4-(4-hydroxyphenyl)-2-methylenebutyrolactone | 1447662-17-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(4-hydroxyphenyl)-2-methylenebutyrolactone
• 英文别名: 5-(4-Hydroxyphenyl)-3-methylideneoxolan-2-one；5-(4-hydroxyphenyl)-3-methylideneoxolan-2-one
• CAS: 1447662-17-0
• 化学式: C₁₁H₁₀O₃
• 分子量: 190.199
• InChiKey: WDNXWPATKPEVFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6-二甲基-2,5-环己二烯-1,4-二酮 、 4-(4-hydroxyphenyl)-2-methylenebutyrolactone 在 二氢吡啶 、 hafnium tetrakis(trifluoromethanesulfonate) 作用下， 反应 2.5h， 以32%的产率得到4-(3,5-dimethyl-1,4-benzoquinon-2-yl)-4-(4-hydroxyphenyl)-2-methylenebutanoic acid
  参考文献：
  名称：

  内酯与醌的催化氧化还原链开环合成含醌的羧酸

  摘要：

  五至八元内酯与醌的催化开环是通过氧化还原链机理实现的。在简单的三氟甲磺酸金属路易斯酸催化剂和链引发剂的低负载下，许多醌的C–H键被含羧酸的侧链有效地官能化。该方法还具有100％的原子经济性和广泛的底物范围。开发了一种抗哮喘药Seratrodast的新途径。机理研究表明，氧化还原链反应可能发生碳正离子中间体。

  DOI：

  10.1021/acs.orglett.9b01672
• 作为产物：
  描述：

  在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以106.4 mg的产率得到4-(4-hydroxyphenyl)-2-methylenebutyrolactone
  参考文献：
  名称：

  内酯与醌的催化氧化还原链开环合成含醌的羧酸

  摘要：

  五至八元内酯与醌的催化开环是通过氧化还原链机理实现的。在简单的三氟甲磺酸金属路易斯酸催化剂和链引发剂的低负载下，许多醌的C–H键被含羧酸的侧链有效地官能化。该方法还具有100％的原子经济性和广泛的底物范围。开发了一种抗哮喘药Seratrodast的新途径。机理研究表明，氧化还原链反应可能发生碳正离子中间体。

  DOI：

  10.1021/acs.orglett.9b01672

文献信息

• New α-Methylene-γ-Butyrolactone Derivatives as Potential Fungicidal Agents: Design, Synthesis and Antifungal Activities
  作者：Yongling Wu、Delong Wang、Yanqing Gao、Juntao Feng、Xing Zhang

  DOI：10.3390/molecules21020130

  日期：——

  biological activity, forty-six new ester and six new ether derivatives containing α-methylene-γ-butyrolactone moieties were synthesized, and their fungicidal activities against Colletotrichum lagenarium and Botrytis cinerea were investigated. Most of the synthesized compounds showed moderate to significant fungicidal activity. Among them, halogen atom-containing derivatives showed better activity than others

  考虑到α-亚甲基-γ-丁内酯部分是卡拉布隆结构中的主要生物官能团并具有一定的农业生物活性，46种含α-亚甲基-γ的新酯和6种新醚衍生物合成了β-丁内酯部分，并研究了它们对炭疽病菌和灰葡萄孢菌的杀真菌活性。大多数合成的化合物表现出中等至显着的杀真菌活性。其中，含卤原子的衍生物比其他化合物表现出更好的活性，尤其是化合物6a、d对C.lagenarium表现出优异的杀菌活性，IC50值为7.68和8.17 μM。构效关系（SAR）分析表明，苯环上带有吸电子基团的酯类衍生物比带有给电子基团的酯类衍生物具有更好的杀菌活性。通过启发式方法获得了定量构效关系（QSAR）模型（R2 = 0.9824，F = 203.01，S2 = 0.0083）。构建的模型揭示了对 C.lagenarium 的杀真菌活性与这些化合物的分子结构之间的强相关性。这些结果有望证明有助于低毒高效的 α-亚甲基-γ-丁内酯类杀菌剂的设计和探索。构建的模型揭示了对
• Discovery of Novel α-Methylene-γ-Butyrolactone Derivatives Containing Vanillin Moieties as Antiviral and Antifungal Agents
  作者：Hong-Wei He、Fei-Yu Wang、Danyang Zhang、Cai-Yun Chen、Dan Xu、Huan Zhou、Xili Liu、Gong Xu

