(3Z)-7-methoxy-3-[(3,4-dimethoxyphenyl)methylene]-1(3H)-isobenzofuranone | 147666-87-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: (3Z)-7-methoxy-3-[(3,4-dimethoxyphenyl)methylene]-1(3H)-isobenzofuranone
• 英文别名: (Z)-3-(3,4-dimethoxybenzylidene)-7-methoxyisobenzofuran-1(3H)-one；3-(3,4-dimethoxybenzylidene)-7-methoxy-2-benzofuran-1(3H)-one；(3Z)-3-[(3,4-dimethoxyphenyl)methylidene]-7-methoxy-2-benzofuran-1-one
• CAS: 147666-87-3
• 化学式: C₁₈H₁₆O₅
• 分子量: 312.322
• InChiKey: PXQRIFQWIIJYJG-DHDCSXOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3Z)-7-methoxy-3-[(3,4-dimethoxyphenyl)methylene]-1(3H)-isobenzofuranone 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以97%的产率得到(3Z)-3-[(3,4-二羟基苯基)亚甲基]-7-羟基-2-苯并呋喃-1-酮
  参考文献：
  名称：

  苯甲酸和乙烯基芳烃的无配位钯催化氧化偶联一步合成异香豆素和3-苄叉二苯酞

  摘要：

  已开发出一种简单的合成方法，可通过C–H烯化反应和易得的苯甲酸与乙烯基芳烃的氧化偶联来制备异香豆素和3-亚苄基苯。取代基对苯甲酸的直接作用允许以纯净形式合成两种类型的内酯。

  DOI：

  10.1021/jo400174w
• 作为产物：
  描述：

  3-[(3,4-dimethoxyphenyl)-methoxymethyl]-7-methoxy-3H-2-benzofuran-1-one 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 12.0h， 以61.5%的产率得到(3Z)-7-methoxy-3-[(3,4-dimethoxyphenyl)methylene]-1(3H)-isobenzofuranone
  参考文献：
  名称：

  Development of Bioactive Functions in Hydrangeae Dulcis Folium. VI. Syntheses of Thunberginols A and F and Their 3'-Deoxy-Derivatives Using Regiospecific Lactonization of Stilbene Carboxylic Acid: Structures and Inhibitory Activity on Histamine Release of Hydramacrophyllols A and B.

  摘要：

  氯化铜（II）介导的 2-羧基二苯乙烯的内酯化反应进行了区域特异性反应，生成了五元内酯，而使用 N-溴代琥珀酰亚胺和阳极氧化进行的溴内酯化反应则生成了六元内酯。利用这些区域特异性内酯化反应作为关键步骤，从phyllodulcin 和 hydrangenol 合成了抗过敏和抗菌的异香豆素和苯亚甲基酞thunberginols A 和 F 及其 3'-deoxyanalogs 。根据物理化学和化学证据，从绣线菊叶中分离出了两种名为水飞蓟醇 A 和 B 的邻苯二甲酸盐，并确定了它们的立体结构，其中包括应用氯化铜（II）内酯化法从水飞蓟醇合成了水飞蓟醇 A 和 B。此外，还发现水合麦考酚 A 和 B 对抗原-抗体反应诱导的大鼠腹腔渗出细胞释放组胺具有抑制作用。

  DOI：

  10.1248/cpb.44.1890

文献信息

• Synthesis of 3-Substituted Isocoumarins and Their Inhibitory Effects on Degranulation of RBL-2H3 Cells Induced by Antigen
  作者：Ai Kurume、Yasuhiro Kamata、Masayuki Yamashita、Qilong Wang、Hisashi Matsuda、Masayuki Yoshikawa、Ikuo Kawasaki、Shunsaku Ohta

  DOI：10.1248/cpb.56.1264

  日期：——

  Eleven 3-substituted isocoumarins and a benzylidenephthalide were synthesized through thermal cyclization reaction of δ- and γ-ketoamides, respectively. Subsequent deprotection of the hydroxyl groups of the resulting isocoumarin and benzylidenephthalide compounds afforded thunberginols A, B, and F, respectively, which originated from the processed leaves of Hydrangea macrophylla SERINGE var. thunbergii MAKINO. The synthesized isocoumarins and thunberginols were evaluated for their anti-allergic activity, in which thunberginol B exhibited the highest inhibitory potency on the degranulation of RBL-2H3 cells induced by antigen. Structure–activity relationship studies were carried out to determine the necessary substituents on the 3-phenylisocoumarin skeleton for inhibitory activity.

