ethyl 3-(2-methoxyphenyl)-2-methylacrylate

• 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-(2-methoxyphenyl)-2-methylacrylate
• 英文别名: 3-(2-Methoxy-phenyl)-2-methyl-acrylic acid ethyl ester；ethyl (E)-3-(2-methoxyphenyl)-2-methylprop-2-enoate
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: OGVXTDLOMHOBKU-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  邻甲氧基苯甲醛 、 2-溴丙酸乙酯 在 potassium iodide (Ph₃O)3P 、 {C[CH₂(OCH₂CH₂)2Te(CHMeCO₂Et)(Bu)]4}⁽⁴⁺⁾*4Br^(1-) 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 以67%的产率得到ethyl 3-(2-methoxyphenyl)-2-methylacrylate
  参考文献：
  名称：

  季戊四醇衍生寡糖的合成，表征及其在维蒂希型催化反应中的应用

  摘要：

  几种具有游离羟基的季戊四醇衍生的低聚乙二醇1可以通过收敛方法容易地制备。定量13 C NMR被证明是表征低聚乙二醇的有效工具。合成了相应的低聚乙二醇17的碲化物，并将其用作Wittig型反应的良好催化剂，以高收率或高收率制备二取代和三取代的烯烃。

  DOI：

  10.1021/jo049701v

文献信息

• Nucleophilic Amination of Methoxy Arenes Promoted by a Sodium Hydride/Iodide Composite
  作者：Atsushi Kaga、Hirohito Hayashi、Hiroyuki Hakamata、Miku Oi、Masanobu Uchiyama、Ryo Takita、Shunsuke Chiba

  DOI：10.1002/anie.201705916

  日期：2017.9.18

  Come full circle: A method for the nucleophilic amination of methoxy arenes was established by using sodium hydride (NaH) in the presence of lithium iodide (LiI). This method offers an efficient route to benzannulated nitrogen heterocycles. Mechanistic studies showed that the reaction proceeds through an unusual concerted nucleophilic aromatic substitution.

  围成一圈：在碘化锂（LiI）存在下，使用氢化钠（NaH）建立了甲氧基芳烃的亲核胺化方法。该方法提供了一条有效的途径来制得二环氮杂环。机理研究表明，该反应通过异常的协同的亲核芳族取代进行。
• Stereoselective Olefination of N-Sulfonyl Imines with Stabilized Phosphonium Ylides for the Synthesis of Electron-Deficient Alkenes
  作者：Fan Fang、Yuan Li、Shi-Kai Tian

  DOI：10.1002/ejoc.201001379

  日期：2011.2

  alkenes in moderate to excellent yields from readily accessible N-sulfonyl imines and stabilized phosphonium ylides. Significantly, the olefination reaction of N-sulfonylimines with nitrile-stabilized phosphonium ylides affords an array of α,β-unsaturated nitriles with high Z selectivity, and the reactions with ester-, amide-, and ketone-stabilized phosphonium ylides afford α,β-unsaturated esters, amides

  已经开发了一种前所未有的方案，用于从易于获得的 N-磺酰基亚胺和稳定的鏻叶立德以中等至优异的产率立体选择性合成结构多样的缺电子烯烃。值得注意的是，N-磺酰亚胺与腈稳定的鏻叶立德的烯化反应提供了一系列具有高 Z 选择性的 α,β-不饱和腈，并且与酯、酰胺和酮稳定的鏻叶立德的反应提供了 α,β -分别具有高 E 选择性的不饱和酯、酰胺和酮。反应混合物的光谱分析和中间体的捕获允许提出合理的机制。初始亚胺/叶立德加成导致形成环化形成 1 的甜菜碱，2-氮杂膦烷随后消除亚氨基膦以产生烯烃。对于缺电子的 1,2-二取代烯烃的合成，甜菜碱中吸电子基团的存在允许通过质子转移在其两种非对映异构体之间快速相互转化。烯烃合成的 Z/E 选择性由两种甜菜碱非对映异构体形成相应的 1,2-氮杂膦非对映异构体的不同速率决定。相比之下，合成缺电子三取代烯烃的 Z/E 选择性源于稳定的鏻叶立德与 N-磺酰基亚胺的非对映选
• MACROCYCLIC GHRELIN RECEPTOR MODULATORS AND METHODS OF USING THE SAME
  申请人：Hoveyda Hamid

  公开号：US20080194672A1

  公开（公告）日：2008-08-14

  The present invention provides novel conformationally-defined macrocyclic compounds that can function as selective modulators of the ghrelin receptor (growth hormone secretagogue receptor, GHS-R1a and subtypes, isoforms and variants thereof). Methods of synthesizing the novel compounds are also described herein. These compounds are useful as agonists of the ghrelin receptor and as medicaments for treatment and prevention of a range of medical conditions including, but not limited to, metabolic and/or endocrine disorders, gastrointestinal disorders, cardiovascular disorders, obesity and obesity-associated disorders, central nervous system disorders, bone disorders, genetic disorders, hyperproliferative disorders and inflammatory disorders.

