methyl p-methoxybenzyloxyacetate | 51759-07-0

• 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 p-methoxybenzyloxyacetate
• 英文别名: (4-methoxybenzyloxy)acetic acid methyl ester；methyl 2-(4-methoxybenzyloxy)acetate；2-(p-methoxybenzyloxy)-acetic acid methyl ester；methyl 2-[(4-methoxyphenyl)methoxy]acetate
• CAS: 51759-07-0
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: PFSLSOYNJRVULY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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 p-methoxybenzyloxyacetate 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 、 戴斯-马丁氧化剂 、 三苯基膦 、 methyloxirane 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 128.0h， 生成 4-(4-methoxybenzyloxy)butanoic acid methyl ester
  参考文献：
  名称：

  Synthesis of 13C-labeled γ-hydroxybutyrates for EPR studies with 4-hydroxybutyryl-CoA dehydratase

  摘要：

  4-Hydroxybutyryl-CoA dehydratase from Clostridium aminobutyricum catalyses the reversible dehydration of its substrate 4-hydroxybutyryl-CoA (4-HB-CoA) to crotonyl CoA. The enzyme contains one [4Fe-4S](2+) cluster and one flavin adenine dinucleotide (FAD) molecule per homotetramer. Incubation of the enzyme with its substrate under equilibrium conditions followed by freezing at 77 K induced the EPR-spectrum of a neutral flavin semiquinone (g = 2.005, linewidth 2.1 mT), while at 10 K additional signals were detected. In an attempt to characterize these signals, 4-HB-CoA molecules specifically labeled with C-13 have been synthesized. This was achieved via C-13-labeled gamma-butyrolactones, which were obtained from C-13-labeled bromoacetic acids by efficient synthetic routes. Incubation of the C-13-labeled 4-hydroxybutyrate-CoA molecules with 4-hydroxybutyryi-CoA dehydratase did not lead to marked broadening of the signals.(C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2004.09.001
• 作为产物：
  描述：

  甲醇 、 (4-甲氧基苄氧基)乙酸 在 对甲苯磺酸 作用下， 反应 4.0h， 生成 methyl p-methoxybenzyloxyacetate
  参考文献：
  名称：

  Enantioselective Synthesis of (+)-Isobretonin A

  摘要：

  An enantioselective synthesis of (+)-isobretonin A is described. The chiral glycerol moiety was enantioselectively prepared by reduction of an optically active beta-keto sulfoxide. The all-trans trienic part of the molecule was stereoselectively synthesized via reductive elimination of a 1,6-dibenzoate 2,4-diene with sodium amalgam.

  DOI：

  10.1021/jo960134o

文献信息

• Total Synthesis of the Boron-Containing Ion Carrier Antibiotic Macrodiolide Tartrolon B
  作者：Johann Mulzer、Markus Berger

  DOI：10.1021/jo035391p

  日期：2004.2.1

  The first total synthesis of the boron-containing macrodiolide antibiotic tartrolon B is reported in full detail. Two convergent approaches to the target compound are described, the first of which eventually failed, due to sensitive functionality. In the second, successful route the key step was a stereoselective boron-mediated aldol addition of a bicyclic acetonide protected ketone to a diene-aldehyde

  详细报道了含硼的大乙交酯抗生素tartrolon B的第一个全合成。描述了两种针对目标化合物的融合方法，由于敏感的功能，第一种方法最终失败。在第二条成功的途径中，关键步骤是将双环丙酮化物保护的酮立体选择性地由硼介导的羟醛加成到二烯醛中。在这种情况下，使用Yamaguchi二聚化大内酯化残基可以完成合成而没有重大问题。
• [EN] TRIAZOLE DERIVATIVES AS TACHYKININ RECEPTOR ANTAGONISTS<br/>[FR] DERIVES DE TRIAZOLE EN TANT QU'ANTAGONISTES DES RECEPTEURS DE LA TACHYKININE
  申请人：LILLY CO ELI

  公开号：WO2003091226A1

  公开（公告）日：2003-11-06

  This application relates to a compound of Formula (I) or a pharmaceutically acceptable salt thereof, pharmaceutical compositions thereof, and its use as an inhibitor of the NK-1 subtype of tachykinin receptors, as well as a process for its preparation and intermediates therefor. (I) wherein: D is a C1-C3 alkane-diyl; R1 is phenyl, which is optionally substituted with one to three substitutents indpendently selected from the group consisting of halo, C1-C4 alkyl, C1-C4 alkoxy, cyano, difluoromethyl, trifluoromethyl, and trifluoromethoxy; R4 is a radical selected from the group consisting of: (IA), (IB), (IC), (ID), (IE), (IF), (IG), (IH)

