1-benzyl-3-(4-methoxybenzyl)urea | 188911-54-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-benzyl-3-(4-methoxybenzyl)urea
• 英文别名: N-Benzyl-N'-(4-methoxybenzyl)urea；1-benzyl-3-[(4-methoxyphenyl)methyl]urea
• CAS: 188911-54-8
• 化学式: C₁₆H₁₈N₂O₂
• mdl: MFCD15674490
• 分子量: 270.331
• InChiKey: ZTKPCNPGXYPVPM-UHFFFAOYSA-N

物化性质

• 沸点：
  510.0±43.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)
• 保留指数：
  2680.5

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.187
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苄脲 在 titanium(IV) isopropylate 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 28.0h， 生成 1-benzyl-3-(4-methoxybenzyl)urea
  参考文献：
  名称：

  异丙醇钛（IV）和硼氢化钠的新型合成二取代脲

  摘要：

  本文介绍了异丙醇钛（IV）/硼氢化钠介导的芳香醛与单取代脲的酰胺化还原反应，高产率制备不对称二取代脲的方法。

  DOI：

  10.1016/s0040-4039(97)00149-4

文献信息

• Kinetics and Mechanism of the Aminolysis of Aryl N-Benzyl Thiocarbamates in Acetonitrile
  作者：Hyuck-Keun Oh

  DOI：10.5012/bkcs.2011.32.1.137

  日期：2011.1.20

  The aminolysis reactions of phenyl N-benzyl thiocarbamate with benzylamines in acetonitrile at $50.0^\circ}C$ are investigated. The reactions are first order in both the amine and the substrate. Under amine excess, pseudo-first coefficient ($k_obs}$) are obtained, plot of $k_obs}$ vs free amine concentration are linear. The signs of $\rho}_XZ}$ (< 0) are consistent with concerted mechanism. Moreover, the variations of $\rho_X$ and $\rho_Z$ with respect to the sustituent in the substrate and large $\rho}_XZ}$ value indicate that the reactions proceed concerted mechanism. The normal kinetic isotope effects ($k_H/k_D$ = 1.3 ~ 1.5) involving deuterated benzylamine nucleophiles suggest a hydrogen-bonded, four-centered-type transition state. The activation parameters, $\Delta}H^\ddagger$ and $\Delta}S^\ddagger$, are consistent with this transition state structure.

  对苯基 N-苄基硫代氨基甲酸酯与苄胺在乙腈中50.0°C下的氨解反应进行了研究。反应对胺和底物均为一级。在胺过量情况下，获得了伪一级速率常数（$k_obs}$），$k_obs}$ 与游离胺浓度的关系图为线性。参量 $\rho_XZ}$（< 0）的符号与协同机理一致。此外，$\rho_X$ 和 $\rho_Z$ 随底物取代基的变化以及较大的 $\rho_XZ}$ 值表明反应通过协同机理进行。正常的动力学同位素效应（$k_H/k_D$ = 1.3 ~ 1.5）涉及氘代苄胺亲核试剂，表明过渡态为氢键作用的四中心类型。活化参数 $\Delta H^\ddagger$ 和 $\Delta S^\ddagger$ 与此过渡态结构相符。
• [EN] METHODS AND COMPOSITIONS FOR SELECTIVE AND TARGETED CANCER THERAPY<br/>[FR] PROCÉDÉS ET COMPOSITIONS POUR UNE CANCÉROTHÉRAPIE SÉLECTIVE ET CIBLÉE
  申请人：UNIV TEXAS

  公开号：WO2015035051A1

  公开（公告）日：2015-03-12

  Provided herein are methods and compositions for selective and targeted cancer therapy, in particular certain benzothiophenes, benzothiazoles, oxalamides, N-acyl ureas and chromones, and their use in selectively treating certain adenocarcinomas. In some embodiments, the selective toxicity of the compounds may be mediated through SCD1 and/or CYP450 such as CYP4F11.

