methyl 2-[(3,5-dimethoxyphenyl)hydroxymethyl]propenoate | 496024-82-9

• 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-[(3,5-dimethoxyphenyl)hydroxymethyl]propenoate
• 英文别名: Zhqqmyvloiiffu-uhfffaoysa-；methyl 2-[(3,5-dimethoxyphenyl)-hydroxymethyl]prop-2-enoate
• CAS: 496024-82-9
• 化学式: C₁₃H₁₆O₅
• 分子量: 252.267
• InChiKey: ZHQQMYVLOIIFFU-UHFFFAOYSA-N

物化性质

• 沸点：
  397.9±42.0 °C(predicted)
• 密度：
  1.165±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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 2-[(3,5-dimethoxyphenyl)hydroxymethyl]propenoate 在 氢溴酸 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 1-[2-carbomethoxy-3-(3,5-dimethoxyphenyl)-2-propenyl]-(3S)-acetoxypyrrolidine-2,5-dione
  参考文献：
  名称：

  An Asymmetric Synthesis of Aza Analogues of the Tricyclic Skeleton of Daphnane and the ABC Ring System of Phorbol

  摘要：

  An asymmetric synthesis of aza analogues of the ABC ring system of phorbol and related compounds containing the 5-7-6-fused framework of daphnane involved construction of the central seven-membered ring by a regioselective reduction of a chiral imide and cyclization with trifluoromethanesulfonic acid. Subsequent demethylation and oxidative dearomatization of ring C afforded an enantiopure dienone 20 with the same relative and absolute configuration at the 9- and 10-positions of the phorbol skeleton.

  DOI：

  10.1021/jo0205816
• 作为产物：
  描述：

  3,5-二甲氧基苯甲醛 、 丙烯酸甲酯（MA） 在 三乙烯二胺 作用下， 生成 methyl 2-[(3,5-dimethoxyphenyl)hydroxymethyl]propenoate
  参考文献：
  名称：

  二氢吡咯的直接合成[2,1-一个]异喹啉通过的FeCl 3推荐无氧芳构

  摘要：

  我们已经开发出一种简单的FeCl 3促进的二氢吡咯并[2,1- a ]异喹啉的合成，方法是通过二氢异喹啉与Morita-Baylis-Hillman碳酸盐的正式（3 + 2）环加成/氧化芳构化级联（产率高达96％）。通过简单的化学转化成功获得了进一步的修饰产物，提供了多种天然产物样分子（12个例子）。

  DOI：

  10.1002/adsc.201900756

文献信息

• A novel tandem Pd-catalyzed intramolecular allylic decarboxylative coupling and “diradical conjugated 1,3-dien-5-yne cycloaromatization”: An unusual ortho -selectivity in the cycloaromatization and the mechanistic implications
  作者：Satyanarayana Tummanapalli、Dhanunjaya Naidu Vangapandu、Parthasarathy Muthuraman、Sanjeeva Kambampati、Gnanakalai Shanmugavel

  DOI：10.1016/j.tetlet.2017.06.079

  日期：2017.8

  hindered cyclization products (12–23) via the unusual ortho-selective cycloaromatization; while the meta-alkoxy (1i–m, 1r–t) group provided predominantly the ortho-selective 1,3-dien-5-yne cycloaromatization products, meta-Me group (1 n–q), products formed both via ortho-selective cyclization and para-selective cyclization products in comparable ratio. A novel mechanism involving diradical species

  在催化Pd（PPh 3）4和DBU的存在下，Baylis-Hillman醇的丙酸芳基酯的多米诺骨化烯丙基重排，分子内脱羧偶联，炔丙基-丙二烯重排和双自由基1,3-二烯-5-炔环芳构化已经描述了4-苄基萘甲酸的形成。有趣的是，间位取代的丙酸酯（1i – t）通过不寻常的邻位选择性环芳烃化作用提供了空间位阻的环化产物（12 – 23）。而间烷氧基（1i – m，1r –t）组主要提供邻位选择性1,3-二烯基-5yne环芳烃化产品，meta -Me组（1  n – q），是通过邻位选择性环化和对位选择性环化产物以可比的比例形成的产物。已经提出了一种涉及双自由基物种的新机制来解释1，3-二烯-5-炔环芳构化中不寻常的邻位选择性。空间上受阻的邻位选择性环化的优先选择可能归因于具有更稳定的邻位甲氧基环己二烯基团部分（驱动力）的过渡态自由基的形成。
• A novel, tandem construction of C–N and C–C bonds: facile and one-pot transformation of the Baylis–Hillman adducts into 2-benzazepines
  作者：Deevi Basavaiah、Tummanapalli Satyanarayana

  DOI：10.1039/b310550d

  日期：——

  involving tandem construction of C-N and C-C bonds via the simultaneous Ritter and Houben-Hoesch reactions on Baylis-Hillman adducts leading to a convenient, one-pot synthesis of 2-benzazepine derivatives is described. A facile stereoselective transformation of the Baylis-Hillman adducts into (E)- and (Z)-allyl amides is also presented.

