7-羟基-5-甲氧基-3H-2-苯并呋喃-1-酮 | 24953-77-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 中文名称: 7-羟基-5-甲氧基-3H-2-苯并呋喃-1-酮
• 英文名称: 5-methoxy-7-hydroxyphthalide
• 英文别名: 7-hydroxy-5-methoxyisobenzofuran-1(3H)-one；1(3H)-Isobenzofuranone, 7-hydroxy-5-methoxy-；7-hydroxy-5-methoxy-3H-2-benzofuran-1-one
• CAS: 24953-77-3
• 化学式: C₉H₈O₄
• 分子量: 180.16
• InChiKey: DQVAVEZQPWBKEW-UHFFFAOYSA-N

物化性质

• 熔点：
  184-184.5 °C
• 沸点：
  457.0±45.0 °C(Predicted)
• 密度：
  1.402±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-羟基-5-甲氧基-3H-2-苯并呋喃-1-酮 在 2-双环己基膦-2',6'-二甲氧基联苯 、 吡啶 、 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium carbonate 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 4.0h， 生成 5-methoxy-7-methylisobenzofuran-1(3H)-one
  参考文献：
  名称：

  Total Synthesis of Tetarimycin A, (±)-Naphthacemycin A₉, and (±)-Fasamycin A: Structure–Activity Relationship Studies against Drug-Resistant Bacteria

  摘要：

  Making use of a reductive olefin coupling reaction and Michael-Dieckmann condensation as two key operations, we have completed a concise total synthesis of tetarimycin A, (+/-)-naphthacemycin A(9), and (+/-)-fasamycin A in a highly convergent and practical protocol. Synthetic procedures thus developed have also been applied to provide related analogues for structure-activity relationship studies, thereby coming to the conclusion that the free hydroxyl group at C-10 is essential for exerting inhibitory activities against a panel of Gram-positive bacteria, including drug-resistant strains VRE and MRSA.

  DOI：

  10.1021/acs.joc.8b00802
• 作为产物：
  描述：

  3,5-二甲氧基苄醇 在 三氯化硼 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 12.5h， 生成 7-羟基-5-甲氧基-3H-2-苯并呋喃-1-酮
  参考文献：
  名称：

  Total Synthesis of Tetarimycin A, (±)-Naphthacemycin A₉, and (±)-Fasamycin A: Structure–Activity Relationship Studies against Drug-Resistant Bacteria

  摘要：

  Making use of a reductive olefin coupling reaction and Michael-Dieckmann condensation as two key operations, we have completed a concise total synthesis of tetarimycin A, (+/-)-naphthacemycin A(9), and (+/-)-fasamycin A in a highly convergent and practical protocol. Synthetic procedures thus developed have also been applied to provide related analogues for structure-activity relationship studies, thereby coming to the conclusion that the free hydroxyl group at C-10 is essential for exerting inhibitory activities against a panel of Gram-positive bacteria, including drug-resistant strains VRE and MRSA.

  DOI：

  10.1021/acs.joc.8b00802

文献信息

• Concise Chemoenzymatic Synthesis of Fasamycin A
  作者：Jian Li、Hans Renata

  DOI：10.1021/acs.joc.1c00526

  日期：2021.8.20

  We report the development of a chemoenzymatic approach toward fasamycin A, a halogenated naphthacenoid that exhibits activities against methicillin-resistant Staphylococcus aureus and vancomycin-resistant Enterococcus faecalis. The synthesis was accomplished in a convergent manner: two fragments were combined together in a Sammes annulation to afford a dimethylnaphthacenone system. Finally, an enzymatic

  我们报告了针对法沙霉素 A 的化学酶学方法的发展，这是一种卤代环烷烃，对耐甲氧西林金黄色葡萄球菌和耐万古霉素粪肠球菌具有活性。合成以收敛方式完成：两个片段在 Sammes 环中组合在一起以提供二甲基萘酮系统。最后，采用酶促卤化在后期引入天然产物所需的氯取代基。
• Medicinal Flowers. XXX. Eight New Glycosides, Everlastosides F-M, from the Flowers of Helichrysum arenarium
  作者：Toshio Morikawa、Li-Bo Wang、Kiyofumi Ninomiya、Seikou Nakamura、Hisashi Matsuda、Osamu Muraoka、Li-Jun Wu、Masayuki Yoshikawa

  DOI：10.1248/cpb.57.853

  日期：——

  Eight new glycosides, everlastosides F (1), G (2), H (3), I (4), J (5), K (6), L (7), and M (8), were isolated from the methanolic extract of the flowers of Helichrysum arenarium. Their structures were elucidated on the basis of chemical and physicochemical evidence.

