methyl 2-(3-methoxybenzylidene)-3-oxobutanoate | 92565-02-1

• 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: methyl 2-(3-methoxybenzylidene)-3-oxobutanoate
• 英文别名: Methyl 2-[(3-methoxyphenyl)methylidene]-3-oxobutanoate
• CAS: 92565-02-1
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: MZYAXBKFZROFPX-UHFFFAOYSA-N

物化性质

• 沸点：
  356.4±27.0 °C(Predicted)
• 密度：
  1.146±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  methyl 2-(3-methoxybenzylidene)-3-oxobutanoate 在 吡啶 、 palladium 10% on activated carbon 、 氢气 、 三溴化硼 、 铜 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0~140.0 ℃ 、137.9 kPa 条件下， 反应 69.0h， 生成 methyl 2-{3-[(1-methyl-1H-benzimidazol-2-yl)oxy]benzyl}-3-oxobutanoate
  参考文献：
  名称：

  Design and Synthesis of Benzimidazole-Linked meta-Substituted Benzylidenes/Benzyls as Biologically Significant New Chemical Entities

  摘要：

  meta-Linked thiazolidinedione (TZD) and diethyl malonate (DEM)based benzylidenes and methyl acetoacetate (MAA)based benzyl moieties linked to the 2-position of N-methyl benzimidazole were synthesized. TZD- and DEM-based compounds were synthesized by condensation of 2,4-thiazolidinedone and DEM respectively with the corresponding 3-substituted benzaldehyde, whereas MAA-based compounds were obtained by halogen displacement with the corresponding 3-substituted phenol. These new chemical entities were designed to provide a balanced agonism at the peroxisome proliferator activated receptor alpha/gamma (PPAR/) in the management of type 2 diabetes: a move from glitazones to selective PPAR modulators (SPPARMs). Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2012.678461
• 作为产物：
  描述：

  乙酰乙酸甲酯 、 3-甲氧基苯甲醛 生成 methyl 2-(3-methoxybenzylidene)-3-oxobutanoate
  参考文献：
  名称：

  Fossheim, R.; Joslyn, A.; Solo, A. J., Journal of Medicinal Chemistry, 1988, vol. 31, # 2, p. 301 - 305

  摘要：

  DOI：

文献信息

• Fossheim, R.; Joslyn, A.; Solo, A. J., Journal of Medicinal Chemistry, 1988, vol. 31, # 2, p. 301 - 305
  作者：Fossheim, R.、Joslyn, A.、Solo, A. J.、Luchowski, E.、Rutledge, A.、Triggle, D. J.

  DOI：——

  日期：——
• Sequential acetalization-pyrolysis of .alpha.-acetylcinnamates and .alpha.-acetylbenzalacetones. A method for the generation of 2-carbonyl-substituted naphthalenes
  作者：Joseph R. Zoeller、Charles E. Sumner

  DOI：10.1021/jo00288a054

  日期：1990.1
• Design and Synthesis of Benzimidazole-Linked <i>meta</i>-Substituted Benzylidenes/Benzyls as Biologically Significant New Chemical Entities
  作者：Raman K. Verma、Rajiv Mall、Prithwish Ghosh、Vijay Kumar

  DOI：10.1080/00397911.2012.678461

  日期：2013.7.18

  meta-Linked thiazolidinedione (TZD) and diethyl malonate (DEM)based benzylidenes and methyl acetoacetate (MAA)based benzyl moieties linked to the 2-position of N-methyl benzimidazole were synthesized. TZD- and DEM-based compounds were synthesized by condensation of 2,4-thiazolidinedone and DEM respectively with the corresponding 3-substituted benzaldehyde, whereas MAA-based compounds were obtained by halogen displacement with the corresponding 3-substituted phenol. These new chemical entities were designed to provide a balanced agonism at the peroxisome proliferator activated receptor alpha/gamma (PPAR/) in the management of type 2 diabetes: a move from glitazones to selective PPAR modulators (SPPARMs). Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.