3-(2,6-dihydroxyphenyl)isobenzofuran-1(3H)-one | 731773-37-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 3-(2,6-dihydroxyphenyl)isobenzofuran-1(3H)-one
• 英文别名: 3-(2,6-Dihydroxyphenyl)phthalide；3-(2,6-dihydroxyphenyl)-3H-2-benzofuran-1-one
• CAS: 731773-37-8
• 化学式: C₁₄H₁₀O₄
• 分子量: 242.231
• InChiKey: KYQBTDRMHAHCJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 3-(2,6-dihydroxyphenyl)isobenzofuran-1(3H)-one 在 硫酸 作用下， 反应 0.5h， 以76%的产率得到2-(3-oxo-1,3-dihydroisobenzofuran-1-yl)-1,3-phenylene diacetate
  参考文献：
  名称：

  区域特异性合成3-（2,6-二羟基苯基）邻苯二甲酸酯：在异黄霉素和冷冻柠檬酸合成中的应用

  摘要：

  已经开发出DBU催化的邻苯二甲酸和1，3-二酮的缩合反应，是合成3-取代的邻苯二甲酸酯的通用方法。该方法与乙酸汞介导的氧化芳构化相结合，已被用于异雌霉素（9）和冷柠檬酸（10）的区域特异性合成。

  DOI：

  10.1016/j.tet.2007.08.048
• 作为产物：
  描述：

  3-羟基异苯并呋喃-1(3H)-酮 在 mercury(II) diacetate 、 sodium acetate 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 12.33h， 生成 3-(2,6-dihydroxyphenyl)isobenzofuran-1(3H)-one
  参考文献：
  名称：

  Synthesis and Antiproliferative Activity of C-3 Functionalized Isobenzofuran-1(3H)-ones

  摘要：

  通过缩合、芳构化和乙酰化反应合成了系列十三种C-3功能化的异苯并呋喃-1(3H)-酮（苯酞类）。核磁共振（一维和二维实验）、红外光谱和质谱分析证实了合成化合物的身份。这些物质通过MTT细胞毒性试验在体外对U937（淋巴瘤）和K562（髓性白血病）癌细胞系进行了生物活性测试。某些衍生物在100 µM浓度下抑制了90%的细胞存活率。此外，两种苯酞类化合物显示出比依托泊苷（VP16）更强的生物活性，依托泊苷是一种在试验中用作阳性对照的商用药物。计算了所评估化合物的计算机模拟药物性质，并讨论了结果。

  DOI：

  10.3390/molecules18021881

文献信息

• Regiospecific synthesis of isopestacin, a naturally occurring isobenzofuranone antioxidant
  作者：Pallab Pahari、Bidyut Senapati、Dipakranjan Mal

  DOI：10.1016/j.tetlet.2004.04.175

  日期：2004.6

  A DBU promoted aldol cyclocondensation of hydroxyisobenzofuranone 15 with cyclohexane-1,3-dione, followed by aromatization has resulted in the first short synthesis of isopestacin (1).

  DBU促进了羟基异苯并呋喃酮15与环己烷1,3-二酮的羟醛缩合反应，然后进行芳构化，首次合成了异黄霉素（1）。
• Regiospecific synthesis of 3-(2,6-dihydroxyphenyl)phthalides: application to the synthesis of isopestacin and cryphonectric acid
  作者：Dipakranjan Mal、Pallab Pahari、Saroj Ranjan De

  DOI：10.1016/j.tet.2007.08.048

  日期：2007.11

  DBU catalyzed condensation of phthalaldehydic acids and 1,3-diketones has been developed to be a general method for the synthesis of 3-substituted phthalides. This method, in combination with mercuric acetate mediated oxidative aromatization has been utilized for the regiospecific synthesis of isopestacin (9) and cryphonectric acid (10).

