ethyl 3-methoxy-3-phenylacrylate | 7759-03-7

• 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: ethyl 3-methoxy-3-phenylacrylate
• 英文别名: Ethyl 3-methoxy-3-phenylprop-2-enoate
• CAS: 7759-03-7
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: ROFWCAULVGPCLM-UHFFFAOYSA-N

物化性质

• 沸点：
  78-82 °C(Press: 0.1 Torr)
• 密度：
  1.067±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 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：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-methoxy-3-phenylacrylate 在 氢氧化钾 作用下， 生成 3-methoxy-3-phenylpropenic acid
  参考文献：
  名称：

  Condensation of carboxylic esters with ethyl ethynyl ether

  摘要：

  DOI：

  10.1007/bf00854867
• 作为产物：
  描述：

  苯甲酰乙酸乙酯 、 三甲基硅烷化重氮甲烷 以 甲醇 、 正己烷 、 乙腈 为溶剂， 反应 36.0h， 以100%的产率得到ethyl 3-methoxy-3-phenylacrylate
  参考文献：
  名称：

  Structure–activity studies of a series of dipyrazolo[3,4- b :3′,4′- d ]pyridin-3-ones binding to the immune regulatory protein B7.1

  摘要：

  The interaction of co-stimulatory molecules on T cells with 137 molecules on antigen presenting cells plays an important role in the activation of naive T cells. Consequently, agents that disrupt these interactions should have applications in treatment of transplant rejection as well as autoimmune diseases. To this end, specific small molecule inhibitors of human B7.1 were identified and characterized. Herein, we report the identification of potent small molecule inhibitors of the B7.1-CD28 interaction. In a high-throughput screen we identified several leads that prevented the interaction of B7.1 with CD28 with activities in the nanomolar to low micromolar range. One of these, the dihydrodipyrazolopyridinone 1, was subsequently shown to bind the V-like domain of human B7.1 at equimolar stoichiometry. With this as a starting point, we report here the synthesis and initial in vitro structure-activity relationships of a series of these compounds. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00183-4

文献信息

• Access and Regioselective Transformations of 6-Substituted 4-Aryl-2,8-dichloropyrido[3,2-<i>d</i>]pyrimidine Compounds
  作者：Gwenaelle Bouscary-Desforges、Agnes Bombrun、John Kallikat Augustine、Gérald Bernardinelli、Anna Quattropani

  DOI：10.1021/jo300189q

  日期：2012.5.18

  toward SNAr reactions was investigated. Amination yielded high C-2 regioselectivity, while thiolation was influenced by C-6 substituents, resulting in medium to high C-2 versus C-8 regioselectivity. The last chloride was efficiently displaced by SNAr, Suzuki–Miyaura cross-coupling reaction, or reduction. C-2 arylation as a final step was also possible by Liebeskind–Srogl cross-coupling reaction on the

  我们在此报告了一种在C-6上带有R 1取代基的2,4,8-三氯吡啶并[3,2- d ]嘧啶1的合成方法。这种支架的潜力通过区域选择性地取代每个芳族氯化物以引入多样性的可能性得到了证明。依次进行硫亲核加成，然后进行Liebeskind-Srogl交叉偶联反应，在三氯吡啶并[3,2- d ]嘧啶衍生物上的C-4处引入了前所未有的芳基引入。其余两种氯化物对S N的反应性差异研究了Ar反应。胺化产生高C-2区域选择性，而硫醇化则受C-6取代基影响，导致C-2相对于C-8区域选择性中等至较高。S N Ar，Suzuki-Miyaura交叉偶联反应或还原有效地置换了最后的氯化物。Liebeskind-Srogl对先前引入的C-2硫醚的交叉偶联反应也可能使C-2芳基化成为最后一步。简明和高度发散的合成使用的1被开发，从而提供一种有效的方法来探索吡啶并[3,2的结构-活性关系d ]嘧啶衍生物，例如9，10，15，和16。
• Synthesis of (Z)-N-hydroxy-3-methoxy-3-phenylacrylamide as new selective inhibitor of hepatitis C virus replication
  作者：M. V. Kozlov、A. A. Kleymenova、K. A. Konduktorov、A. Z. Malikova、K. A. Kamarova、R. A. Novikov、S. N. Kochetkov

  DOI：10.1134/s1068162016010076

  日期：2016.3

  hydroxamic acid (CHA) inhibits replication of hepatitis C virus (HCV). We synthesized a structural analogue of CHA, i.e., (Z)-N-hydroxy-3-methoxy3-phenylacrylamide, which inhibited HCV replication five times more selectively than CHA. It was found that both compounds did not inhibit deacetylation of Ac-α-tubulin with histone deacetylase 6, the activity of which is important for virus replication.

  根据最近公布的结果，肉桂异羟肟酸 (CHA) 抑制丙型肝炎病毒 (HCV) 的复制。我们合成了 CHA 的结构类似物，即 (Z)-N-羟基-3-甲氧基3-苯基丙烯酰胺，其抑制 HCV 复制的选择性是 CHA 的五倍。发现这两种化合物均不抑制 Ac-α-微管蛋白与组蛋白脱乙酰酶 6 的脱乙酰作用，组蛋白脱乙酰酶的活性对病毒复制很重要。
• Conditions for reactions mediated by yeast
  申请人：Victoria University

  公开号：US07723065B2

  公开（公告）日：2010-05-25

  Organic compounds, such as precursors for aryl ethylamines such as ephedrine, aryl propylamines such as fluoxetine and propionic acid derivatives such as ibuprofen, naproxen and fenoprofen, are subjected to a yeast mediated reduction conducted in the absence of a solvent. The yeast is moistened with water and contacted with the organic compound. The yeast may then be contacted with an organic solvent to dissolve the product of the reaction into the solvent, and a solid/liquid separation used to separate the product from the yeast.

  有机化合物，例如苯乙胺的前体如麻黄碱，苯丙胺如氟西汀和丙酸衍生物如布洛芬、萘普生和非洛酮，经过无溶剂的酵母介导还原。酵母用水湿润并与有机化合物接触。然后可以将酵母与有机溶剂接触，将反应产物溶解到溶剂中，并使用固液分离将产物与酵母分离。
• Discovery of a new class of cinnamyl-triazole as potent and selective inhibitors of aromatase (cytochrome P450 19A1)
  作者：James McNulty、Kunal Keskar、Denis J. Crankshaw、Alison C. Holloway

  DOI：10.1016/j.bmcl.2014.07.083

  日期：2014.9

  Synthesis of a novel class of natural product inspired cinnamyl-containing 1,4,5-triazole and the potent inhibition of human aromatase (CYP 450 19A1) by select members is described. Structure-activity data generated provides insights into the requirements for potency particularly the inclusion of an aryl bromide or chloride residue as a keto-bioisostere. (C) 2014 Elsevier Ltd. All rights reserved.
• Emelina, E. E.; Ershov, B. A., Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, # 4, p. 692 - 696
  作者：Emelina, E. E.、Ershov, B. A.

  DOI：——

  日期：——