methyl 3-(3,4-dimethoxyphenyl)-2-hydroxypropanoate

• 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 3-(3,4-dimethoxyphenyl)-2-hydroxypropanoate
• 英文别名: methyl (2-rac)-3-(3,4-dimethoxyphenyl)-2-hydroxypropanoate；(±)-trimethyltanshinol；(+/-)-(R)-methyl 3-(3,4-dimethoxyphenyl)-2-hydroxypropanoate
• 化学式: C₁₂H₁₆O₅
• 分子量: 240.256
• InChiKey: UNANLNXLVVFIDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-(3,4-dimethoxyphenyl)-2-hydroxypropanoate 在 sodium hydroxide 作用下， 生成 2-hydroxy-3-(3,4-dimethoxyphenyl)propanoic acid
  参考文献：
  名称：

  Polyphenolic acids of Lithospermum ruderale (Boraginaceae). I. Isolation and structure determination of lithospermic acid

  摘要：

  DOI：

  10.1021/jo00900a028
• 作为产物：
  描述：

  Methyl 3-(3,4-dimethoxyphenyl)-2-hydroxyprop-2-enoate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以91%的产率得到methyl 3-(3,4-dimethoxyphenyl)-2-hydroxypropanoate
  参考文献：
  名称：

  Chemocontrolled reduction of aromatic α-ketoesters by NaBH4: Selective synthesis of α-hydroxy esters or 1,2-diols

  摘要：

  alpha-hydroxyesters 5a-g or diols 6a-g have been obtained in high yields by reduction of aromatic alpha-ketoesters 4 once or twice respectively by using NaBH4 as the reducer under suitable conditions. The use of a solvent that does not interact with the reagent allowed the double reduction to occur with only a slight excess of borohydride in very mild conditions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00154-8

文献信息

• Aryl Radical Activation of C–O Bonds: Copper-Catalyzed Deoxygenative Difluoromethylation of Alcohols
  作者：Aijie Cai、Wenhao Yan、Wei Liu

  DOI：10.1021/jacs.1c04254

  日期：2021.7.7

  direct use of free alcohols without purification of the xanthate esters. Mechanistic studies are consistent with the hypothesis of aryl radicals being formed and initiating the cleavage of the C–O bonds of xanthate esters, to generate alkyl radicals as the key intermediates. This aryl radical activation approach represents a new strategy for the activation of alcohols as cross-coupling partners.

  鉴于其在天然产物和药物中的普遍存在，醇是构建 C-C 键最有吸引力的起始材料之一。我们在此报告了第一个利用芳基的反应性来激活醇衍生的黄原酸酯中的 C-O 键的催化策略，从而发现了第一个催化脱氧二氟甲基化反应。在铜催化条件下，很容易从醇原料合成的各种烷基黄原酸酯被催化生成的芳基活化，并通过烷基中间体转化为烷基二氟甲烷产物。这种可扩展的协议具有广泛的底物范围和官能团耐受性，能够对复杂的药剂进行后期修饰。已开发出一种一锅法，允许直接使用游离醇而无需纯化黄原酸酯。机理研究与芳基自由基形成并引发黄原酸酯的 C-O 键断裂以产生作为关键中间体的烷基自由基的假设一致。这种芳基自由基活化方法代表了一种将醇作为交叉偶联物活化的新策略。
• Stereoselective α-Hydroxylation of Amides Using Oppolzer’s Sultam as Chiral Auxiliary
  作者：Lumin Zhang、Lili Zhu、Jun Yang、Jisheng Luo、Ran Hong

  DOI：10.1021/acs.joc.6b00068

  日期：2016.5.6

  An Oppolzer’s sultam-based highly stereoselective α-hydroxylation of amides was developed to deliver the desired products in good yield and excellent diastereoselectivity (>20/1). The generally crystalline products and the recyclability of the chiral auxiliary illustrate the practicability and scalability of the current approach.

