energies for the formation of the product ions on which the functioning of the XL application relies. The experimental results are in full consistency with the results from in-depth computations. For the dominant fragmentations observed, the transition states for moving the proton from the most basic site of the precursor ion (the thiourea-sulfur or the urea carbonyl oxygen) to less basic heteroatoms in the protonated molecular ion is the necessary and decisive step that determines the extent of the charge-driven fragmentation processes that follow. (C) 2012 Elsevier B.V. All rights reserved.