3,3-bis(4-hydroxy-3-methylphenyl)pentanedioic acid diethyl ester | 151101-34-7

• 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: 3,3-bis(4-hydroxy-3-methylphenyl)pentanedioic acid diethyl ester
• 英文别名: diethyl 3,3-bis(4-hydroxy-3-methylphenyl)pentanedioate
• CAS: 151101-34-7
• 化学式: C₂₃H₂₈O₆
• 分子量: 400.472
• InChiKey: QGLCBEHPCIKTOO-UHFFFAOYSA-N

物化性质

• 沸点：
  550.1±45.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.91
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  93.06
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3,3-bis(4-hydroxy-3-methylphenyl)pentanedioic acid diethyl ester 在 potassium carbonate 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 5,14,20,29,32,37-hexamethyl-7,12,22,27-tetraoxapentacyclo<26.2.2.23,6.213,16.218,21>octatriaconta-3,5,13,15,18,20,28,30,31,33,35,37-dodecaene-2,2,17,17-tetraacetic acid tetraethyl ester
  参考文献：
  名称：

  催化环烷VII。双咪唑基-环烷的酯酶活性

  摘要：

  我们报告了具有两个咪唑残基的新型四氧杂[6.1.6.1]对环环烷3的合成，该残基连接到形成大环腔的两个二苯甲烷间隔基之一的苯环上。四个乙酸残基与两个间隔单元的中心碳原子分开，并确保3在水和二元水性溶剂混合物中的溶解度。环戊烷3在含水磷酸盐缓冲液（pH 8）中与乙酸硝基萘酯形成化学计量的包合物，并在周转条件下催化结合的底物的水解。

  DOI：

  10.1002/recl.19931120605
• 作为产物：
  描述：

  邻甲酚 、 1,3-丙酮二羧酸二乙酯 在 盐酸 作用下， 以 乙硫醇 为溶剂， 以77%的产率得到3,3-bis(4-hydroxy-3-methylphenyl)pentanedioic acid diethyl ester
  参考文献：
  名称：

  催化环烷VII。双咪唑基-环烷的酯酶活性

  摘要：

  我们报告了具有两个咪唑残基的新型四氧杂[6.1.6.1]对环环烷3的合成，该残基连接到形成大环腔的两个二苯甲烷间隔基之一的苯环上。四个乙酸残基与两个间隔单元的中心碳原子分开，并确保3在水和二元水性溶剂混合物中的溶解度。环戊烷3在含水磷酸盐缓冲液（pH 8）中与乙酸硝基萘酯形成化学计量的包合物，并在周转条件下催化结合的底物的水解。

  DOI：

  10.1002/recl.19931120605

文献信息

• Catalytic Dendrophanes as Enzyme Mimics: Synthesis, Binding Properties, Micropolarity Effect, and Catalytic Activity of Dendritic Thiazolio-cyclophanes
  作者：Tilo Habicher、François Diederich、Volker Gramlich

  DOI：10.1002/(sici)1522-2675(19990707)82:7<1066::aid-hlca1066>3.0.co;2-o

  日期：1999.7.7

  Catalytic dendrophanes 9 and 10 were prepared as functional mimics of the thiamine-diphosphate-dependent enzyme pyruvate oxidase, and studied as catalysts in the oxidation of naphthalene-2-carbaldehyde (4) to methyl naphthalene-2-carboxylate (8) (Scheme 1). They are composed of a thiazolio-cyclophane initiator core with four generation-2 (G-2) poly(etheramide) dendrons attached. The two dendrophanes were synthesized by a convergent growth strategy by coupling dendrons 11 and 12, respectively (Scheme 2), with (chloromethyl)-cyclophane 42 (Scheme 5) and subsequent conversion with 4-methylthiaaole (Scheme 7). The X-ray crystal structures of cyclophane precursors 30 (Scheme 3), 37 and 38 (Scheme 5) on the way to dendrophanes were determined (Fig. I). The crystal-structure analysis of the benzene clathrate of 37 revealed the formation of channel-like stacks by the cyclophane which incorporate its morpholinomethyl side chain and the enclathrated benzene molecule (Fig. 2). The interactions of the enclathrated benzene molecule with the phenyl rings of the two adjacent cyclophane molecules in the stack closely resemble those between neighboring benzene molecules in crystalline benzene (Fig. 3). The characterization by MALDI-TOF-MS (Fig. 4) and H-1- and C-13-NMR spectroscopy (Fig. 5) proved the monodispersity of the G-2 dendrophanes 9 and 10 with molecular weights up to 11500 Da (Eor 10). H-1-NMR and fluorescence binding titrations in H2O and aqueous MeOH showed that 9 and 10 form stable 1:1 complexes with naphthalene-2-carbaldehyde (4) and 6-(p-toluidino)naphthalene-2-sulfonate (48, TNS) (Tables 1 and 2). The evaluation of the fluorescence-emission maxima of bound TNS revealed that the dendritic branching creates a microenvironment of distinctly reduced polarity at the cyclophane core by limiting its exposure to bulk solvent. Initial rate studies for the oxidation of naphthalene-2-carbaldehyde to methyl naphthalene-2-carboxylate in basic aqueous MeOH in the presence of flavin derivative 6 revealed only a weak catalytic activity of dendrophanes 9 and 10 (Table 3), despite the favorable micropolarity at the cyclophane active site. The low catalytic activity in the interior of the macromolecules was explained by steric hindrance of reaction transition states by the dendritic branches.