Methyl 4-(2-methyl-3-oxoprop-1-en-1-yl)benzoate | 103764-24-5

• 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: Methyl 4-(2-methyl-3-oxoprop-1-en-1-yl)benzoate
• 英文别名: methyl 4-(2-methyl-3-oxoprop-1-enyl)benzoate
• CAS: 103764-24-5
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: LYBXCKFUYKCZAC-UHFFFAOYSA-N

物化性质

• 沸点：
  347.1±25.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 4-(2-methyl-3-oxoprop-1-en-1-yl)benzoate 在 palladium on activated charcoal sodium tetrahydroborate 、 氢气 作用下， 以 甲醇 为溶剂， 反应 52.0h， 生成 甲基4-(3-羟基-2-甲基丙基)苯甲酸酯
  参考文献：
  名称：

  A chemo-enzymatic approach to optically active 3-(4-methoxycarbonyl)phenyl-2-methyl-1-propanols

  摘要：

  With a view to obtaining both enantiomers of 3-(4-methoxycarbonyl)phenyl-2-methyl-1-propanols, (R)-1 and (S)-1, from the respective racemate, (+/-)-1, the hydrolysis of its acetate, (+/-)-2, in the presence of porcine pancreatic lipase (PPL) has been studied. The optical puriry of (R)-1 and (S)-1 thus obtained was unsatisfactory (ee 22-27 %), and could not be increased beyond ee 33 % by repeated enzymatic hydrolysis of the unconverted fraction of the acetate. In contrast with this, the biohydrogenation of 3-(4-methoxycarbonyl)phenyl-2-methyl-2-propen-1-ol (4) with fermenting Saccharomyces cerevisiae afforded (S)-1 of considerably higher optical purity (ee 41-90 %, depending on the strain). The stereochemical correlation of the products obtained in the two biochemical processes under study shows that the PPL-catalyzed hydrolysis of (+/-)-2 produces preferably (R)-1.

  DOI：

  10.1007/bf00698514

文献信息

• Annulation of 2<i>H</i>-Pyran onto 1-Oxa- or 1-Azacyclohexane-2,4-diones and Their Analogues via Sequential Condensation with α-Substituted Enals and 6π-Electrocyclization
  作者：Md. Imran Hossain、Elkhabiry Shaban、Taku Ikemi、Wei Peng、Hiroyuki Kawafuchi、Tsutomu Inokuchi

  DOI：10.1246/bcsj.20130069

  日期：2013.7.15

  2H-Pyrans are constructed on a 1-oxa- or 1-azacyclohexane-2,4-dione core via Knoevenagel condensation with enals followed by 6π-electrocyclization, which are readily catalyzed with ethylenediammonium diacetate. This formal [3 + 3] strategy constitutes C–O and C–C bond making and the diastereomer formation is circumvented using 6,6-disubstitution with the same aryl group in the 1-oxacyclohexane-2,4-diones. This facile methodology significantly advances the access to polysubstituted bicyclic 2H-pyrans with a versatile substrate choice and improved stability of the product.

  通过Knoevenagel缩合反应与烯醛反应，随后进行6π-电环化反应，以1-氧杂-或1-氮杂环己烷-2,4-二酮为核心构建了2H-吡喃衍生物，这些反应易于用乙二胺二乙酸盐催化。这种形式上的[3 + 3]策略构成了C–O和C–C键的形成，并通过在1-氧杂环己烷-2,4-二酮中使用相同的芳基进行6,6-二取代来避免立体异构体的形成。这种简便的方法学极大地促进了多取代双环2H-吡喃的合成，具有多样化的底物选择和产品稳定性的提高。
• Design, synthesis, and in vitro cancer cell growth inhibition evaluation and antimalarial testing of trioxanes installed in cyclic 2-enoate substructures
  作者：Md. Imran Hossain、Marta Świtalska、Wei Peng、Mariko Takashima、Ning Wang、Marcel Kaiser、Joanna Wietrzyk、Shingo Dan、Takao Yamori、Tsutomu Inokuchi

  DOI：10.1016/j.ejmech.2013.08.008

  日期：2013.11

  A novel series of 1,2,4-trioxanes were synthesized from 2H-pyrans via photooxidation, and their antiproliferative and growth factor inhibitory activity has been investigated across a variety of human cancer cell lines. Compounds 5k, 51, 5s, 7a and 7c exhibited the highest activity and selectivity against a human leukemia (MV4-11) cell line (IC50 = 0.5 mu M). Compound 5o showed the highest growth factor inhibitory activity against a melanoma (LOX-IMVI) cancer cell line (GI(50) = 1.0 mu M). A SAR study has confirmed the importance of the 1,2,4-trioxane unit as a pharmacophore for anticancer activity. The computer-assisted database analysis, COMPARE, has suggested that the compounds have unique mechanisms of actions that were different from those of known anticancer drugs. Some of the selected trioxanes were tested against the NF54 strain, albeit showing weak antiplasmodial activity. The molecular docking of trioxanes and hemin reveals that a short distance (130 angstrom) leads to their physical contact. The UV-vis spectroscopic analysis ensured the definite complexation between 1,2,4-trioxanes and hemin. The role of hemin-trioxane interaction in the hemin-induced oxidative damage has been studied using methylene blue as a substrate by UV-vis spectroscopy. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Microwave-Irradiated Synthesis of 1,2-Dihydropyridines from N-Functionalized Enaminones and Enals through Domino Condensation and 6π-Azaelectrocyclization
  作者：Tsutomu Inokuchi、Elkhabiry Shaban、Md. Imran Hossain、Ming-Yu Wu、Yoshihiko Takemasa、Sachie Nagae、Wei Peng、Hiroyuki Kawafuchi

  DOI：10.3987/com-13-12844

  日期：——

  N-Amino-substituted 1,2-dihydropyridine motifs are constructed using cyclohexane-1,3-diones via the Knoevenagel condensation with enals followed by 6 pi-electrocyclization using ethylenediammonium diacetate as a catalyst under MW irradiation. A survey of substituents on the N atom of the enaminones indicated that the phenylamino and benzoylamino groups are favorable for the reaction, while phenyl, benzyl, and no-substituent are not. The substituent at C2 of enals is crucial for smooth formation of the corresponding adducts and slightly higher yields are obtained with enals bearing an electron-withdrawing aromatic at C3.
• A chemo-enzymatic approach to optically active 3-(4-methoxycarbonyl)phenyl-2-methyl-1-propanols
  作者：G. D. Gamalevich、A. V. Ignatenko、E. P. Serebryakov、N. E. Voishvillo

  DOI：10.1007/bf00698514

  日期：1995.4

  With a view to obtaining both enantiomers of 3-(4-methoxycarbonyl)phenyl-2-methyl-1-propanols, (R)-1 and (S)-1, from the respective racemate, (+/-)-1, the hydrolysis of its acetate, (+/-)-2, in the presence of porcine pancreatic lipase (PPL) has been studied. The optical puriry of (R)-1 and (S)-1 thus obtained was unsatisfactory (ee 22-27 %), and could not be increased beyond ee 33 % by repeated enzymatic hydrolysis of the unconverted fraction of the acetate. In contrast with this, the biohydrogenation of 3-(4-methoxycarbonyl)phenyl-2-methyl-2-propen-1-ol (4) with fermenting Saccharomyces cerevisiae afforded (S)-1 of considerably higher optical purity (ee 41-90 %, depending on the strain). The stereochemical correlation of the products obtained in the two biochemical processes under study shows that the PPL-catalyzed hydrolysis of (+/-)-2 produces preferably (R)-1.