  DOI：10.1021/acs.jafc.2c03632

  日期：2022.8.24

  α-methylene-γ-butyrolactone derivatives B1–B43 were designed and synthesized by structure simplification and active fragment replacement strategies, and their antiviral and antifungal activities were evaluated. The bioassay studies indicated that many target compounds possessed good to excellent antiviral activity against tobacco mosaic virus (TMV) and some of these compounds exhibited specific antifungal activities

  在烟内酯A（L1）结构的基础上，通过结构简化和活性片段置换策略，设计合成了一系列新型α-亚甲基-γ-丁内酯衍生物B1-B43，并对其抗病毒和抗真菌活性进行了评价。生物测定研究表明，许多目标化合物对烟草花叶病毒 (TMV) 具有良好至优异的抗病毒活性，其中一些化合物对Valsa mali和Fusarium graminearum表现出特定的抗真菌活性。化合物B32在体内表现出最好的抗TMV活性（灭活效果，88.9%；保护效果，65.8%；疗效，52.8%）500 mg/L，明显高于市售杀病毒剂利巴韦林和宁南霉素。化合物B32的抑制作用也通过使用绿色荧光蛋白 (GFP) 标记的 TMV 的接种试验显现。研究了化合物B32的初步抗病毒机制。透射电子显微镜 (TEM) 显示化合物B32可以破坏病毒颗粒的完整性。然后，分子对接和等温滴定量热法 (ITC) 分析进一步证明，化合物B32对 TMV 外壳蛋白表现出很强的结合亲和力，其解离常数
• New antifungal scaffold derived from a natural pharmacophore: Synthesis of α-methylene-γ-butyrolactone derivatives and their antifungal activity against Colletotrichum lagenarium
  作者：Feng Jun-Tao、Wang De-Long、Wu Yong-Ling、Yan He、Zhang Xing

  DOI：10.1016/j.bmcl.2013.05.073

  日期：2013.8

  Thirty new and thirty-four known analogues were designed and synthesized to improve the potential use of the alpha-methylene-gamma-butyrolactone ring, a natural pharmacophore. All structures were confirmed by H-1 and C-13 NMR, MS, and single-crystal X-ray diffraction analyses. The results of antifungal and cytotoxic activity indicated that the synthesized analogues showed significant inhibitory activity and limited selectivity. Compound 45 exhibited the highest antifungal activity with IC50 = 22.8 mu M but moderate cytotoxic activity with IC50 = 28.5 mu M (against BGC823 cell line) and 7.7 mu M (against HeLa cell line). Analysis of structure-activity relationships revealed that the incorporation of an aromatic ring into the beta, gamma positions of the lactone ring improved antifungal activity, and that the introduction of electron-withdrawing groups into the aromatic rings increased the activity compared with electron-donating groups. The above results identified 4-phenyl-3-phenyl-2-methylenebutyrolactone (33) as a lead scaffold for discovering and developing novel and improved crop-protection agents. (C) 2013 Elsevier Ltd. All rights reserved.
• Catalytic Redox Chain Ring Opening of Lactones with Quinones To Synthesize Quinone-Containing Carboxylic Acids
  作者：Xiao-Long Xu、Zhi Li

  DOI：10.1021/acs.orglett.9b01672

  日期：2019.7.5

  Catalytic ring opening of five- to eight-membered lactones with quinones is achieved through a redox chain mechanism. With low loading of a simple metal triflate Lewis acid catalyst and a chain initiator, C–H bonds of many quinones were efficiently functionalized with carboxylic acid-containing side chains. This method also features 100% atom economy and wide substrate scope. A novel route to the anti-asthma

  五至八元内酯与醌的催化开环是通过氧化还原链机理实现的。在简单的三氟甲磺酸金属路易斯酸催化剂和链引发剂的低负载下，许多醌的C–H键被含羧酸的侧链有效地官能化。该方法还具有100％的原子经济性和广泛的底物范围。开发了一种抗哮喘药Seratrodast的新途径。机理研究表明，氧化还原链反应可能发生碳正离子中间体。