trans-3-(p-benzyl-4-phenyl-3-methoxycarbonyl)-γ-butyrolactone | 1190364-33-0

• 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: trans-3-(p-benzyl-4-phenyl-3-methoxycarbonyl)-γ-butyrolactone
• 英文别名: Methyl 3-benzyl-5-oxo-2-phenyloxolane-3-carboxylate
• CAS: 1190364-33-0
• 化学式: C₁₉H₁₈O₄
• 分子量: 310.35
• InChiKey: UPUZVXGBHBLVLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  溴苯 、 衣康酸二甲酯 、 苯甲醛 在 1,2-二溴乙烷 、 三氟乙酸 、 cobalt(II) bromide 、 锌 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以64%的产率得到trans-3-(p-benzyl-4-phenyl-3-methoxycarbonyl)-γ-butyrolactone
  参考文献：
  名称：

  钴催化多组分方法制备新型 2,3-二-和 2,2,3-三取代 3-甲氧羰基-γ-丁内酯

  摘要：

  描述了从芳基溴化物、衣康酸二甲酯和醛或酮开始的标题丁内酯的一锅三组分合成。钴催化的多米诺过程形式上包括芳族溴化物的原位金属化、衣康酸二甲酯上的共轭加成、与羰基化合物的醛醇化反应以及最终环化成五元内酯。该程序适用于一系列具有对康酸甲酯亚基的功能化 γ-丁内酯的简明合成。

  DOI：

  10.1002/ejoc.201000698

文献信息

• A Cobalt-Catalyzed Multicomponent Approach to Novel 2,3-Di- and 2,2,3-Trisubstituted 3-Methoxycarbonyl-γ-butyrolact­ones
  作者：Camille Le Floch、Erwan Le Gall、Eric Léonel、Jihen Koubaa、Thierry Martens、Pascal Retailleau

  DOI：10.1002/ejoc.201000698

  日期：2010.9

  one-pot, three-component synthesis of the title butyrolactones starting from aryl bromides, dimethyl itaconate, and either aldehydes or ketones is described. The cobalt-catalyzed domino process formally involves the in situ metalation of an aromatic bromide, conjugate addition onto dimethyl itaconate, an aldolization reaction with a carbonyl compound and a final cyclization into a five-membered lactone

  描述了从芳基溴化物、衣康酸二甲酯和醛或酮开始的标题丁内酯的一锅三组分合成。钴催化的多米诺过程形式上包括芳族溴化物的原位金属化、衣康酸二甲酯上的共轭加成、与羰基化合物的醛醇化反应以及最终环化成五元内酯。该程序适用于一系列具有对康酸甲酯亚基的功能化 γ-丁内酯的简明合成。
• Synthesis and cytotoxic evaluation of novel paraconic acid analogs
  作者：Camille Le Floch、Erwan Le Gall、Eric Léonel、Thierry Martens、Thierry Cresteil

  DOI：10.1016/j.bmcl.2011.09.092

  日期：2011.12

  A novel class of 2,3-tri- and tetrasubstituted gamma-butyrolactones analogous to paraconic acids has been synthesized in one step using a straightforward three-component reaction among aryl bromides, dimethyl itaconate and carbonyl compounds. The in vitro cytotoxic activity of representative compounds has been evaluated against a panel of human cancer cell lines (KB, HCT116, MCF7, HL60). While most molecules exhibit a low to moderate background activity on both KB and HL60 cancer cell lines, one compound shows increased antiproliferative activities against both cell lines with IC50 values in the 10(-7)-10(-6) mol/L range. An extended evaluation indicated that this compound also inhibits PC3, SK-OV3, MCF7R and HL60R cell growth in the same fashion. (C) 2011 Elsevier Ltd. All rights reserved.
• Three-component synthesis of functionalized five-membered ring lactones under Barbier-like conditions
  作者：Camille Le Floch、Carine Bughin、Erwan Le Gall、Eric Léonel、Thierry Martens

  DOI：10.1016/j.tetlet.2009.07.038

  日期：2009.9

  Five-membered ring lactones have been synthesized using a straightforward three-component reaction among in situ-generated arylzinc reagents, dimethyl itaconate and aromatic aldehydes. This Barbier-like procedure. which is characterized by its simplicity, allows the concise synthesis of a range of highly functionalized 4,5-substituted gamma-butyrolactones. (C) 2009 Elsevier Ltd. All rights reserved.
• Real-time monitoring of a cobalt-mediated one-pot transition metal-catalyzed multicomponent reaction
  作者：Antônio E.M. Crotti、Daniel Previdi、Paulo M. Donate、J. Scott McIndoe

  DOI：10.1016/j.ica.2020.119654

  日期：2020.8

  ionization mass spectrometry (PSI-ESI-MS) and FTIR spectroscopy were used to investigate the mechanism of a like-Barbier cobalt-mediated one-pot transition metal-catalyzed multicomponent reaction (MCR). The use of charge-tagged aryl halides allowed for the detection of cobalt(II)-promoted hydrodehalogenation products. Although these products were also detected in the off-line ESI-MS monitoring, the ability

  摘要本文采用加压样品注入电喷雾电离质谱（PSI-ESI-MS）和FTIR光谱研究了类似Barbier钴介导的一锅过渡金属催化的多组分反应（MCR）的机理。使用带电荷标签的芳基卤化物可以检测钴（II）促进的加氢脱卤产物。尽管在离线ESI-MS监控中也检测到了这些产物，但是PSI-ESI-MS跟踪反应混合物组成的实时变化的能力证明了钴（II​​）是造成不良转化的原因。在此MCR中，钴（II）促进的加氢脱卤反应作为副反应的发生尚未在以前的机械方案中进行考虑，并且代表了重要的机械考虑因素。