2-[2-(2-methoxy-ethoxy)-ethoxy]-ethyl 3-amino-5-bromo-4-methyl-benzoate | 905712-42-7

• 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: 2-[2-(2-methoxy-ethoxy)-ethoxy]-ethyl 3-amino-5-bromo-4-methyl-benzoate
• CAS: 905712-42-7
• 化学式: C₁₅H₂₂BrNO₅
• 分子量: 376.247
• InChiKey: HEBHNKWCHSQNLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  22.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  80.01
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-[2-(2-methoxy-ethoxy)-ethoxy]-ethyl 3-amino-5-bromo-4-methyl-benzoate 在 亚硝酸特丁酯 、 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 以81%的产率得到
  参考文献：
  名称：

  Solid-Phase Synthesis of m-Phenylene Ethynylene Heterosequence Oligomers

  摘要：

  Both homo- and heterosequence m-phenylene ethynylene oligomers are synthesized using a conceptually simple iterative solid-phase strategy. Oligomers are attached to Merrifield's resin through a known triazene-type linkage. The phenylene ethynylene molecular backbone is constructed through a series of palladium-mediated cross-coupling reactions. The strategy employs two types of monomers that bear orthogonal reactivity, one being a monoprotected bisethynyl arene and the other being a 3-bromo-5-iodo arene. The catalyst conditions are tailored to the requirements of each monomer type. The monoprotected bisethynyl arene is coupled to the growing chain in 2 h at room temperature using a Pd(I) dimer precatalyst ((Bu3P)-Bu-t-(Pd(mu-Cl)(mu-2-methyl allyl) Pd)(PBu3)-Bu-t) in conjunction with ZnBr2 and diisopropylamine. In alternate steps, the resin is deprotected in situ with TBAF and coupled to the 3-bromo-5-iodo arene using the iodo selective Pd(tri-2-furylphosphine) 4 catalyst in conjunction with CuI and piperidine; this reaction is also completed in 2 h at room temperature. These cross-coupling events are alternated until an oligomer of the desired length is achieved. The oligomer is then cleaved from the resin using CH2I2/I-2 at 110 degrees C and purified using preparatory GPC. Using this method, a series of homo- and heterosequence oligomers up to 12 units in length in excellent yield and purity were synthesized on the 100 mg scale. Longer oligomers were attempted; however, deletion sequences were found in oligomers longer than 12 units.

  DOI：

  10.1021/jo0607212
• 作为产物：
  描述：

  三甘醇单甲醚 在 platinum on activated charcoal 甲酸 、 三乙胺 、 diphenylammonium triflate 作用下， 以 甲苯 为溶剂， 反应 21.0h， 生成 2-[2-(2-methoxy-ethoxy)-ethoxy]-ethyl 3-amino-5-bromo-4-methyl-benzoate
  参考文献：
  名称：

  Solid-Phase Synthesis of m-Phenylene Ethynylene Heterosequence Oligomers

  摘要：

  Both homo- and heterosequence m-phenylene ethynylene oligomers are synthesized using a conceptually simple iterative solid-phase strategy. Oligomers are attached to Merrifield's resin through a known triazene-type linkage. The phenylene ethynylene molecular backbone is constructed through a series of palladium-mediated cross-coupling reactions. The strategy employs two types of monomers that bear orthogonal reactivity, one being a monoprotected bisethynyl arene and the other being a 3-bromo-5-iodo arene. The catalyst conditions are tailored to the requirements of each monomer type. The monoprotected bisethynyl arene is coupled to the growing chain in 2 h at room temperature using a Pd(I) dimer precatalyst ((Bu3P)-Bu-t-(Pd(mu-Cl)(mu-2-methyl allyl) Pd)(PBu3)-Bu-t) in conjunction with ZnBr2 and diisopropylamine. In alternate steps, the resin is deprotected in situ with TBAF and coupled to the 3-bromo-5-iodo arene using the iodo selective Pd(tri-2-furylphosphine) 4 catalyst in conjunction with CuI and piperidine; this reaction is also completed in 2 h at room temperature. These cross-coupling events are alternated until an oligomer of the desired length is achieved. The oligomer is then cleaved from the resin using CH2I2/I-2 at 110 degrees C and purified using preparatory GPC. Using this method, a series of homo- and heterosequence oligomers up to 12 units in length in excellent yield and purity were synthesized on the 100 mg scale. Longer oligomers were attempted; however, deletion sequences were found in oligomers longer than 12 units.

  DOI：

  10.1021/jo0607212