methyl 4-(4-hydroxy-2-oxo-2H-chromen-3-yl)-2-oxo-4-phenylbutanoate | 1234199-86-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: methyl 4-(4-hydroxy-2-oxo-2H-chromen-3-yl)-2-oxo-4-phenylbutanoate
• 英文别名: methyl-4-(4-hydroxy-2-oxo-2H-chromen-3-yl)-2-oxo-4-(p-tolyl)butanoate；(S)-methyl 4-(4-hydroxy-2-oxo-2H-chromen-3-yl)-2-oxo-4-phenylbutanoate；(S)-4-(4-hydroxy-2-oxo-2H-chromen-3-yl)-4-phenyl-2-oxo-butyric acid methyl ester
• CAS: 1234199-86-0
• 化学式: C₂₀H₁₆O₆
• 分子量: 352.343
• InChiKey: OVITWDIQYOYMFY-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  93.81
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  4-羟基香豆素 、 methyl 4-phenyl-2-oxo-3-butenoate 在 C₃₇H₅₇N₃O₄ 作用下， 以 乙醚 为溶剂， 反应 12.0h， 以96%的产率得到methyl 4-(4-hydroxy-2-oxo-2H-chromen-3-yl)-2-oxo-4-phenylbutanoate
  参考文献：
  名称：

  异甜菊醇衍生的叔胺-方酸酰胺催化剂催化香豆素的对映选择性合成

  摘要：

  一种新的叔胺-方酰胺有机催化剂已成功开发并应用于4-羟基香豆素与β,γ-不饱和α-酮酯的不对称迈克尔加成反应。该催化剂体系在温和的反应条件下以 1 mol% 的低催化剂负载量表现良好。以良好至高产率（高达 97%）和高对映选择性（高达 96% ee）获得了一系列香豆素衍生物。

  DOI：

  10.1002/chir.23401

文献信息

• Organocatalytic asymmetric conjugate addition of cyclic 1,3-dicarbonyl compounds to β,γ-unsaturated α-ketoesters
  作者：Jin-jia Wang、Jin-hua Lao、Zhi-peng Hu、Rui-Jiong Lu、Shao-zhen Nie、Quan-sheng Du、Ming Yan

  DOI：10.3998/ark.5550190.0011.922

  日期：——

  The conjugate addition of cyclic 1,3-dicarbonyl compounds to β,γ-unsaturated α-keto-esters was studied using a series of chiral bifunctional organocatalysts. Takemoto’s catalyst was found to be most efficient for this transformation. Excellent yields and good enantioselectivities were achieved for a variety of β,γ-unsaturated α-keto-esters and cyclic 1,3-dicarbonyl compounds. A bifunctional catalytic

  使用一系列手性双功能有机催化剂研究了环状 1,3-二羰基化合物与 β,γ-不饱和 α-酮酯的共轭加成。竹本的催化剂被发现对这种转变最有效。各种 β,γ-不饱和 α-酮酯和环状 1,3-二羰基化合物均获得了优异的产率和良好的对映选择性。提出了一种双功能催化机制。该方法为手性香豆素衍生物提供了一条新的不对称合成路线。
• Conjugate Addition of Carbon Acids to β,γ-Unsaturated α-Keto Esters: Product Tautomerism and Applications for Asymmetric Synthesis of Benzo[<i>a</i>]phenazin-5-ol Derivatives
  作者：Rinat S. Tukhvatshin、Alexander S. Kucherenko、Yulia V. Nelyubina、Sergei G. Zlotin

  DOI：10.1021/acs.joc.9b02021

  日期：2019.11.1

  by the asymmetric Michael reactions of cyclic carbon acids with β,γ-unsaturated α-keto esters and the chemical shift of the α-proton in starting nucleophilic substrates was revealed which makes equilibration predictable. New tetrahydropyran-fused benzo[a]phenazins were enantioselectively (up to 99% ee) synthesized from β,γ-unsaturated α-keto esters and benzo[a]phenazin-5-ol, a powerful anti-cancer agent

  揭示了由环状碳酸与β，γ-不饱和α-酮酯的不对称迈克尔反应生成的互变异构产物的平衡比与起始亲核底物中α-质子的化学位移之间的相关性，这使得可预测平衡。由β，γ-不饱和α-酮酯和强效抗癌剂苯并[a]吩嗪-5-醇对映体选择性合成（高达99％ee）对映体，合成了新的四氢吡喃并苯并[a]吩嗪。证明了催化剂Ia在催化反应中的易回收性。
• Azetidine-Derived Dinuclear Zinc-Catalyzed Asymmetric Conjugate Addition of Bioactive Heterocycles to β,γ-Unsaturated α-Keto esters
  作者：Shanshan Liu、Zhi-Hua Xu、Xi Wang、Hao-Ran Zhu、Min-Can Wang

  DOI：10.1021/acs.joc.9b02046

  日期：2019.11.1

  A general AzePhenol dinuclear zinc catalytic system has been successfully developed and applied into the asymmetric Michael addition of 4-hydroxyl pyrones and 4-hydroxycoumarins to β,γ-unsaturated α-keto esters. Excellent yields (up to 99%) and high enantioselectivities (up to 94% ee) are obtained for a wide range of substrates under mild conditions in the absence of additives. This bimetallic catalytic

  已成功开发出通用的AzePhenol双核锌催化体系，并将其应用于将4-羟基吡喃酮和4-羟基香豆素不对称迈克尔加成到β，γ-不饱和α-酮酸酯上。在温和条件下没有添加剂的情况下，对于多种底物，均具有出色的收率（最高99％）和高对映选择性（最高94％ee）。这种双金属催化方法代表了一种新的有效的不对称合成方案，可以访问具有药理学意义的多种生物活性化合物。提出了可能的机制来解释不对称感应的起源。
• Enantioselective Synthesis of Coumarins Catalyzed by Chiral Squaramide
  作者：Zhiwei Ma、Zhijing Liu、Chuanchuan Wang、Degang Ding、Juntao Liu、Xiaopei Chen、Guangwei Geng

  DOI：10.2174/1570178619666220309155353

  日期：2022.11

  4-hydroxycoumarin to β,γ-unsaturated α-ketoesters. The catalyst system performed well with a low catalyst loading of 1 mol% under mild reaction conditions. A series of coumarin derivatives were obtained with good yields and enantioselectivities

  【摘要】：成功开发了一种新型手性叔胺-方酸酰胺,并应用于4-羟基香豆素与β,γ-不饱和α-酮酯的不对称迈克尔加成反应。该催化剂体系在温和的反应条件下以 1 mol% 的低催化剂负载量表现良好。以良好的收率和对映选择性获得了一系列香豆素衍生物