  已经开发出DBU催化的邻苯二甲酸和1，3-二酮的缩合反应，是合成3-取代的邻苯二甲酸酯的通用方法。该方法与乙酸汞介导的氧化芳构化相结合，已被用于异雌霉素（9）和冷柠檬酸（10）的区域特异性合成。
• Design, synthesis, and biological evaluation of catalpalactone and its analogs
  作者：Jianchun Zhao、Dan Chen、Xiaochen Niu、Hongwei Zhang、Junfei Wang、Wei Zhang

  DOI：10.1007/s00044-022-02878-y

  日期：2022.5

  Ten catalpalactone derivatives were designed, synthesized, and their structures were identified by 1H NMR, 13C NMR, and HRMS. All the analogs were evaluated for antimicrobial, cytotoxic activities and insecticidal activities. Compound g bearing α,β-unsaturated six-member lactone ring showed excellent inhibitory effect on the tested pathogens. Compounds d and g showed potential antibacterial activities

  设计、合成了十种梓醇衍生物，并通过1 H NMR、13 C NMR和HRMS对其结构进行了鉴定。评估了所有类似物的抗微生物、细胞毒活性和杀虫活性。带有α,β-不饱和六元内酯环的化合物g对受试病原体表现出优异的抑制作用。化合物d和g对大肠杆菌、金黄色葡萄球菌和黄微球菌显示出潜在的抗菌活性，而化合物g和catalpalactone显示出有效的细胞毒活性。化合物d, g , h-4和 catalpalactone 对盐水虾表现出中等致死活性。我们提出α,β-不饱和六元内酯环是抗菌、细胞毒活性和杀虫活性的基本结构。首次报道了梓醇及其类似物的抗菌活性。进行了梓醇和g在Wistar大鼠体内的药代动力学。研究结果为梓内酯的进一步研究，特别是药物开发和结构优化提供了有价值的参考。
• Synthetic Analogues of the Natural Compound Cryphonectric Acid Interfere with Photosynthetic Machinery through Two Different Mechanisms
  作者：Róbson Ricardo Teixeira、Wagner Luiz Pereira、Deborah Campos Tomaz、Fabrício Marques de Oliveira、Samuele Giberti、Giuseppe Forlani

  DOI：10.1021/jf400698j

  日期：2013.6.12

  A series of isobenzofuran-1(3H)-ones (phthalides), analogues of the naturally occurring phytotoxin cryphonectric acid, were designed, synthesized, and fully characterized by NMR, IR, and MS analyses. Their synthesis was achieved via condensation, aromatization, and acetylation reactions. The measurement of the electron transport chain in spinach chloroplasts showed that several derivatives are capable of interfering with the photosynthetic apparatus. Few of them were found to inhibit the basal rate, but a significant inhibition was brought about only at concentrations exceeding 50 mu M. Some other analogues acted as uncouplers or energy transfer inhibitors, with a remarkably higher effectiveness. Isobenzofuranone addition to the culture medium inhibited the growth of the cyanobacterium,Synechococcus elongatus, with patterns consistent with the effects measured in vitro upon isolated chloroplasts. The most active derivatives, being able to completely suppress algal growth at 20 mu M, may represent structures to be exploited for the design of new active ingredients for weed control.
• Synthesis and Antiproliferative Activity of C-3 Functionalized Isobenzofuran-1(3H)-ones
  作者：Róbson Teixeira、Gustavo Bressan、Wagner Pereira、Joana Ferreira、Fabrício de Oliveira、Deborah Thomaz

  DOI：10.3390/molecules18021881

  日期：——

  A series of thirteen C-3 functionalized isobenzofuran-1(3H)-ones (phtalides) was synthesized via condensation, aromatization, and acetylation reactions. NMR (one and two dimensional experiments), IR, and mass spectrometry analysis allowed confirmation of the identity of the synthesized compounds. The substances were submitted to in vitro bioassays against U937 (lymphoma) and K562 (myeloid leukemia) cancer cell lines using the MTT cytotoxicity assay. Some derivatives inhibited 90% of cell viability at 100 µM. Also, two phtalides presented biological activity superior than that of etoposide (VP16), a commercial drug used as a positive control in the assays. In silico drug properties of the evaluated compounds were calculated and the results are discussed.

  通过缩合、芳构化和乙酰化反应合成了系列十三种C-3功能化的异苯并呋喃-1(3H)-酮（苯酞类）。核磁共振（一维和二维实验）、红外光谱和质谱分析证实了合成化合物的身份。这些物质通过MTT细胞毒性试验在体外对U937（淋巴瘤）和K562（髓性白血病）癌细胞系进行了生物活性测试。某些衍生物在100 µM浓度下抑制了90%的细胞存活率。此外，两种苯酞类化合物显示出比依托泊苷（VP16）更强的生物活性，依托泊苷是一种在试验中用作阳性对照的商用药物。计算了所评估化合物的计算机模拟药物性质，并讨论了结果。