methyl 2-(4-allyl-2-methoxyphenoxy)acetate | 113695-07-1

• 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 2-(4-allyl-2-methoxyphenoxy)acetate
• 英文别名: Acetic acid, [2-methoxy-4-(2-propenyl)phenoxy]-, methyl ester；methyl 2-(2-methoxy-4-prop-2-enylphenoxy)acetate
• CAS: 113695-07-1
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: JHZRWFXBGVCRJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-(4-allyl-2-methoxyphenoxy)acetate 在 sulfur 作用下， 反应 2.0h， 以31.42%的产率得到methyl 2-[2-methoxy-4-(3-thioxo-3H-1,2-dithiol-5-yl)phenoxy]acetate
  参考文献：
  名称：

  Controlled release of hydrogen sulfide significantly reduces ROS stress and increases dopamine levels in transgenic C. elegans

  摘要：

  已经开发出一种新型的肽基系统，它展示出缓慢和持续的H₂S释放，从而减少过氧化氢诱导的氧化应激，并增加转基因C. elegans模型中的多巴胺水平。

  DOI：

  10.1039/c9cc05153h
• 作为产物：
  描述：

  丁香酚 、 溴乙酸甲酯 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以46.33%的产率得到methyl 2-(4-allyl-2-methoxyphenoxy)acetate
  参考文献：
  名称：

  Controlled release of hydrogen sulfide significantly reduces ROS stress and increases dopamine levels in transgenic C. elegans

  摘要：

  已经开发出一种新型的肽基系统，它展示出缓慢和持续的H₂S释放，从而减少过氧化氢诱导的氧化应激，并增加转基因C. elegans模型中的多巴胺水平。

  DOI：

  10.1039/c9cc05153h

文献信息

• Synthesis and Hypolipidaemic Evaluation of a Series of α-Asarone Analogues Related to Clofibrate in Mice
  作者：Fernando Labarrios、Leticia Garduño、Maria Del Rosario Vidal、Raul Garcia、Maria Salazar、Elizdath Martinez、Francisco Diaz、German Chamorro、Joaquin Tamariz

  DOI：10.1211/0022357991772015

  日期：2010.2.18

  A series of α-asarone analogues related to clofibrate, containing an acetic acid group at C-2 of the aromatic ring, has been prepared as the acids or as the ethyl and methyl esters. The corresponding alcohols were also synthesized by reduction of the ethyl esters. The compounds were examined in hyperlipidaemic male mice to evaluate their ability to modify serum lipoprotein cholesterol, low-density lipoprotein cholesterol, high-density lipoprotein cholesterol and triglycerides after oral administration of 40 and 80 mg kg−1 for 6 days.

  Except for methyl 2-methoxy-5-nitro-4-(2-propenyl)phenoxyacetate at either dose, these clofibrate-related phenoxyacetic acid derivatives were found to have significant hypocholesterolaemic activity. Levels of low-density lipoprotein cholesterol and triglycerides were significantly reduced and those of high-density lipoprotein cholesterol were elevated. 2-Methoxy-5-nitro-4-(2-propenyl)phenoxyacetic acid was active at both doses in all the tests. Clofibrate (150 mg kg−1) was more potent at reducing low-density lipoprotein cholesterol. No activity was detected for the alcohol derivatives.

  These preliminary results suggest that this class of compound might have more promise as potential hypolipidaemic agents than other α-asarone derivatives. Further investigation and characterization should be performed to determine the mode of action of these agents on lipid metabolism.

  摘要：已制备了一系列与氯贝特相关的α-阿沙酮类似物，含有芳香环的C-2处的乙酸基团，作为酸或作为乙酸乙酯和甲酯。相应的醇也通过还原乙酸酯合成。这些化合物在高脂血症雄性小鼠中进行了检验，评估它们在口服40和80毫克/千克剂量下6天后对血清脂蛋白胆固醇、低密度脂蛋白胆固醇、高密度脂蛋白胆固醇和甘油三酯的调节能力。 除了在任何剂量下甲基2-甲氧基-5-硝基-4-(2-丙烯基)苯氧基乙酸酯外，这些与氯贝特相关的苯氧基乙酸衍生物被发现具有显著的降胆固醇活性。低密度脂蛋白胆固醇和甘油三酯水平显著降低，而高密度脂蛋白胆固醇升高。2-甲氧基-5-硝基-4-(2-丙烯基)苯氧基乙酸在所有测试中在两个剂量下均活跃。氯贝特（150毫克/千克）在降低低密度脂蛋白胆固醇方面更为有效。醇衍生物未检测到活性。 这些初步结果表明，这类化合物可能比其他α-阿沙酮衍生物更有潜力作为潜在的降脂药物。应进行进一步的研究和表征，以确定这些药物对脂质代谢的作用方式。
• Reaction of adamantan-2-amine and (adamantan-1-yl)methylamine with methyl 2-(4-allyl-2-methoxyphenoxy)acetate
  作者：I. A. Novakov、A. S. Yablokov、A. A. Vernigora、B. S. Orlinson、M. B. Navrotskii、S. N. Voloboev

  DOI：10.1007/s11172-017-1929-y

  日期：2017.9

  A reaction of methyl 2-(4-allyl-2-methoxyphenoxy)acetate with adamantan-2-amine and (adamantan-1-yl)methylamine in butanol leads, together with the target amides, to the formation of butyl ester of the corresponding acid, which is resistant to aminolysis.

  2-(4-烯丙基-2-甲氧基苯氧基)乙酸甲酯与金刚烷-2-胺和(金刚烷-1-基)甲胺在丁醇中的反应与目标酰胺一起形成相应的丁酯酸，耐氨解。
• [EN] NEW ANTICANCER COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS ANTICANCERS
  申请人：SULFIDRIS S R L

  公开号：WO2009065926A3

  公开（公告）日：2009-07-30
• Clauser, Monatshefte fur Chemie, 1901, vol. 22, p. 131
  作者：Clauser

  DOI：——

  日期：——
• Lozac'h; Mollier, Bulletin de la Societe Chimique de France, 1950, p. 1243
  作者：Lozac'h、Mollier

  DOI：——

  日期：——