(2-Bromomethyl-phenyl)-carbamic acid allyl ester | 345201-69-6

• 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-Bromomethyl-phenyl)-carbamic acid allyl ester
• CAS: 345201-69-6
• 化学式: C₁₁H₁₂BrNO₂
• 分子量: 270.126
• InChiKey: NBUBDZSDEXKVRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2-Bromomethyl-phenyl)-carbamic acid allyl ester 在 lithium hydroxide 、 四(三苯基膦)钯 、 三正丁基氢锡 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 2-[[2-[[2-[[2-(5-Methyl-2,4-dioxopyrimidin-1-yl)acetyl]-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]amino]acetyl]amino]phenyl]methyl-[2-[2-oxo-4-(phenylmethoxycarbonylamino)pyrimidin-1-yl]acetyl]amino]acetic acid
  参考文献：
  名称：

  Backbone Modifications of Aromatic Peptide Nucleic Acid (APNA) Monomers and Their Hybridization Properties with DNA and RNA

  摘要：

  Aromatic peptide nucleic acid (APNA) monomers containing N-(2-aminobenzyl)-glycine, N-(2-aminobenzyl)-(R)- or -(S)-alanine, and N-(2-aminobenzyl)-beta -alanine moieties as part of their backbone were synthesized. These novel analogues were incorporated as a single "point mutation" in PNA hexamers, and their physicochemical properties were investigated by UV thermal denaturation and CD experiments. Destabilization in tripler formation between the PNA-APNA chimeras and complementary DNA or RNA oligomers was observed, as compared to the PNA control. The APNA monomer composed of the N-(2-aminobenzyl)-glycine backbone led to the smallest decrease in the thermal stability of the triplexes formed with DNA and RNA, while maintaining selectivity for base-pairing recognition. Since the PNA-APNA chimeras are more lipophilic than the corresponding PNA homopolymers, these oligomers may also exhibit better cell membrane permeability properties.

  DOI：

  10.1021/jo001650o
• 作为产物：
  描述：

  (2-hydroxymethylphenyl)carbamic acid allyl ester 在 四溴化碳 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以58%的产率得到(2-Bromomethyl-phenyl)-carbamic acid allyl ester
  参考文献：
  名称：

  Backbone Modifications of Aromatic Peptide Nucleic Acid (APNA) Monomers and Their Hybridization Properties with DNA and RNA

  摘要：

  Aromatic peptide nucleic acid (APNA) monomers containing N-(2-aminobenzyl)-glycine, N-(2-aminobenzyl)-(R)- or -(S)-alanine, and N-(2-aminobenzyl)-beta -alanine moieties as part of their backbone were synthesized. These novel analogues were incorporated as a single "point mutation" in PNA hexamers, and their physicochemical properties were investigated by UV thermal denaturation and CD experiments. Destabilization in tripler formation between the PNA-APNA chimeras and complementary DNA or RNA oligomers was observed, as compared to the PNA control. The APNA monomer composed of the N-(2-aminobenzyl)-glycine backbone led to the smallest decrease in the thermal stability of the triplexes formed with DNA and RNA, while maintaining selectivity for base-pairing recognition. Since the PNA-APNA chimeras are more lipophilic than the corresponding PNA homopolymers, these oligomers may also exhibit better cell membrane permeability properties.

  DOI：

  10.1021/jo001650o