1-乙酰基-1,4-二氢-4-甲基吡啶-3-羧酸乙酯 | 350032-40-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 1-乙酰基-1,4-二氢-4-甲基吡啶-3-羧酸乙酯
• 英文名称: ethyl 1-acetyl-1,4-dihydro-4-methylpyridine-3-carboxylate
• 英文别名: Ethyl 1-acetyl-4-methyl-1,4-dihydropyridine-3-carboxylate；ethyl 1-acetyl-4-methyl-4H-pyridine-3-carboxylate
• CAS: 350032-40-5
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: RAIOAGRBFVJGKT-UHFFFAOYSA-N

物化性质

• 沸点：
  322.2±42.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-乙酰基-1,4-二氢-4-甲基吡啶-3-羧酸乙酯 在 manganese(IV) oxide 作用下， 以 甲苯 为溶剂， 反应 72.0h， 以88%的产率得到4-甲基烟酸乙酯
  参考文献：
  名称：

  Regioselective Formation of Novel Functionalized 1-Aza-9-oxafluorenes

  摘要：

  A small series of novel 1-aza-9-oxafluorenes have been prepared by regioselective cycloaddition reaction of p-benzoquinone to the sterically unhindered side of unsymmetrically substituted N-acyl-l,4-dihydropyridines (1). The stereochemistry of the products is discussed on the basis of X-Ray crystal structure analysis of one starting structure (la). The formation of pyridine derivatives by possible redox reaction of the adducts was not observed. Rotameric properties of the N-acyl-1,4-dihydropyridines are demonstrated by H-1 and C-13 NMR spectroscopy, thus stabilizing the 1,4-dihydropyridine system towards competing oxidation by the quinone.

  DOI：

  10.3987/com-00-9141
• 作为产物：
  描述：

  烟酸乙酯 在 copper(l) iodide 作用下， 以 四氢呋喃 为溶剂， 生成 1-乙酰基-1,4-二氢-4-甲基吡啶-3-羧酸乙酯
  参考文献：
  名称：

  Synthesis and first biological evaluation of 1-aza-9-oxafluorenes as novel lead structures for the development of small-sized cytostatics

  摘要：

  A first series of novel 1-aza-9-oxafluorenes has been prepared from 3-carbonyl substituted 1,4-dihydropyridines and p-benzoquinone as small-sized cytostatics. Biological evaluation has been carried out in various cancer cell-lines. First structure-activity relationships proved the 4-phenyl substituent to be more favorable than the 4-methyl substituent. Cytostatic properties are discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00769-7

文献信息

• Evaluation of the First Cytostatically Active 1-Aza-9-oxafluorenes as Novel Selective CDK1 Inhibitors with P-Glycoprotein Modulating Properties
  作者：Kristin Brachwitz、Burkhardt Voigt、Laurent Meijer、Olivier Lozach、Christoph Schächtele、Josef Molnár、Andreas Hilgeroth

  DOI：10.1021/jm021090g

  日期：2003.2.1

  The first series of synthetic 1-aza-9-oxafluorenes with cytostatic activities in the micromolar range was evaluated as cyclin-dependent kinase (CDK1) inhibitors. Activity was found to be selective in comparison to the inhibition of other kinases within the CDK family. Compounds were shown to inhibit the membrane-efflux pump P-glycoprotein responsible for multidrug resistance in cancer cells. First structure-activity relationships are discussed.
• Regioselective Formation of Novel Functionalized 1-Aza-9-oxafluorenes
  作者：Andreas Hilgeroth、Kristin Brachwitz、Ute Baumeister

  DOI：10.3987/com-00-9141

  日期：——

  A small series of novel 1-aza-9-oxafluorenes have been prepared by regioselective cycloaddition reaction of p-benzoquinone to the sterically unhindered side of unsymmetrically substituted N-acyl-l,4-dihydropyridines (1). The stereochemistry of the products is discussed on the basis of X-Ray crystal structure analysis of one starting structure (la). The formation of pyridine derivatives by possible redox reaction of the adducts was not observed. Rotameric properties of the N-acyl-1,4-dihydropyridines are demonstrated by H-1 and C-13 NMR spectroscopy, thus stabilizing the 1,4-dihydropyridine system towards competing oxidation by the quinone.
• Synthesis and first biological evaluation of 1-aza-9-oxafluorenes as novel lead structures for the development of small-sized cytostatics
  作者：Kristin Brachwitz、Andreas Hilgeroth

  DOI：10.1016/s0960-894x(01)00769-7

  日期：2002.2

  A first series of novel 1-aza-9-oxafluorenes has been prepared from 3-carbonyl substituted 1,4-dihydropyridines and p-benzoquinone as small-sized cytostatics. Biological evaluation has been carried out in various cancer cell-lines. First structure-activity relationships proved the 4-phenyl substituent to be more favorable than the 4-methyl substituent. Cytostatic properties are discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.