2-[2-(2-methoxyethoxy)ethoxy]ethyl 3-bromo-5-nitrobenzoate | 398119-24-9

• 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-methoxyethoxy)ethoxy]ethyl 3-bromo-5-nitrobenzoate
• 英文别名: 2-[2-(2-methoxyethoxy)ethoxy]ethyl 5-bromo-3-nitrobenzoate；2-[2-(methoxyethoxy)ethoxy]ethyl 3-bromo-5-nitrobenzoate
• CAS: 398119-24-9
• 化学式: C₁₄H₁₈BrNO₇
• 分子量: 392.203
• InChiKey: RSMNMPFACZGRGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.19
• 重原子数：
  23.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  97.13
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-[2-(2-methoxyethoxy)ethoxy]ethyl 3-bromo-5-nitrobenzoate 在 platinum on activated charcoal 甲酸 、 三乙胺 作用下， 反应 5.0h， 以78%的产率得到2-[2-(2-methoxyethoxy)ethoxy]ethyl 5-bromo-3-aminobenzoate
  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 、 3-溴-5-硝基苯甲酸甲酯 在 potassium carbonate 作用下， 以78%的产率得到2-[2-(2-methoxyethoxy)ethoxy]ethyl 3-bromo-5-nitrobenzoate
  参考文献：
  名称：

  含亚胺的间亚苯基亚乙炔基大环的合成和自缔合。

  摘要：

  这项研究的目的是通过确定间苯撑乙炔基大环化合物1在溶液和固体中形成π堆积聚集体的能力，来测试亚胺键作为亚苯基乙炔撑大环化合物和低聚物骨架内结构单元的适用性。州。由二胺4和二醛5高收率合成具有两个亚胺键的大环1。形成亚胺的大环化步骤在各种条件下进行，仅通过将反应物在甲醇中回流即可获得最佳收率。通过（1）1 H NMR探测1在各种溶剂中的自缔合行为。丙酮-d（6）和四氢呋喃-d（8）中的缔合常数（K（E））通过使用不确定的自缔合模型拟合浓度依赖性化学位移确定。结果表明，在含亚胺的间亚苯基亚乙炔基大环中，可以保持溶剂化驱动的分子间pi-pi堆积。有趣的是，在丙酮中，大环化合物1表现出更强的形成二聚体的趋势，而不是更高的聚集体。我们假设这种行为可能是由于偶极亚胺基之间的静电吸引。通过广角和小角X射线粉末衍射（WAXD和SAXD）研究了1的固态堆积。1的布拉格反射与六角堆积图案相符，类似于我们先前对

  DOI：

  10.1021/jo010918o

文献信息

• The Size-Selective Synthesis of Folded Oligomers by Dynamic Templation
  作者：Tohru Nishinaga、Aya Tanatani、Keunchan Oh、Jeffrey S. Moore

  DOI：10.1021/ja025698q

  日期：2002.5.1

  A dynamic pool of m-phenylene ethynylene oligomers generated by sequence ligation using the imine metathesis reaction was equilibrated under a variety of conditions, and the mixture of products was analyzed by HPLC. The equilibration was performed in the presence and absence of rodlike ligand 2b, which exhibits an affinity for the helical oligomers that is very length specific. Among the eight oligomers generated during metathesis equilibrium, the formation of 22-mer 6b was enhanced in acetonitrile in the presence of 2b. This particular oligomer has the highest binding affinity for 2b. Quantitative analysis by HPLC of the products indicated that 6b was produced in 66% yield in the presence of 2 equiv 2b while a 37% yield was produced in the absence of 2b. Judging from the binding affinities of oligomers 6 with 2b, the equilibrium shifting was driven by the selective binding of 6b with 2b.
• Reversible Polymerization Driven by Folding
  作者：Dahui Zhao、Jeffrey S. Moore

  DOI：10.1021/ja026957e

  日期：2002.8.1

  Bisfunctionalized m-phenylene ethynylene imine oligomers were polymerized in the polar solvent acetonitrile, resulting in high-molecular weight poly(m-phenylene ethynylene imine)s. It is hypothesized that this polymerization, which proceeds through the reversible metathesis of imine bonds, is driven by the folding of the long m-phenylene ethynylene imine chains. Upon conducting the polymerization in a series of solvents in which the m-phenylene ethynylene oligomers exhibit different folding stabilities, it was possible to correlate the molecular weight of the resulting poly(m-phenylene ethynylene imine)s with the helical stability of the corresponding oligomers. The polymerization was also demonstrated to be reversible and responsive to solvent and temperature changes.