  开发了基于Oppolzer's sultam的酰胺的高度立体选择性α-羟基化剂，以高收率和出色的非对映选择性（> 20/1）提供所需的产物。通常为晶体的产品和手性助剂的可回收性说明了当前方法的实用性和可扩展性。
• Total synthesis of (+)-pentamethylsalvianolic acid C
  作者：Benjamin L. Alford、Helmut M. Hügel

  DOI：10.1039/c3ob27478k

  日期：——

  The total synthesis of a methylated analogue of (+)-Salvianolic acid C has been achieved. Key aspects of the synthetic route include an economical Cu(I) acetylide coupling, unique carboxyl activation conditions via microwave irradiation and a novel lipase catalysed kinetic resolution of a racemic mixture of secondary alcohol Danshensu. The preparation of this methylated analogue will not only improve

  已经实现了（+）-丹酚酸C的甲基化类似物的全合成。合成路线的关键方面包括经济的乙炔铜（I）偶联，通过微波辐照的独特羧基活化条件以及新型脂肪酶催化的仲醇丹参素外消旋混合物的动力学拆分。这种甲基化类似物的制备不仅会提高生物利用度，而且还能够获得（+）-Salvianolic acid C的新的更广泛的生物活性应用。
• Synthesis of anti-HIV lithospermic acid by two diverse strategies
  作者：Tirumala G. Varadaraju、Jih Ru Hwu

  DOI：10.1039/c2ob25575h

  日期：——

  convergent route for the synthesis of the natural product (+)-lithospermic acid, which possesses anti-HIV activity, was accomplished. The (±)-trans-dihydrobenzo[b]furan core therein was prepared by two different strategies. The first strategy involved the use of a palladium-catalyzed annulation to generate an appropriately substituted benzo[b]furan ester followed by a stereoselective reduction of a carbon–carbon

  合成天然产物的有效途径 （+）-紫精酸完成了具有抗HIV活性的药物。其中的（±）-反式-二氢苯并[ b ]呋喃核是通过两种不同的策略制备的。第一个策略涉及使用钯催化的环化反应生成适当取代的苯并[ b ]呋喃酯，然后用Mg-HgCl 2-立体选择性还原碳-碳双键。甲醇。第二种策略依赖于适当取代的芳基乙酸甲酯和丁二醛之间的醛醇缩合3,4-二甲氧基苯甲醛，然后进行环化。最后，总合成（+）-紫精酸完成经由一个耦合的反式-二氢苯并[ b与对映体纯]呋喃肉桂酸乳酸甲酯。
• C₂₈ Terpenoids from Lamiaceous Plant <i>Perovskia scrophulariifolia</i>: Their Structures and Anti-neuroinflammatory Activity
  作者：Naonobu Tanaka、Kanji Niwa、Seita Kajihara、Daisuke Tsuji、Kohji Itoh、Nilufar Z. Mamadalieva、Yoshiki Kashiwada

  DOI：10.1021/acs.orglett.0c02855

  日期：2020.10.2

  Structurally unique C28 terpenoids, perovsfolins A (1) and B (2), were isolated from the aerial parts of an Uzbek medicinal plant, Perovskia scrophulariifolia (Lamiaceae). Their chemical structures including an unprecedented 6/8/6/6/6 pentacyclic carbon skeleton with a C6–C3 ester moiety were elucidated on the basis of spectroscopic analyses aided by density functional theory calculations as well as

  从乌兹别克药用植物Perovskia scrophulariifolia（唇形科）的地上部分分离出结构独特的 C 28萜类化合物，即 perovsfolins A ( 1 ) 和 B ( 2 )。基于密度泛函理论计算和化学证据辅助的光谱分析，阐明了它们的化学结构，包括前所未有的具有 C 6 -C 3酯部分的6/8/6/6/6 五环碳骨架。Perovsfolin B ( 2 ) 表现出抗神经炎症活性。