  这个应用涉及到Formula (I)的化合物或其药用盐，以及其药物组合物，以及其作为NK-1亚型的催吐肽受体抑制剂的用途，以及其制备方法和中间体。其中：D是C1-C3烷二基；R1是苯基，可以选择地用来自卤素、C1-C4烷基、C1-C4烷氧基、氰基、二氟甲基、三氟甲基和三氟甲氧基的一到三个取代基中的任意一个取代基取代；R4是从以下组成的基团中选择的基团：(IA)、(IB)、(IC)、(ID)、(IE)、(IF)、(IG)、(IH)
• Mechanism of the Cobalt Oxazoline Palladacycle (COP)-Catalyzed Asymmetric Synthesis of Allylic Esters
  作者：Jeffrey S. Cannon、Stefan F. Kirsch、Larry E. Overman、Helen F. Sneddon

  DOI：10.1021/ja106688j

  日期：2010.11.3

  labeling experiments establishing that the reaction proceeds in an overall antarafacial fashion; (c) secondary deuterium kinetic isotope effects that suggest substantial rehybridization at both C1 and C3 in the rate-limiting step; and (d) DFT computational studies (B3-LYP/def2-TZVP) that provide evidence for bidentate substrate-bound intermediates and an anti-oxypalladation/syn-deoxypalladation pathway

  由钯 (II) 配合物 [COP-OAc](2) 催化的 (Z)-烯丙基三氯乙酰亚胺酯的催化对映选择性 S(N)2' 置换是一种广泛用于手性支链烯丙基酯不对称合成的方法。报告了各种旨在阐明催化机制的性质及其速率和对映体决定步骤的实验。主要发现包括以下内容：(a) 证明存在多种桥接二钯配合物并构成 COP 催化剂的静止状态（但是，单体钯 (II) 配合物可能参与催化循环）；(b) 确定反应以整体反面方式进行的标记实验；(c) 二次氘动力学同位素效应，表明在限速步骤中 C1 和 C3 处发生了大量再杂交；(d) DFT 计算研究 (B3-LYP/def2-TZVP)，为双齿底物结合中间体和抗氧化钯化/syn-deoxypalladation 途径提供证据。这些结果与一种新机制一致，在该机制中，亚胺酸氮螯合形成阳离子钯 (II) 中间体，激活烯烃以在对映体决定步骤中受到外部羧酸盐的攻击。酰氧基钯
• Synthesis of Cyclopamine Using a Biomimetic and Diastereoselective Approach
  作者：Athanassios Giannis、Philipp Heretsch、Vasiliki Sarli、Anne Stößel

  DOI：10.1002/anie.200902520

  日期：2009.10.5

  From Homer to hedgehog: Cyclopamine, the first inhibitor of the hedgehog signaling pathway, causes cyclopia in embryos but in adults it is a potent anticancer drug. A concise biomimetic and diastereoselective synthesis of cyclopamine (2) starting from commercially available dehydroepiandrosterone (1) now also provides access to several analogues.

  从荷马到刺猬：刺猬蛋白信号通路的第一个抑制剂环巴胺会在胚胎中引起Cyclopia，但在成年犬中它是一种有效的抗癌药物。现在，从市售的脱氢表雄酮（1）开始的简明仿生和非对映选择性合成环巴胺（2）也提供了几种类似物的途径。
• Efficient Synthesis of Differentiated<i>syn</i>-1,2-Diol Derivatives by Asymmetric Transfer Hydrogenation-Dynamic Kinetic Resolution of α-Alkoxy-Substituted β-Ketoesters
  作者：Laure Monnereau、Damien Cartigny、Michelangelo Scalone、Tahar Ayad、Virginie Ratovelomanana-Vidal

  DOI：10.1002/chem.201501884

  日期：2015.8.10

  Asymmetric transfer hydrogenation was applied to a wide range of racemic aryl α‐alkoxy‐β‐ketoesters in the presence of well‐defined, commercially available, chiral catalyst RuII–(N‐p‐toluenesulfonyl‐1,2‐diphenylethylenediamine) and a 5:2 mixture of formic acid and triethylamine as the hydrogen source. Under these conditions, dynamic kinetic resolution was efficiently promoted to provide the corresponding

  不对称转移氢化物应用于广泛范围外消旋芳α -烷氧基- β酮酯的在定义明确的，可商购的手性催化剂的Ru的存在II - （ñ - p甲苯磺酰基-1,2-二苯基）和甲酸和三乙胺的5：2混合物作为氢源。在这些条件下，有效地促进了动态动力学拆分，从而提供了相应的衍生自取代的芳族和杂芳族醛的顺式α-烷氧基-β-羟基酯，具有非对映选择性高（非对映体比（dr）> 99：1），几乎完美对映选择性（对映体过量（ee）> 99％）。此外，在对反应条件进行了广泛筛选之后，使用Ru II和Rh III系留的预催化剂将这一过程扩展到了更具挑战性的带有烯基，炔基和烷基取代基的底物，从而提供了相应的合成α-烷氧基β-羟基酯具有出色的对映控制（高达99％  ee）和良好至完美的非对映控制（dr> 99：1）。最后，本方案的合成效用通过应用于不对称合成手性酯（2 S）-2-乙氧基-3-（4-羟基苯基）丙酸酯，在许多过氧化物酶体中是重要的药效团。增殖激活受体α/