5-(trifluoromethyl)-4-(furan-2-yl)-dihydro-5-phenylfuran-2(3H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 5-(trifluoromethyl)-4-(furan-2-yl)-dihydro-5-phenylfuran-2(3H)-one
• 英文别名: (4S,5S)-4-(Furan-2-yl)-5-phenyl-5-(trifluoromethyl)dihydrofuran-2(3H)-one；(4S,5S)-4-(furan-2-yl)-5-phenyl-5-(trifluoromethyl)oxolan-2-one
• 化学式: C₁₅H₁₁F₃O₃
• 分子量: 296.246
• InChiKey: WEUSSVXSBSFYAI-SMDDNHRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  反-3-(2-呋喃基)丙烯醛 、 2,2,2-三氟苯乙酮 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 1,3-双(2,4,6-三甲基苯基)氯化咪唑 作用下， 以 甲苯 为溶剂， 反应 18.0h， 生成 5-(trifluoromethyl)-4-(furan-2-yl)-dihydro-5-phenylfuran-2(3H)-one 、 5-(trifluoromethyl)-4-(furan-2-yl)-dihydro-5-phenylfuran-2(3H)-one
  参考文献：
  名称：

  三氟甲基化γ丁内酯的非对映选择性合成通过N-杂环卡宾催化共轭α的极性转换，β不饱和醛

  摘要：

  描述了不同取代的α，β-不饱和醛的N-杂环卡宾催化的共轭物质。这些化合物与各种三氟甲基化的酮的偶联导致氟化γ-丁内酯的选择性形成。使用源自噻唑鎓的N-杂环卡宾，主要形成不同的立体异构体，而咪唑-2-亚基IMes导致较低的选择性和类似异构体的优选形成。

  DOI：

  10.1002/adsc.200800051

文献信息

• β-Carbon activation of saturated carboxylic esters through N-heterocyclic carbene organocatalysis
  作者：Zhenqian Fu、Jianfeng Xu、Tingshun Zhu、Wendy Wen Yi Leong、Yonggui Robin Chi

  DOI：10.1038/nchem.1710

  日期：2013.10

  The activation of the α-carbons of carboxylic esters and related carbonyl compounds to generate enolate equivalents as nucleophiles is one of the most powerful strategies in organic synthesis. We reasoned that the horizons of chemical synthesis could be greatly expanded if the typically inert β-carbons of saturated esters could be used as nucleophiles. However, despite the rather significant fundamental

  活化羧酸酯和相关羰基化合物的 α-碳以生成烯醇等价物作为亲核试剂是有机合成中最有效的策略之一。我们推断，如果饱和酯的典型惰性 β-碳可以用作亲核试剂，则化学合成的范围可以大大扩展。然而，尽管具有相当重要的基本和实用价值，但直接使用饱和羰基化合物的 β-碳作为亲核试剂仍然难以捉摸。在这里，我们报告了使用N催化活化作为亲核试剂的简单饱和酯 β-碳（β-碳活化）-杂环卡宾有机催化剂。催化产生的亲核β-碳与亲电子试剂如烯酮和亚胺发生对映选择性反应。鉴于已证明酯 α-碳具有丰富的化学性质，我们预计这种饱和酯 β-碳的催化活化模式将为新的有用反应和合成策略开辟一个有价值的新领域。
• Diastereoselective Synthesis of Trifluoromethylated γ-Butyrolactonesvia N-Heterocyclic Carbene-Catalyzed Conjugated Umpolung of α,β-Unsaturated Aldehydes
  作者：Keiichi Hirano、Isabel Piel、Frank Glorius

  DOI：10.1002/adsc.200800051

  日期：2008.5.5

  The N-heterocyclic carbene-catalyzed conjugate umpolung of differently substituted α,β-unsaturated aldehydes is described. Coupling of these compounds with a variety of trifluoromethylated ketones results in the selective formation of fluorinated γ-butyrolactones. Using thiazolium-derived N-heterocyclic carbenes, the unlike stereoisomers are formed predominantly, whereas the imidazol-2-ylidene IMes

  描述了不同取代的α，β-不饱和醛的N-杂环卡宾催化的共轭物质。这些化合物与各种三氟甲基化的酮的偶联导致氟化γ-丁内酯的选择性形成。使用源自噻唑鎓的N-杂环卡宾，主要形成不同的立体异构体，而咪唑-2-亚基IMes导致较低的选择性和类似异构体的优选形成。
• [EN] ACTIVATION OF CARBONYL &bgr;-CARBONS FOR CHEMICAL TRANSFORMATIONS<br/>[FR] ACTIVATION DE &Bgr;-CARBONES DE CARBONYLE POUR DES TRANSFORMATIONS CHIMIQUES
  申请人：UNIV NANYANG TECH

  公开号：WO2014142755A1

  公开（公告）日：2014-09-18

  The present invention relates to a method for synthesizing a compound of Formula (I) as defined herein, comprising: (i) activating a compound of Formula (II) as defined herein, by reacting said compound of Formula (II) with a compound of Formula (III) as defined herein, in the presence of a base, to obtain a compound of Formula (IV) as defined herein; and (ii) reacting the compound of Formula (IV) with an electrophile to obtain the compound of Formula (I). The present invention further relates to the organocatalysts used in the described methods and their respective uses.

  本发明涉及一种合成式(I)化合物的方法，包括：(i) 通过在碱的存在下，将式(II)化合物与式(III)化合物反应，激活式(II)化合物，以得到式(IV)化合物；以及(ii) 通过将式(IV)化合物与亲电试剂反应，得到式(I)化合物。本发明还涉及所述方法中使用的有机催化剂及其相应的用途。
• Activation of carbonyl beta-carbons for chemical transformations
  申请人：Nanyang Technological University

  公开号：US11306097B2

  公开（公告）日：2022-04-19

  The present invention relates to a method for synthesizing a compound of Formula (I) as defined herein, comprising: (i) activating a compound of Formula (II) as defined herein, by reacting said compound of Formula (II) with a compound of Formula (III) as defined herein, in the presence of a base, to obtain a compound of Formula (IV) as defined herein; and (ii) reacting the compound of Formula (IV) with an electrophile to obtain the compound of Formula (I). The present invention further relates to the organocatalysts used in the described methods and their respective uses.

  本发明涉及一种合成式（I）化合物的方法 的方法，包括： (i) 活化式（II）化合物 将所述式 (II) 化合物与式 (III) 化合物反应，得到如本文所定义的化合物 如本文所定义，在碱存在下，得到式（IV）化合物 如本文所定义；以及(ii)使式(IV)化合物与亲电子体反应，得到式(I)化合物。本发明进一步涉及所述方法中使用的有机催化剂及其各自的用途。
• ACTIVATION OF CARBONYL BETA-CARBONS FOR CHEMICAL TRANSFORMATIONS
  申请人：Nanyang Technological University

  公开号：US20160039827A1

  公开（公告）日：2016-02-11

  The present invention relates to a method for synthesizing a compound of Formula (I) as defined herein, comprising: (i) activating a compound of Formula (II) as defined herein, by reacting said compound of Formula (II) with a compound of Formula (III) as defined herein, in the presence of a base, to obtain a compound of Formula (IV) as defined herein; and (ii) reacting the compound of Formula (IV) with an electrophile to obtain the compound of Formula (I). The present invention further relates to the organocatalysts used in the described methods and their respective uses.