(4-甲酰基-2-甲氧基苯基)戊酸酯 | 125261-96-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 中文名称: (4-甲酰基-2-甲氧基苯基)戊酸酯
• 英文名称: Pentanoic acid, 4-formyl-2-methoxyphenyl ester
• 英文别名: (4-formyl-2-methoxyphenyl) pentanoate
• CAS: 125261-96-3
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: HJTALWDAUWWRBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-二氨基甲苯 、 (4-甲酰基-2-甲氧基苯基)戊酸酯 在 sodium hydrogensulfite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以73%的产率得到2-(4-valeroyloxy-3-methoxyphenyl)-5-methyl-1H-benzimidazole
  参考文献：
  名称：

  Synthesis of 2-[3-alkoxy-4-(hydroxy, alkoxy, acyloxy)phenyl]-5-methyl-1H-benzimidazoles

  摘要：

  From substituted benzaldehydes of the vanillin series and 4-methyl-1,2-phenylene diaminein the presence of sodium hydrogen sulfite in DMF medium at 80A degrees C new functionally substituted 2-[3-alkoxy-4-(hydroxy, alkoxy, acyloxy)phenyl]-5-methyl-1H-benzimidazoles were obtained in preparative yields.

  DOI：

  10.1134/s1070428011050071
• 作为产物：
  描述：

  香草醛 、 戊酰氯 以 苯 为溶剂， 反应 1.0h， 生成 (4-甲酰基-2-甲氧基苯基)戊酸酯
  参考文献：
  名称：

  Vanilline Alkanoates in the Synthesis of Hexahydrobenzacridine and Octahydroxanthene Derivatives

  摘要：

  1,3-环己二酮与二甲基双酮在2-萘胺和香草醛酯的作用下，发生级联杂环化反应，生成了2-甲氧基-4-(烷基-11-氧代-7,8,9,10,11,12-六氢苯并[a]吖啶-12-基)和2-甲氧基-4-(烷基-1,8-二氧代-2,3,4,5,6,7,8,9-八氢-1H-咕吨-9-基)苯酯的脂肪族(C1-C4)羧酸衍生物。

  DOI：

  10.1007/s11176-005-0282-2

文献信息

• Vanilline Alkanoates in the Synthesis of Hexahydrobenzacridine and Octahydroxanthene Derivatives
  作者：N. G. Kozlov、L. I. Basalaeva

  DOI：10.1007/s11176-005-0282-2

  日期：2005.4

  Cascade heterocyclization of 1,3-cyclohexanedione and dimedone with 2-naphthylamine and vanilline esters gave derivatives of 2-methoxy-4-(alkyl-11-oxo-7,8,9,10,11,12-hexahydrobenz[a]acridin-12-yl)- and 2-methoxy-4-(alkyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl esters of aliphatic (C1– C4 ) carboxylic acids.

  1,3-环己二酮与二甲基双酮在2-萘胺和香草醛酯的作用下，发生级联杂环化反应，生成了2-甲氧基-4-(烷基-11-氧代-7,8,9,10,11,12-六氢苯并[a]吖啶-12-基)和2-甲氧基-4-(烷基-1,8-二氧代-2,3,4,5,6,7,8,9-八氢-1H-咕吨-9-基)苯酯的脂肪族(C1-C4)羧酸衍生物。
• Preparative Synthesis of Vanillin and Vanillal Alkanoates
  作者：E. A. Dikusar、O. G. Vyglazov、K. L. Moiseichuk、N. A. Zhukovskaya、N. G. Kozlov

  DOI：10.1007/s11167-005-0242-y

  日期：2005.1

  Procedures for preparing vanillin and vanillal alkanoates were developed.

