dimethyl 2-(3-oxo-1-phenylpropyl)malonate | 136917-91-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: dimethyl 2-(3-oxo-1-phenylpropyl)malonate
• 英文别名: methyl 2-methoxycarbonyl-3-phenyl-5-oxopentanoate；Dimethyl 2-(3-oxo-1-phenylpropyl)propanedioate；dimethyl 2-(3-oxo-1-phenylpropyl)propanedioate
• CAS: 136917-91-4
• 化学式: C₁₄H₁₆O₅
• 分子量: 264.278
• InChiKey: WNDVIPBSSNSAQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl 2-(3-oxo-1-phenylpropyl)malonate 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 31.5h， 生成 (E)-methyl 2-methoxycarbonyl-3-phenyl-7-O-(phenoxycarbonyloxy)-5-octenoate
  参考文献：
  名称：

  A comparison of the benzylic and the allylic group as a donor in the formal [4+2] cycloaddition to tetrahydropyrans using donor-acceptor cyclobutanes

  摘要：

  The allyl group was shown to be preferred over the benzyl group as a donor in the formal [4+2]-cyclo-addition reaction between a donor-acceptor cyclobutane and various aldehydes to give tetrahydropyrans. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2017.06.046
• 作为产物：
  描述：

  肉桂醛 、 丙二酸二甲酯 在 lithium salt of proline 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以77%的产率得到dimethyl 2-(3-oxo-1-phenylpropyl)malonate
  参考文献：
  名称：

  The Michael addition of dimethyl malonate to α,β-unsaturated aldehydes catalysed by proline lithium salt

  摘要：

  在存在10 mol%的脯氨酸锂盐的条件下，二甲基丙二酸酯与α,β-不饱和醛反应生成了高收率的迈克尔加成产物。

  DOI：

  10.1039/c39910001088

文献信息

• Polystyrene-Supported Diarylprolinol Ethers as Highly Efficient Organocatalysts for Michael-Type Reactions
  作者：Esther Alza、Sonia Sayalero、Pinar Kasaplar、Diana Almaşi、Miquel A. Pericàs

  DOI：10.1002/chem.201101730

  日期：2011.10.4

  addition of aldehydes to nitroolefins and of malonates or nitromethane to α,β‐unsaturated aldehydes. The combination of the catalytic unit, the triazole linker, and the polymeric matrix provides unprecedented substrate selectivity, in favor of linear, short‐chain aldehydes, when the organocatalyzed reaction proceeds by an enamine mechanism. High versatility is noted in reactions that proceed via an iminium

  锚固在聚苯乙烯树脂上的α，α-二苯基脯氨醇甲基和三甲基甲硅烷基醚是通过铜催化的叠氮化物-炔烃环加成反应（CuAAC）制备的。O显示的催化活性和对映选择性三甲基甲硅烷基衍生物与最著名的均相催化剂表现出的可比性相当，后者可将醛加成到硝基烯烃中，将丙二酸酯或硝基甲烷加成到α，β-不饱和醛上。当有机催化的反应通过烯胺机制进行时，催化单元，三唑连接基和聚合物基体的组合可提供前所未有的底物选择性，有利于线性短链醛。通过亚胺离子中间体进行的反应具有很高的通用性。还通过不对称迈克尔加成反应评估了聚苯乙烯负载的α，α-二苯基脯氨醇甲醚的催化行为。通常，将二芳基脯氨醇醚固定在不溶性聚苯乙烯树脂上的CuAAC具有重要的操作优势，例如高催化活性，
• Highly Diastereo- and Enantioselective Cascade Synthesis of Bicyclic Lactams in One-Pot
  作者：Yan Jiang、Luca Deiana、Rana Alimohammadzadeh、Leifeng Liu、Junliang Sun、Armando Córdova

  DOI：10.1002/ejoc.201701789

  日期：2018.3.7

  A versatile and highly stereoselective synthetic route to functionalized bi- and tricyclic lactams (up to > 20:1 dr and 99 % ee) in one pot from simple starting materials (allylic alcohols, enal ...

  一种多功能且高度立体选择性的合成路线，可在一个锅中从简单的起始材料（烯丙醇、烯醛）制备功能化的双环和三环内酰胺（高达 > 20:1 dr 和 99 % ee）。
• A Recyclable Chiral 2‐(Triphenylmethyl)pyrrolidine Organocatalyst Anchored to [60]Fullerene
  作者：Cristian Rosso、Marco G. Emma、Ada Martinelli、Marco Lombardo、Arianna Quintavalla、Claudio Trombini、Zois Syrgiannis、Maurizio Prato

  DOI：10.1002/adsc.201900009

  日期：2019.6.18

  [60]fullerene via click chemistry provides a highly efficient supported enantioselective organocatalyst, which was successfully exploited in a Michael addition of malonates to cinnamaldehydes, via iminium ion activation. The supported organocatalyst was recycled up to six times, with only a moderate decrease in terms of activity and with no loss in enantioselectivity.

  通过点击化学将衍生自（R）-吡咯烷醇的手性3-羟基-2-三苯甲基-吡咯烷与[60]富勒烯杂交，提供了一种高效的负载型对映选择性有机催化剂，该方法已成功地用于迈克尔·马来酸向肉桂醛中的丙二酸酯加成反应中。亚胺离子活化。负载的有机催化剂被循环利用多达六次，活性仅适度下降，对映选择性没有损失。
• An enantio- and diastereoselective approach to indoloquinolizidines in continuous flow
  作者：Moreshwar B. Chaudhari、Prachi Gupta、Patricia Llanes、Leijie Zhou、Nicola Zanda、Miquel A. Pericàs

  DOI：10.1039/d2ob01462a

  日期：——

  short synthesis of indoloquinolizidines. Using this approach, a highly enantioselective, solvent-free and rapid conjugate addition of dimethyl malonate to a diverse family of cinnamaldehydes in continuous flow, allowing the preparation of relevant oxodiesters in multigram amounts has been developed. The obtained Michael adducts have been used to complete an expedient diastereoselective synthesis of indoloquinolizidine

  将聚合物支持的不对称有机催化与填充床反应器中的连续流动相结合，已被用作吲哚喹啉短合成中的关键对映体测定步骤。使用这种方法，开发了一种高度对映选择性、无溶剂且快速的丙二酸二甲酯在连续流动中添加到多种肉桂醛中的方法，从而可以制备多克量的相关氧代二酯。获得的迈克尔加合物已用于通过级联 Pictet-Splengler 环化-内酰胺化在连续流中完成吲哚并喹啉西啶的便捷非对映选择性合成。还探索了在连续流中通过伸缩还原/环化将对映体纯迈克尔加合物转化为 δ-内酯。
• Distribution of Catalytic Species as an Indicator To Overcome Reproducibility Problems
  作者：Xavier Companyó、Jordi Burés

  DOI：10.1021/jacs.7b05045

  日期：2017.6.28

  Irreproducibility is a common issue in catalysis. The ordinary way to minimize it is by ensuring enhanced control over the factors that affect the reaction. When control is insufficient, some parameters can be used as indicators of the reaction performance. Herein we describe the use of the distribution of catalytic species as an indicator to map, track, and fine-tune the performance of catalytic reactions. This indicator is very sensitive and presents a quick response to variations in the reaction conditions. We have applied this new strategy to the conjugate addition of C-nucleophiles to enals via iminium intermediates, consistently achieving maximum turnover frequencies (TOF) regardless of the quality of the starting materials used. In addition, the present method has allowed us to efficiently reduce the catalyst loading to as little as 0.1 mol %, the lowest one described for this kind of reaction.

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