methyl 4-hydroxy-2-methylene-3-phenylbutanoate | 204334-92-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 4-hydroxy-2-methylene-3-phenylbutanoate
• 英文别名: Methyl 2-(2-hydroxy-1-phenylethyl)acrylate；methyl 4-hydroxy-2-methylidene-3-phenylbutanoate
• CAS: 204334-92-9
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: YMVFERDGYXYMRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-hydroxy-2-methylene-3-phenylbutanoate 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到3-methylene-4-phenyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  β，γ-二芳基α-亚甲基-γ-丁内酯作为抗耐甲氧西林金黄色葡萄球菌的有效抗菌剂

  摘要：

  筛选了通过烯丙基硼化或烯丙基化反应合成的一系列外消旋α-亚甲基-γ-丁内酯（AMGBL），以抗耐甲氧西林的金黄色葡萄球菌（MRSA）美国300。与天然的AMGBLs（例如，单苯二酚）不同，在β和γ位置带有芳基的合成类似物对MRSA具有有效的作用。最有效的分子在最小抑制浓度（MIC）为3.0至5.2μM的情况下，可与万古霉素和利奈唑胺（最后一种针对MRSA感染的药物）媲美。这些内酯还显示出对其他临床上重要的耐多药革兰氏阳性细菌（肠球菌除外）有效的抗菌活性，同时还显示出对哺乳动物细胞的高度耐受性。在标准的时间杀灭动力学分析中，这些分子中的几个在快速杀死高MRSA接种物（2 h和12 h）方面超过了万古霉素，化合物为1l和1m在低浓度下，可显着降低MRSA的细胞内负担约98–99％。此外，该化合物在抑制葡萄球菌蛋白酶产生方面超过了万古霉素，表明合成的亚甲基内酯作为有希望的抗MRSA候选物值得进一步研究。

  DOI：

  10.1016/j.bioorg.2020.104183
• 作为产物：
  描述：

  2-(羟基苯基甲基)-丙烯酸甲酯 在 indium 、 N-溴代丁二酰亚胺(NBS) 、 二甲基硫 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 20.0h， 生成 methyl 4-hydroxy-2-methylene-3-phenylbutanoate
  参考文献：
  名称：

  Effective 1,4-Asymmetric C−C/C−O Stereoinduction in Indium-Promoted Coupling Reactions of Aldehydes to Protected and Unprotected [1-(Bromomethyl)vinyl] Alkanols. The Status of Intramolecular Chelation within Functionalized Allylindium Reagents

  摘要：

  The stereochemistry of the coupling reactions of oxygen-substituted bromides 8-10 with isobutyraldehyde, benzaldehyde, and cyclohexanecarboxaldehyde in water is described. The examples involving the O-silylated derivatives 8 exhibit moderate anti stereoselectivity. In contrast, rather high (most often in excess of 80:20) syn diastereofacial bias is observed when hydroxy bromides 10 are involved. Consequently, stereocontrolled 1,4-asymmetric induction under aqueous conditions can be realized in either direction on demand. These results are considered to reflect the fact that the siloxy systems enter into C-C bond formation via conventional Felkin-Anh transition state arrangements. The crossover observed for the unprotected analogues is believed to be a consequence of the preferred adoption of chelated transition states, these interactions likely being fundamental to aqueous organometallic chemistry.

  DOI：

  10.1021/jo9715534

文献信息

• [EN] STERICALLY HINDERED AMINE AND OXYALKYL AMINE LIGHT STABILIZERS<br/>[FR] AMINE STÉRIQUEMENT ENCOMBRÉE ET AGENTS DE STABILISATION À LA LUMIÈRE D'OXYALKYLAMINE
  申请人：3M INNOVATIVE PROPERTIES CO

  公开号：WO2016105990A1

  公开（公告）日：2016-06-30

  The present disclosure relates to sterically hindered alkyl amine and sterically hindered oxyalkyl amine compounds, as well as particles, substrates, coatings, and articles including the same.

  本公开涉及到受空间位阻限制的烷基胺和受空间位阻限制的氧烷基胺化合物，以及包含这些化合物的颗粒、基板、涂层和制品。
• [EN] STERICALLY HINDERED ALKYL AND OXYALKYL AMINE LIGHT STABILIZERS<br/>[FR] ALKYLE STÉRIQUEMENT ENCOMBRÉ ET AGENTS DE STABILISATION À LA LUMIÈRE D'OXYALKYLE
  申请人：3M INNOVATIVE PROPERTIES CO

  公开号：WO2016105993A1

  公开（公告）日：2016-06-30

  Compounds having hindered amine and oxyalkyl amine light stabilizers can mitigate the adverse effects of actinic radiation, such as visible and ultraviolet light, on polymers and copolymers. Polymers and copolymers derived from such compounds. Articles, such as coated articles and molded articles, containing such polymers or compounds.

  具有受阻胺和氧烷基胺光稳定剂的化合物可以减轻紫外光和可见光等光辐射对聚合物和共聚物的不良影响。从这些化合物衍生的聚合物和共聚物。包含这些聚合物或化合物的涂层制品和成型制品。
• Sterically hindered amine and oxyalkyl amine light stabilizers
  申请人：3M INNOVATIVE PROPERTIES COMPANY

  公开号：US10000626B2

  公开（公告）日：2018-06-19

  The present disclosure relates to sterically hindered alkyl amine and sterically hindered oxyalkyl amine compounds, as well as particles, substrates, coatings, and articles including the same.

  本公开涉及立体受阻烷基胺和立体受阻氧烷基胺化合物，以及包括这些化合物的颗粒、基材、涂层和物品。
• Factors influencing the cytotoxicity of α-methylene-γ-hydroxy esters against pancreatic cancer
  作者：P. Veeraraghavan Ramachandran、Matthew A. Helppi、Arlie L. Lehmkuhler、Jennifer M. Marchi、C. Max Schmidt、Michele T. Yip-Schneider

  DOI：10.1016/j.bmcl.2015.07.087

  日期：2015.10

  A systematic study to identify the factors influencing the cytotoxicity of a-methylene-c-hydroxy esters against three pancreatic cancer cell lines (Panc-1, MIA-PaCa-2, and BxPC-3) has established that, in addition to Michael acceptor abilities, the possibility to lactonize to alpha-methylene-gamma-butyrolactones is as important. The substitution pattern and the number of carbons between the hydroxy and ester moieties also influence the bio-activity. (C) 2015 Elsevier Ltd. All rights reserved.
• Moirangthem, Nimalini D.; Thingom, Bhavna; Laitonjam, Warjeet S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2009, vol. 48, # 3, p. 455 - 459
  作者：Moirangthem, Nimalini D.、Thingom, Bhavna、Laitonjam, Warjeet S.

  DOI：——

  日期：——