cis-4-methyl-2-phenyl-γ-butyrolactone

• 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: cis-4-methyl-2-phenyl-γ-butyrolactone
• 英文别名: 3-phenyl-5-methyltetrahydrofuran-2-one；5-methyl-3-phenyldihydrofuran-2(3H)-one；(3S,5S)-5-methyl-3-phenyloxolan-2-one
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: CBUFPCXFXMRPLA-WPRPVWTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-硝基-4-苯基戊-2-酮 在 sodium tetrahydroborate 、 溶剂黄146 、 sodium nitrite 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 0.25h， 生成 cis-4-methyl-2-phenyl-γ-butyrolactone 、 trans-4-methyl-2-phenyl-γ-butyrolactone
  参考文献：
  名称：

  Small Changes Result in Large Differences: Discovery of (−)-Incrustoporin Derivatives as Novel Antiviral and Antifungal Agents

  摘要：

  On the basis of the structure of natural product (-)-incrustoporin (1), a series of lactone compounds 4a-i and 5a-i were designed and synthesized from nitroolefin. The antiviral and antifungal activities of these compounds were evaluated in vitro and in vivo. The small changes between 4 and 5 at the 3,4-position result in large differences in bioactivities. Compounds 4 exhibited significantly higher antiviral activity against tobacco mosaic virus (TMV) than dehydro compounds 5. However, the antifungal activity of 4 is relatively lower than that of 5. Compounds 4a, 4c, and 4i with excellent in vivo anti-TMV activity emerged as new antiviral lead compounds. Compounds 5d-g showed superiority over the commercial fungicides chlorothalonil and carbendazim against Cercospora arachidicola Hor at 50 mg kg(-1). The present study provides fundamental support for the development and optimization of (-)-incrustoporin derivatives as potential inhibitors of plant virus and pathogenic fungi.

  DOI：

  10.1021/jf503060k

文献信息

• (HMe2SiCH2)2: A Useful Reagent for B(C6F5)3-Catalyzed Reduction–Lactonization of Keto Acids: Concise Syntheses of (–)-cis-Whisky and (–)-cis-Cognac Lactones
  作者：Zhenlei Song、Hengmu Xie、Ji Lu、Yingying Gui、Lu Gao

  DOI：10.1055/s-0036-1588488

  日期：2017.11

  (HMe2SiCH2)2 has been utilized as a useful reagent for B(C6F5)3-catalyzed reduction–lactonization of keto acids to synthesize γ- and δ-lactones. The process led concisely to (–)-cis-whisky and (–)-cis-cognac lactones in respective overall yields of 32% and 36%.

  (HMe2SiCH2)2 已被用作 B(C6F5)3 催化的酮酸还原-内酯化合成γ-和δ-内酯的有用试剂。该过程简明地导致 (-)-cis-whisky 和 ​​(-)-cis-cognac 内酯的总产率分别为 32% 和 36%。
• Calcium(II)- and Triflimide-Catalyzed Intramolecular Hydroacyloxylation of Unactivated Alkenes in Hexafluoroisopropanol
  作者：Chenxiao Qi、Shengwen Yang、Vincent Gandon、David Lebœuf

  DOI：10.1021/acs.orglett.9b02705

  日期：2019.9.20

  hydroacyloxylation of unactivated alkenes, offering a streamlined access to relevant γ-lactones, which features the utilization of either a calcium(II) salt or triflimide as a catalyst in hexafluoroisopropanol. This method could be applied to the synthesis of natural products and the late-stage functionalization of natural and bioactive molecules. Additionally, DFT computations were used to elucidate the twist

  我们报告了未活化烯烃的有效分子内氢酰氧基化作用，提供了对相关γ-内酯的流线型通道，其特征在于利用了钙盐（II）或三氟甲酰亚胺作为六氟异丙醇中的催化剂。该方法可用于天然产物的合成以及天然和生物活性分子的后期功能化。此外，DFT计算用于阐明在未活化烯烃的加氢酰胺化和加氢酰氧基化之间有关5和6元环形成的反应性扭曲。
• An access to highly enantioenriched <i>cis</i>-3,5-disubstituted γ-lactones from α-bromoacetate and silyl enol ether
  作者：Ha Rim Lee、Seo Yun Kim、Min Ji Park、Yong Sun Park

  DOI：10.1039/d1ob01403j

  日期：——

  highly enantioenriched cis-3,5-disubstituted γ-lactones has been developed by the AgOTf-promoted nucleophilic substitution of α-bromoacetates with silyl enol ethers and subsequent reductive lactonization. The utility of this synthetic method was further demonstrated through the concise stereodivergent synthesis of cis- and trans-2,4-disubstituted tetrahydrofurans.

  通过 AgOTf 促进 α-溴乙酸酯与甲硅烷基烯醇醚的亲核取代和随后的还原内酯化，开发了一种高度对映体富集的顺式-3,5-二取代 γ-内酯的新合成策略。通过顺式和反式-2,4-二取代四氢呋喃的简洁立体发散合成进一步证明了这种合成方法的实用性。
• Phase-transfer-catalyzed conversion of alkynes to lactones induced by manganese carbonyl complexes
  作者：Chin Hsien Wang、Howard Alper

  DOI：10.1021/jo00352a037

  日期：1986.1
• Small Changes Result in Large Differences: Discovery of (−)-Incrustoporin Derivatives as Novel Antiviral and Antifungal Agents
  作者：Aidang Lu、Jinjin Wang、Tengjiao Liu、Jian Han、Yinhui Li、Min Su、Jianxin Chen、Hui Zhang、Lizhong Wang、Qingmin Wang

  DOI：10.1021/jf503060k

  日期：2014.9.3

  On the basis of the structure of natural product (-)-incrustoporin (1), a series of lactone compounds 4a-i and 5a-i were designed and synthesized from nitroolefin. The antiviral and antifungal activities of these compounds were evaluated in vitro and in vivo. The small changes between 4 and 5 at the 3,4-position result in large differences in bioactivities. Compounds 4 exhibited significantly higher antiviral activity against tobacco mosaic virus (TMV) than dehydro compounds 5. However, the antifungal activity of 4 is relatively lower than that of 5. Compounds 4a, 4c, and 4i with excellent in vivo anti-TMV activity emerged as new antiviral lead compounds. Compounds 5d-g showed superiority over the commercial fungicides chlorothalonil and carbendazim against Cercospora arachidicola Hor at 50 mg kg(-1). The present study provides fundamental support for the development and optimization of (-)-incrustoporin derivatives as potential inhibitors of plant virus and pathogenic fungi.