  从植物中分离出八种新糖苷：everlastoside F (1)、G (2)、H (3)、I (4)、J (5)、K (6)、L (7) 和 M (8)。蜡菊花的甲醇提取物。它们的结构是根据化学和物理化学证据阐明的。
• An efficient synthesis of phthalides by Diels-Alder reaction of sulfur-substituted furanones with silyloxydienes: A formal synthesis of mycophenolic acid.
  作者：Mitsuaki WATANABE、Masao TSUKAZAKI、Yumiko HAMADA、Masatomo IWAO、Sunao FURUKAWA

  DOI：10.1248/cpb.37.2948

  日期：——

  Highly substituted phthalides including a key intermediate in the synthesis of mycophenolic acid were prepared by the Diels-Alder reaction of 3-(phenylthio- or 3-(phenylsulfinyl)-2-(5H)-furanones with silyloxydienes.

  通过 3-(苯硫基或 3-(苯亚磺酰基)-2-(5H)-呋喃酮与硅氧基二烯的 Diels-Alder 反应，制备了高取代的邻苯二甲酸盐，其中包括合成霉酚酸的关键中间体。
• New Aromatic Compounds from the Fruiting Body of <i>Sparassis crispa</i> (Wulf.) and Their Inhibitory Activities on Proprotein Convertase Subtilisin/Kexin Type 9 mRNA Expression
  作者：Sunghee Bang、Hee-Sung Chae、Changyeol Lee、Hyun Gyu Choi、Jiyoung Ryu、Wei Li、Hanna Lee、Gil-Saeng Jeong、Young-Won Chin、Sang Hee Shim

  DOI：10.1021/acs.jafc.7b02657

  日期：2017.8.2

  isolation of four new aromatic compounds, sparoside A (1) and sparalides A–C (3–5), two new naturally occurring compounds, 2 and 6, and eight known compounds, 7–14. The chemical structures were determined by interpretation of nuclear magnetic resonance and mass spectrometry spectroscopic data. Extract, solvent-soluble fractions of the extract, and all of the pure compounds isolated from the fractions were

  子实体的乙酸乙酯-可溶性提取物的连续色谱绣球菌（沃尔夫）导致的四个新的芳族化合物，sPARoside A（隔离1）和sPARalides A-C（3 - 5），两个新的天然存在的化合物，2和6以及八个已知化合物7 – 14。通过解释核磁共振和质谱数据确定化学结构。提取物，提取物的溶剂可溶级分以及从这些级分中分离出的所有纯净化合物均经过前蛋白转化酶枯草杆菌蛋白酶/ kexin 9型（PCSK9）的mRNA表达测定。其中，SPAROIDE A（1），hanabiratakelide A（8），腺苷（11）和5α，6α-环氧-（22 E，24 R）-ergosta-8（14），22-二烯3β，7β-二醇（14）对PCSK9 mRNA表达表现出有效的抑制活性，IC 50值分别为20.07、7.18、18.46和8.23μM（小ber碱，阳性对照，IC 50= 8.04μM），表明化合物1，8，11
• Structure−Activity Relationships for Inhibition of Inosine Monophosphate Dehydrogenase by Nuclear Variants of Mycophenolic Acid
  作者：Peter H. Nelson、Stephen F. Carr、Bruce H. Devens、Elsie M. Eugui、Fidencio Franco、Carlos Gonzalez、Ronald C. Hawley、David G. Loughhead、David J. Milan、Eva Papp、John W. Patterson、Sussan Rouhafza、Eric B. Sjogren、David B. Smith、Rebecca A. Stephenson、Francisco X. Talamas、Ann-Marie Waltos、Robert J. Weikert、John C. Wu

  DOI：10.1021/jm9603633

  日期：1996.1.1

  Structure-activity relationships in the region of the phthalide ring of the inosine monophosphate dehydrogenase inhibitor mycophenolic acid have been explored. Replacement of the lactone ring with other cyclic moieties resulted in loss of potency, especially for larger groups. Replacement of the ring by acyclic substituents also indicated a strong sensitivity to steric bulk. A phenolic hydroxyl group, with an adjacent hydrogen bond acceptor, was found to be essential for high potency. The aromatic methyl group was essential for activity; the methoxyl group could be replaced by ethyl to give a compound with 2-4 times the potency of mycophenolic acid in vitro and in vivo.