[(2-fluoro-5-nitrophenyl)methyl]prop-2-enylamine | 278594-24-4

• 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-fluoro-5-nitrophenyl)methyl]prop-2-enylamine
• 英文别名: N-[(2-fluoro-5-nitrophenyl)methyl]prop-2-en-1-amine
• CAS: 278594-24-4
• 化学式: C₁₀H₁₁FN₂O₂
• 分子量: 210.208
• InChiKey: DLFAFWSPQRZVJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(2-fluoro-5-nitrophenyl)methyl]prop-2-enylamine 在 铁粉 、 氯化铵 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 10.0h， 生成 (2S)-7-amino-2-methyl-1-propan-2-yl-4-prop-2-enyl-2,5-dihydro-1,4-benzodiazepin-3-one
  参考文献：
  名称：

  A simple route to tetrahydro-1,4-benzodiazepin-3-ones bearing diverse N1, N4, and C10 functionalization

  摘要：

  We describe an efficient synthesis of enantiopure tetrahydro-1,4-benzodiazepine-3-ones derived from L-alanine. Diverse substitution at N1, N4, and C10 can be achieved by coupling various N-alkyl derivatives Of L-alanine and N-allyl-(2-fluoro-5nitro)benzylamine. Cyclization of this intermediate proceeds in high yield and without racernization, providing diversity at N1. The NO2 group was easily transformed into other functional groups or removed, providing diversity at C10. Finally, oxidative deallylation allows diverse substitution to be installed at N4. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.171
• 作为产物：
  描述：

  2-氟-5-硝基甲苯 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 反应 34.0h， 生成 [(2-fluoro-5-nitrophenyl)methyl]prop-2-enylamine
  参考文献：
  名称：

  A simple route to tetrahydro-1,4-benzodiazepin-3-ones bearing diverse N1, N4, and C10 functionalization

  摘要：

  We describe an efficient synthesis of enantiopure tetrahydro-1,4-benzodiazepine-3-ones derived from L-alanine. Diverse substitution at N1, N4, and C10 can be achieved by coupling various N-alkyl derivatives Of L-alanine and N-allyl-(2-fluoro-5nitro)benzylamine. Cyclization of this intermediate proceeds in high yield and without racernization, providing diversity at N1. The NO2 group was easily transformed into other functional groups or removed, providing diversity at C10. Finally, oxidative deallylation allows diverse substitution to be installed at N4. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.171

文献信息

• Novel and Highly Efficient Synthesis of Substituted Dibenz[b,g]1,5-oxazocines. A Direct Comparison of the Solution versus Solid-Phase Approach
  作者：Xiaohu Ouyang、Zhidong Chen、Longbin Liu、Celia Dominguez、Alexander S. Kiselyov

  DOI：10.1016/s0040-4020(00)00120-4

  日期：2000.4

  We describe a novel and highly efficient synthesis of substituted dibenz[b,g]1,5-oxazocines. The procedure is based on the SNAr of fluoride with the phenolic hydroxide of the properly assembled acyclic intermediate. A direct comparison of the solution-phase vs the solid-phase synthesis has been conducted. The speed of the synthesis, the purity of the desired eight-membered heterocycles (>95%), as well

  我们描述了一种新型的和高效的取代苯并[ b，g ] 1,5-恶唑啉合成。该程序基于氟化物的S N Ar与正确组装的无环中间体的酚式氢氧化物。进行了固相合成和固相合成的直接比较。合成速度，所需八元杂环的纯度（> 95％）以及所得文库的多样性是固相方法的绝对优势。通过固相方法合成的二苯并[ b，g ] 1,5-恶唑啉的产率通常更好，而通过两种方法合成的产物的纯度相同。