  本文提供了用于选择性和靶向癌症治疗的方法和组合物，特别是某些苯并噻吩、苯并噻唑、草酰胺、N-酰基脲和色酮，以及它们在选择性治疗某些腺癌中的应用。在某些实施例中，这些化合物的选择性毒性可能通过SCD1和/或CYP450（如CYP4F11）介导。
• Ruthenium-Catalyzed Urea Synthesis Using Methanol as the C1 Source
  作者：Seung Hyo Kim、Soon Hyeok Hong

  DOI：10.1021/acs.orglett.5b03328

  日期：2016.1.15

  An unprecedented protocol for urea synthesis directly from methanol and amine was accomplished. The reaction is highly atom-economical, producing hydrogen as the sole byproduct. Commercially available ruthenium pincer complexes were used as catalysts. In addition, no additive, such as a base, oxidant, or hydrogen acceptor, was required. Furthermore, unsymmetrical urea derivatives were successfully

  直接从甲醇和胺合成尿素的空前方案已经完成。该反应是高度原子经济的，产生氢作为唯一的副产物。使用可商购的钌夹钳配合物作为催化剂。另外，不需要添加剂，例如碱，氧化剂或氢受体。此外，通过一锅两步反应成功获得了不对称脲衍生物。
• Self-indicating amine scavenger resins
  作者：Jin Ku Cho、Peter D. White、Wolfgang Klute、Tony W. Dean、Mark Bradley

  DOI：10.1039/b315426b

  日期：——

  Self-indicating methylisocyanate resin, which functions as both a scavenger and an indicator for amines, was used for in-situ reaction monitoring and purification of a urea based library.

  自指示性甲基异氰酸酯树脂既作为胺的捕捉剂又作为指示剂，用于尿素基库的原位反应监测和纯化。
• Potent Natural Soluble Epoxide Hydrolase Inhibitors from Pentadiplandra brazzeana Baillon: Synthesis, Quantification, and Measurement of Biological Activities In Vitro and In Vivo
  作者：Seiya Kitamura、Christophe Morisseau、Bora Inceoglu、Shizuo G. Kamita、Gina R. De Nicola、Maximilienne Nyegue、Bruce D. Hammock

  DOI：10.1371/journal.pone.0117438

  日期：——

  We describe here three urea-based soluble epoxide hydrolase (sEH) inhibitors from the root of the plant Pentadiplandra brazzeana. The concentration of these ureas in the root was quantified by LC-MS/MS, showing that 1, 3-bis (4-methoxybenzyl) urea (MMU) is the most abundant (42.3 μg/g dry root weight). All of the ureas were chemically synthesized, and their inhibitory activity toward recombinant human and recombinant rat sEH was measured. The most potent compound, MMU, showed an IC50 of 92 nM via fluorescent assay and a Ki of 54 nM via radioactivity-based assay on human sEH. MMU effectively reduced inflammatory pain in a rat nociceptive pain assay. These compounds are among the most potent sEH inhibitors derived from natural sources. Moreover, inhibition of sEH by these compounds may mechanistically explain some of the therapeutic effects of P. brazzeana.

  我们在这里描述了三种来自植物 Pentadiplandra brazzeana 根部的基于尿素的可溶性环氧化物水解酶 (sEH) 抑制剂。通过 LC-MS/MS 对根中这些尿素的浓度进行定量，结果表明 1, 3-双（4-甲氧基苄基）尿素 (MMU) 含量最丰富（42.3 μg/g 根干重）。所有尿素都是化学合成的，并测量了它们对重组人和重组大鼠 sEH 的抑制活性。最有效的化合物 MMU 通过荧光测定显示的 IC50 为 92 nM，通过基于放射性的测定对人 sEH 显示的 Ki 为 54 nM。在大鼠伤害性疼痛测定中，MMU 有效减轻炎性疼痛。这些化合物是源自天然来源的最有效的 sEH 抑制剂。此外，这些化合物对 sEH 的抑制可以从机制上解释 P. brazzeana 的一些治疗作用。