(R)-(2-(4-nitrophenyl)-4,5-dihydrooxazol-5-yl)methanol | 1020192-49-7

• 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: (R)-(2-(4-nitrophenyl)-4,5-dihydrooxazol-5-yl)methanol
• 英文别名: (2-(4-nitrophenyl)-4,5-dihydrooxazol-5-yl)methanol；[(5R)-2-(4-nitrophenyl)-4,5-dihydro-1,3-oxazol-5-yl]methanol
• CAS: 1020192-49-7
• 化学式: C₁₀H₁₀N₂O₄
• 分子量: 222.2
• InChiKey: KGGNEPCUVUVVPG-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  87.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-(2-(4-nitrophenyl)-4,5-dihydrooxazol-5-yl)methanol 、 甲基磺酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 [(5R)-2-(4-nitrophenyl)-4,5-dihydro-1,3-oxazol-5-yl]methyl methanesulfonate
  参考文献：
  名称：

  Constrained Analogues of Procaine as Novel Small Molecule Inhibitors of DNA Methyltransferase-1

  摘要：

  Constrained analogues of procaine were synthesized, and their inhibiting activity against DNMT1 was tested. Among them, the most potent compound, derivative 3b, was also able to induce a recognizable demethylation of chromosomal satellite repeats in HL60 human myeloid leukemia cells and thus represents a lead compound for the development of a novel class of non-nucleoside DNMT1 inhibitors.

  DOI：

  10.1021/jm7015705
• 作为产物：
  描述：

  (R)-3-氨基-1,2-丙二醇 、 对硝基苯甲腈 在 zinc(II) chloride 作用下， 以 N-甲基吡咯烷酮 、 氯苯 为溶剂， 反应 24.0h， 以63%的产率得到(R)-(2-(4-nitrophenyl)-4,5-dihydrooxazol-5-yl)methanol
  参考文献：
  名称：

  Constrained Analogues of Procaine as Novel Small Molecule Inhibitors of DNA Methyltransferase-1

  摘要：

  Constrained analogues of procaine were synthesized, and their inhibiting activity against DNMT1 was tested. Among them, the most potent compound, derivative 3b, was also able to induce a recognizable demethylation of chromosomal satellite repeats in HL60 human myeloid leukemia cells and thus represents a lead compound for the development of a novel class of non-nucleoside DNMT1 inhibitors.

  DOI：

  10.1021/jm7015705

文献信息

• Stereoselective Oxidative Cyclization of <i>N</i>-Allyl Benzamides to Oxaz(ol)ines
  作者：Ayham H. Abazid、Tom-Niklas Hollwedel、Boris J. Nachtsheim

  DOI：10.1021/acs.orglett.1c01607

  日期：2021.7.2

  This study presents an enantioselective oxidative cyclization of N-allyl carboxamides via a chiral triazole-substituted iodoarene catalyst. The method allows the synthesis of highly enantioenriched oxazolines and oxazines, with yields of up to 94% and enantioselectivities of up to 98% ee. Quaternary stereocenters can be constructed and, besides N-allyl amides, the corresponding thioamides and imideamides

  本研究介绍了通过手性三唑取代的碘芳烃催化剂对N-烯丙基甲酰胺进行对映选择性氧化环化。该方法允许合成高度对映体富集的恶唑啉和恶嗪，产率高达 94%，对映选择性高达 98% ee。可以构建四元立体中心，除了N-烯丙基酰胺外，相应的硫代酰胺和酰亚胺酰胺作为底物也具有良好的耐受性，从而产生大量的手性 5 元N-杂环。通过应用大量进一步的功能化，我们最终证明了观察到的手性杂环作为合成其他对映体富集目标结构的战略中间体的高价值。
• Constrained Analogues of Procaine as Novel Small Molecule Inhibitors of DNA Methyltransferase-1
  作者：Sabrina Castellano、Dirk Kuck、Marina Sala、Ettore Novellino、Frank Lyko、Gianluca Sbardella

  DOI：10.1021/jm7015705

  日期：2008.4.1

  Constrained analogues of procaine were synthesized, and their inhibiting activity against DNMT1 was tested. Among them, the most potent compound, derivative 3b, was also able to induce a recognizable demethylation of chromosomal satellite repeats in HL60 human myeloid leukemia cells and thus represents a lead compound for the development of a novel class of non-nucleoside DNMT1 inhibitors.