N-(4-fluorobenzyl)pyrimidin-2-amine | 458-74-2

• 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: N-(4-fluorobenzyl)pyrimidin-2-amine
• 英文别名: (4-fluoro-benzyl)-pyrimidin-2-yl-amine；(4-Fluor-benzyl)-pyrimidin-2-yl-amin；N-[(4-fluorophenyl)methyl]pyrimidin-2-amine
• CAS: 458-74-2
• 化学式: C₁₁H₁₀FN₃
• mdl: MFCD00453601
• 分子量: 203.219
• InChiKey: ZJTVSAZKNICZGE-UHFFFAOYSA-N

物化性质

• 沸点：
  367.7±44.0 °C(Predicted)
• 密度：
  1.268±0.06 g/cm3(Predicted)
• 熔点：
  91-92 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  37.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-fluorobenzyl)pyrimidin-2-amine 、 2-溴-3-苯基丙醛 在 一水合肼 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以29%的产率得到4-benzyl-1-(4-fluorobenzyl)-1H-imidazol-2-amine
  参考文献：
  名称：

  A small chemical library of 2-aminoimidazole derivatives as BACE-1 inhibitors: Structure-based design, synthesis, and biological evaluation

  摘要：

  In this work, we report a rational structure-based approach aimed at the discovery of new 2-aminoimidazoles as beta-secretase inhibitors. Taking advantage of a microwave-assisted synthetic protocol, a small library of derivatives was obtained and biologically evaluated. Two compounds showed promising activities in both enzymatic and cellular assays. Moreover, one of them exhibited the capability to cross the blood brain barrier as assessed by the parallel artificial membrane permeability assay. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.12.016
• 作为产物：
  描述：

  [1-(4-Fluoro-phenyl)-meth-(Z)-ylidene]-pyrimidin-2-yl-amine 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以60%的产率得到N-(4-fluorobenzyl)pyrimidin-2-amine
  参考文献：
  名称：

  Research on antibacterial and antifungal agents. XI. Synthesis and antimicrobial activity of N-heteroaryl benzylamines and their Schiff bases

  摘要：

  The synthesis and antimicrobial activity of new N-heteroaryl benzylamines and their Schiff bases are reported. Antifungal data were compared with those obtained with miconazole ketoconazole, enilconazole and imazalil sulfate; which showed that some of the tested compounds possessed moderate activity against strains of Candida albicans, Candida sp and good activity against isolates of plant pathogenic fungi, In contrast the synthesized compounds showed poor antibacterial activity, except for 3j which exhibited a better activity than nalidixic acid used as positive control. The results obtained are discussed on the basis of structure-activity relationships.

  DOI：

  10.1016/0223-5234(96)88217-1

文献信息

• Tandem Hydrogen‐Borrowing Dehydrogenative Coupling and Hydrodefluorination
  作者：Baldeep K. Sidhu、Rajarshi Mondal、David E. Herbert

  DOI：10.1002/adsc.202301383

  日期：2024.4.23

  use of a catalyst and a thermodynamic sink, such as formation of a strong Si−F bond.4 Numerous systems capable of HDF have been reported,5 including transition metal complexes,6-8 main-group compounds,9-12 and light-driven processes.13-15 A problem that can arise is that the bond dissociation enthalpy of a C−F bond decreases as the number of fluorine atoms around the carbon is reduced, making it easier

  介绍 作为氢的等排体，氟的策略性包含可以改变化合物的化学性质，而不影响分子大小或结构。1, 2虽然 CF 3单元的掺入已被广泛接受，但由于这种独特的化学单元带来的合成挑战，带有 CF 2 H 基团的分子相对较少。 3为了获得 CF 2 H 部分，可以通过单个 CF 键的加氢脱氟 (HDF) 来修饰三氟甲基。然而，CF 键的动力学惰性和强度使该过程具有挑战性，通常需要使用催化剂和热力学汇，例如形成强 Si−F 键。4已报道了许多能够进行 HDF 的系统，5包括过渡金属配合物、6-8 种主族化合物、9-12和光驱动过程。13-15可能出现的一个问题是，随着碳周围氟原子数量的减少，CF 键的键解离焓降低，使得 CF 2 H 基团中的 C−F 键更容易断裂。在CF 3中。因此，CF 3基团的HDF常常导致完全脱氟而不是取代单个氟。3另一个问题是外部氢源。通常，使用添加剂例如硅烷或H 2 。由于硅烷
• Saijo, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1952, vol. 72, p. 1447,1450
  作者：Saijo

  DOI：——

  日期：——