p-nitrobenzyl ferulate | 138610-53-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: p-nitrobenzyl ferulate
• 英文别名: (4-Nitrophenyl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• CAS: 138610-53-4
• 化学式: C₁₇H₁₅NO₆
• 分子量: 329.309
• InChiKey: UBBKUQLROSLPTQ-UHFFFAOYSA-N

物化性质

• 沸点：
  523.1±45.0 °C(Predicted)
• 密度：
  1.342±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  阿魏酸 、 对硝基溴化苄 在 5,11,17,23,29,35-hexa-p-tert-butyl-37,38,39,40,41,42-hexakis(3,6,9-trioxadecyloxy)calix<6>arene 氢氧化钾 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 8.0h， 以88%的产率得到p-nitrobenzyl ferulate
  参考文献：
  名称：

  Catalytic ability of a flexible octopus-type calix[6]arene in ester-forming reactions and its structural properties

  摘要：

  The ester-forming reaction of alkali metal carboxylates with alkyl halides was catalyzed by the octopus-type calix[6]arene 1 which bears six 3,6,9-trioxadecyl substituents at the phenolic oxygens. The catalytic ability of 1 was significantly large in CH2Cl2 and CH3CN but negligible in less polar solvents such as benzene and dioxane. The catalytic ability is also affected by the amount of water present in the reaction system. A similar solvent effect was found in the alkali metal cation extraction by 1 from aqueous solutions to organic solvents. The conformation and structural mobility of 1 in organic solvents were studied by H-1 NMR spectroscopy at varying temperatures. Compound 1 had a 1,4-anti conformation (see Figure 4) both in CD2Cl2 and C6D6, but the orientation of the substituents on the aromatic rings of 1 varied with temperature. The reactivity features of 1 are discussed on the basis of its structural properties.

  DOI：

  10.1021/jo00069a039

文献信息

• Catalytic Ability of Octopus-Type Calixarene in the Formation of Esters from Alkyl Halides and Alkali Metal Carboxylates
  作者：Eisaku Nomura、Hisaji Taniguchi、Kouichi Kawaguchi、Yoshio Otsuji

  DOI：10.1246/cl.1991.2167

  日期：1991.12

  5,11,17,23,29,35-Hexa-p-tert-butyl-37,38,39,40,41,42-hexakis(3,6,9-trioxadecyloxy)calix[6]arene efficiently catatalyzes the reaction of alkyl halides with alkali metal carboxylates to produce esters.

  5,11,17,23,29,35-Hexa-p-tert-butyl-37,38,39,40,41,42-hexakis(3,6,9-trioxadecyloxy) 杯[6]芳烃有效催化卤代烷与碱金属羧酸盐反应生成酯。
• Catalytic ability of a flexible octopus-type calix[6]arene in ester-forming reactions and its structural properties
  作者：Eisaku Nomura、Hisaji Taniguchi、Kouichi Kawaguchi、Yoshio Otsuji

  DOI：10.1021/jo00069a039

  日期：1993.8

  The ester-forming reaction of alkali metal carboxylates with alkyl halides was catalyzed by the octopus-type calix[6]arene 1 which bears six 3,6,9-trioxadecyl substituents at the phenolic oxygens. The catalytic ability of 1 was significantly large in CH2Cl2 and CH3CN but negligible in less polar solvents such as benzene and dioxane. The catalytic ability is also affected by the amount of water present in the reaction system. A similar solvent effect was found in the alkali metal cation extraction by 1 from aqueous solutions to organic solvents. The conformation and structural mobility of 1 in organic solvents were studied by H-1 NMR spectroscopy at varying temperatures. Compound 1 had a 1,4-anti conformation (see Figure 4) both in CD2Cl2 and C6D6, but the orientation of the substituents on the aromatic rings of 1 varied with temperature. The reactivity features of 1 are discussed on the basis of its structural properties.