  制备香草醛及其烷酸酯的工艺流程被开发出来。
• Synthesis and Ligand Based 3D-QSAR of 2,3-Bis-benzylidenesuccinaldehyde Derivatives as New Class Potent FPTase Inhibitor, and Prediction of Active Molecules
  作者：Min-Gyu Soung、Jong-Han Kim、Byoung-Mog Kwon、Nack-Do Sung

  DOI：10.5012/bkcs.2010.31.5.1355

  日期：2010.5.20

  In order to search new inhibitors against farnesyl protein transferase (FPTase), a series of 2,3-bis-benzylidenesuccinaldehyde derivatives (1-29) were synthesized and their inhibition activities ($pI_50}$) against FPTase were measured. From based on the reported results that the inhibitory activities of dimers 2,3-bis-benzylidenesuccinaldehydes were higher than those of monomers cinnamaldehydes, 3D-QSARs on FPTase inhibitory activities of the dimers (1-29) were studied quantitatively using comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) methods. The statistical qualities of the optimized CoMFA model II ($r^2_cv.}}$= 0.693 and $r^2_ncv.}}$= 0.974) was higher than those of the CoMSIA model II ($r^2_cv.}}$ = 0.484 and $r^2_ncv.}}$ = 0.928). The dependence of CoMFA models on chance correlations was evaluated with progressive scrambling analyses. And the inhibitory activity exhibited a strong correlation with steric factors of the substrate molecules. Therefore, from the results of graphical analyses on the contour maps and of predicted higher inhibitory active compounds, it is suggested that the structural distinctions and descriptors that contribute to inhibitory activities ($pI_50}$) against FPTase will be able to applied new inhibitor design.

  为寻找针对法尼酰蛋白转移酶（FPTase）的新抑制剂，合成了一系列2,3-双苄叉琥珀醛衍生物（1-29），并测量了它们对FPTase的抑制活性（$pI_50}$）。基于以前的报道，2,3-双苄叉琥珀醛二聚体的抑制活性高于单体肉桂醛，因此采用比较分子场分析（CoMFA）和比较分子相似性指数分析（CoMSIA）方法，对二聚体（1-29）的FPTase抑制活性进行了定量研究。优化后的CoMFA模型II的统计质量（$r^2_cv.}}$= 0.693和$r^2_ncv.}}$= 0.974）高于CoMSIA模型II（$r^2_cv.}}$= 0.484和$r^2_ncv.}}$= 0.928）。通过逐步打乱分析评估了CoMFA模型对偶然相关性的依赖。抑制活性与底物分子的立体因素表现出强相关性。因此，基于轮廓图的图形分析结果和预测的高抑制活性化合物，建议在针对FPTase的抑制活性（$pI_50}$）的结构特征和描述符方面的差异，可以应用于新抑制剂的设计。
• Synthesis of aromatic azomethines by condensation of substituted benzaldehydes with 4-aminophenylene-N-imide of maleopimaric acid
  作者：E. A. Dikusar、M. P. Bei、A. P. Yuvchenko、V. I. Potkin

  DOI：10.1134/s1070363210070170

  日期：2010.7

  Preparative method of synthesis of aromatic azomethines by condensation of substituted benzaldehydes of vanillin series with 4-aminophenylene-N-imide of maleopimaric acid was developed.

  研制了香兰素系列取代苯甲醛与马来酸4-氨基亚苯基-N-酰亚胺缩合合成芳族甲亚胺的制备方法。
• Synthesis of azomethines by condensation of substituted benzaldehydes with 3-aminophenylen-N-imide of maleopimaric acid
  作者：M. P. Bey、A. P. Yuvchenko、E. A. Dikusar、V. I. Potkin

  DOI：10.1134/s1070363211030200

  日期：2011.3

  New method for the synthesis of azomethines by condensation of substituted benzaldehydes of the vanillin series with 3-aminophenylen-N-imide of maleopimaric acid is developed.

  提出了将香兰素系列取代苯甲醛与马来酸3-氨基苯甲基-N-酰亚胺缩合合成偶氮甲碱的新方法。