  本发明提供了一种新颖的构象定义明确的大环化合物，可以作为生长激素分泌素受体（GHS-R1a及其亚型、异构体和变体）的选择性调节剂。本文还描述了合成这些新型化合物的方法。这些化合物可用作生长激素分泌素受体的激动剂，用于治疗和预防一系列医疗状况，包括但不限于代谢和/或内分泌紊乱、胃肠道紊乱、心血管疾病、肥胖和与肥胖相关的疾病、中枢神经系统疾病、骨骼疾病、遗传疾病、过度增生性疾病和炎症性疾病。
• MACROCYCLIC ANTAGONISTS OF THE MOTILIN RECEPTOR FOR TREATMENT OF GASTROINTESTINAL DYSMOTILITY DISORDERS
  申请人：Marsault Eric

  公开号：US20100093720A1

  公开（公告）日：2010-04-15

  The present invention provides conformationally-defined macrocyclic compounds that bind to and/or are functional modulators of the motilin receptor including subtypes, isoforms and/or variants thereof. These macrocyclic compounds, at a minimum, possess adequate pharmacological properties to be useful as therapeutics for a range of disease indications. In particular, these compounds are useful for treatment and prevention of disorders characterized by hypermotilinemia and/or gastrointestinal hypermotility, including, but not limited to, diarrhea, cancer treatment-related diarrhea, cancer-induced diarrhea, chemotherapy-induced diarrhea, radiation enteritis, radiation-induced diarrhea, stress-induced diarrhea, chronic diarrhea, AIDS-related diarrhea, C. difficile associated diarrhea, traveller's diarrhea, diarrhea induced by graph versus host disease, other types of diarrhea, dyspepsia, irritable bowel syndrome, chemotherapy-induced nausea and vomiting (emesis) and post-operative nausea and vomiting and functional gastrointestinal disorders. In addition, the compounds possess utility for the treatment of diseases and disorders characterized by poor stomach or intestinal absorption, such as short bowel syndrome, celiac disease and cachexia. The compounds also have use for the treatment of inflammatory diseases and disorders of the gastrointestinal tract, such as inflammatory bowel disease, ulcerative colitis, Crohn's disease and pancreatitis. Accordingly, methods of treating such disorders and pharmaceutical compositions including compounds of the present invention are also provided.

  本发明提供了与胃动素受体及其亚型、异构体和/或变体结合和/或是功能调节剂的构象定义明确的大环化合物。这些大环化合物至少具有足够的药理特性，可用作治疗一系列疾病指示的治疗药物。特别是，这些化合物对于治疗和预防以高胃动素血症和/或胃肠道高蠕动性为特征的疾病非常有用，包括但不限于腹泻、癌症治疗相关腹泻、癌症诱导腹泻、化疗诱导腹泻、放射性肠炎、放射性腹泻、压力诱导腹泻、慢性腹泻、艾滋病相关腹泻、C. difficile相关腹泻、旅行者腹泻、移植物宿主病引起的腹泻、其他类型的腹泻、消化不良、肠易激综合征、化疗诱导的恶心和呕吐（呕吐）以及术后恶心和呕吐和功能性胃肠道疾病。此外，这些化合物对于治疗以胃或肠道吸收不良为特征的疾病和疾病也具有用途，例如短肠综合征、乳糜泻和虚弱。这些化合物还可用于治疗胃肠道炎症性疾病和疾病，如炎症性肠病、溃疡性结肠炎、克罗恩病和胰腺炎。因此，本发明还提供了治疗此类疾病的方法和包括本发明化合物的药物组合物。
• Highly <i>E</i>-Selective Solvent-Free Horner-Wadsworth-Emmons Reaction for the Synthesis of α-Methyl-α,β-Unsaturated Esters Using Either LiOH·H₂O or Ba(OH)₂·8H₂O
  作者：Kaori Ando、Wakana Isomura、Nariaki Uchida、Kanae Mori

  DOI：10.1246/bcsj.20220052

  日期：2022.6.15

  Horner-Wadsworth-Emmons reaction, which stirs a mixture of aldehyde, phosphonate reagent 1, and a base without solvent. The reaction of aromatic aldehydes and triethyl 2-phosphonopropionate 1a using LiOH·H2O gave 95-99% E-selectivity in 83-97% yield. The reaction of 1a with aliphatic aldehydes gave 92-94% E-selectivity except for α-branched aldehydes, and the selectivity was improved to 97-98% using ethyl 2-(diis

  ( E )-α-甲基-α,β-不饱和酯通过Horner-Wadsworth-Emmons 反应制备，该反应在无溶剂的情况下搅拌醛、膦酸酯试剂1和碱的混合物。芳香醛和 2-膦酰基丙酸三乙酯1a使用 LiOH·H 2 O 反应得到 95-99% E-选择性，产率为 83-97%。1a与脂肪醛的反应产生92-94% E-选择性，除了 α-支链醛，使用 2-(二异丙基膦酰基)丙酸乙酯1b将选择性提高到 97-98% 。使用 2-膦酰基丙酸三异丙酯1c改善了与 α-支链脂肪醛的反应和Ba(OH) 2 ·8H 2 O，得到98->99%的E-选择性和高产率。在THF中使用Ba(OH) 2 ·8H 2 O的HWE反应也以高产率高度选择性地得到( E )-α-甲基-α,β-不饱和酯。