  描述了一种新颖的反应，涉及通过在Baylis-Hillman加合物上同时进行的Ritter和Houben-Hoesch反应，串联和串联构建CN和CC键，可方便地一锅合成2-苯并ze庚因衍生物。还提出了Baylis-Hillman加合物向（E）-和（Z）-烯丙基酰胺的容易的立体选择性转化。
• An Improved Protocol for the Morita‐Baylis‐Hillman Reaction Allows Unprecedented Broad Synthetic Scope
  作者：Nilton S. Camilo、Hugo Santos、Lucas A. Zeoly、Fábio S. Fernandes、Manoel T. Rodrigues、Thiago S. Silva、Samia R. Lima、José Cláudio Serafim、Aline S. B. de Oliveira、Arthur G. Carpanez、Giovanni W. Amarante、Fernando Coelho

  DOI：10.1002/ejoc.202101448

  日期：2022.3.7

  By the combination of DABCO and acetic acid under solvent-free conditions, the Morita-Baylis-Hillman reaction rate of both activated and non-activated aldehydes increased significantly. The disclosed procedure is operationally simple and is compatible with a wide array of both nucleophilic and electrophilic reaction partners.

  通过在无溶剂条件下将 DABCO 和乙酸结合，活化和未活化醛的 Morita-Baylis-Hillman 反应速率均显着提高。所公开的程序操作简单并且与多种亲核和亲电反应伙伴相容。
• Ionic liquid Supported Quinuclidine Catalyzed Morita-Baylis-Hillman Reaction
  作者：Vivek Srivastava

  DOI：10.2174/1570178620666230608122516

  日期：2023.12

  overcome this drawback, the effects of pyridinium-based ionic liquids mediated quinuclidine catalytic system for MBH reactions were studied. The method is simple, involving neat and open-flask conditions, and is compatible with a wide range of reagents. We offered general pyridinium-based ionic liquids-mediated quinuclidine catalysis mechanism that is responsible for the observed rate increase. The synthetic

  Morita-Baylis-Hillman (MBH) 反应是含羰基化合物与活性烯烃之间形成碳碳键的重要方法。然而，与富电子亲电伙伴的反应速率缓慢限制了其更广泛的应用。为了克服这一缺点，研究了吡啶鎓离子液体介导的奎宁环催化体系对MBH反应的影响。该方法简单，涉及纯净和开放烧瓶条件，并且与多种试剂兼容。我们提供了通用的基于吡啶鎓离子液体介导的奎宁环催化机制，该机制导致观察到的速率增加。MBH 加合物的合成多功能性通过天然产物 (-)-sitophilure 的重要结构单元的合成得到证明。作者预计这种基于吡啶鎓的离子液体介导的奎宁环方案可以作为 MBH 反应的通用方法。综上所述，该研究提出了一种简单有效的方法来提高MBH反应的反应速率。作者相信这种方法具有更广泛的应用潜力，并可能有助于开发新的有机合成合成策略。我们成功地将催化系统回收了 7 次，没有损失任何催化活性。作者相信这种方法具有更广泛
• Catalyst-Free Conjugate Addition of Indolizines to <i>In Situ</i>-Generated Oxidized Morita–Baylis–Hillman Adducts
  作者：Thiago S. Silva、Lucas A. Zeoly、Fernando Coelho

  DOI：10.1021/acs.joc.0c00189

  日期：2020.4.17

  Sequential one-pot 2-iodoxybenzoic acid (IBX) oxidation of Morita-Baylis-Hillman (MBH) adducts followed by catalyst-free indolizine conjugate addition was developed. The wide scopes of MBH adducts and indolizines were investigated, and densely functionalized adducts were obtained in yields of up to 94%. The conjugate addition step occurred in less than a minute at room temperature with total regioselectivity toward indolizine C3 carbon. Less nucleophilic C1 carbon was also alkylated when C3-substituted indolizines were employed as the substrate.

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