  合成了十一种3-取代异香豆素和一个苄叉邻苯二甲酸酯，这些化合物分别通过δ-和γ-酮酰胺的热环化反应得到。随后的去保护反应使得所得的异香豆素和苄叉邻苯二甲酸酯化合物分别获得了来自紫阳花（Hydrangea macrophylla SERINGE var. thunbergii MAKINO）加工叶子的thunberginols A、B和F。合成的异香豆素和thunberginols被评估其抗过敏活性，其中thunberginol B对抗原诱导的RBL-2H3细胞去颗粒化展现了最高的抑制效力。进行了结构—活性关系研究，以确定3-苯基异香豆素骨架上抑制活性所需的取代基。
• Synthesis of 3-substituted isocoumarins and related natural products.
  作者：Shunsaku OHTA、Yasuhiro KAMATA、Takayo INAGAKI、Yukari MASUDA、Satoshi YAMAMOTO、Masayuki YAMASHITA、Ikuo KAWASAKI

  DOI：10.1248/cpb.41.1188

  日期：——

  Several N, N-diethyl-2-acylmethylbenzamides (6) were prepared from N, N-diethyl-2-toluamides (4), and the ketoamides (6) were easily cyclized to the corresponding 3-substituted isocoumarins (8) by heating in acetic acid or xylene. This simple procedure was applied to the synthesis of thunberginol A (1), thunberginol B (2), thunberginol F (14), and a key-intermediate (8j) for achlisocoumarin I (3).

  几种N,N-二乙基-2-酰基甲基苯胺（6）是从N,N-二乙基-2-甲苯酰胺（4）制备而成的，这些酮胺（6）可以通过在醋酸或二甲苯中加热轻松环化为相应的3取代异香豆素（8）。这一简单的步骤被应用于青藏醇A（1）、青藏醇B（2）、青藏醇F（14）以及达克异香豆素I（3）的一个关键中间体（8j）的合成。
• Chemical Transformation from Dihydroisocoumarin into Benzylidenephthalide by Use of Regiospecific Oxidative Lactonization Mediated by Copper Chloride(II). Syntheses of Thunberginol F and Hydramacrophyllol A and B.
  作者：Masayuki YOSHIKAWA、Emiko HARADA、Nobuhiro YAGI、Yasuhiro OKUNO、Osamu MURAOKA、Hiroshi AOYAMA、Nobutoshi MURAKAMI

  DOI：10.1248/cpb.42.721

  日期：——

  Oxidative lactonization of 2-carboxystilbene mediated by CuCl2 proceeded regiospecifically to give the five-membered lactone. By utilizing this lactonization as a key reaction, chemical transformation from dihydroisocoumarine into benzylidenephthalide was accomplished, and it was applied to structural elucidation of two new phthalide, hydramacrophyllols A and B.

  CuCl2 介导的 2-羧基二苯乙烯的氧化内酯化反应进行区域特异性，得到五元内酯。利用该内酯化反应作为关键反应，完成了从二氢异香豆素到亚苄基苯酞的化学转化，并将其应用于两种新的苯酞——Hydrmacrophyllols A和B的结构解析。
• Development of Bioactive Functions in Hydrangeae Dulcis Folium. III. On the Antiallergic and Antimicrobial Principles of Hydrangeae Dulcis Folium. (1). Thunberginols A, B, and F.
  作者：Masayuki YOSHIKAWA、Emiko HARADA、Yoshikazu NAITOH、Kimiyo INOUE、Hisashi MATSUDA、Hiroshi SHIMODA、Johji YAMAHARA、Nobutoshi MURAKAMI

  DOI：10.1248/cpb.42.2225

  日期：——

  From the less polar fraction of Hydrangeae Dulcis Folium, the fermented and dired leaves of Hydrangea macrophylla SERINGE var. thunbergii MAKINO, eight antiallergic and antimicrobial principles were isolated together with several known compounds. Among the newly isolated bioactive constituents, the chemical structures of thunberginols A, B, and F have been determined on the basis of chemical and physicochemical evidence. Thunberginols A, B, and F were found to exhibit more potent antiallergic activity than phyllodulcin, hydrangenol, disodium cromoglycate (DSCG), and tranilast. In addition, these thunberginols showed antimicrobial activity against oral bacteria.

  从大绣球花（Hydrangea macrophylla SERINGE var. thunbergii MAKINO）的发酵和干燥叶片 Hydrangeae Dulcis Folium 中极性较弱的部分中，分离出了八种抗过敏和抗菌成分以及几种已知化合物。在新分离出的生物活性成分中，根据化学和物理化学证据确定了绣线菊醇 A、B 和 F 的化学结构。研究发现，松柏醇 A、B 和 F 的抗过敏活性比植物多糖、海兰根醇、色甘酸二钠（DSCG）和氨苯蝶啶更强。此外，这些琥珀精醇还对口腔细菌具有抗菌活性。
• Thunberginols A, B, and F, new antiallergic and antimicrobial principles from Hydrangeae Dulcis Folium.
  作者：Masayuki YOSHIKAWA、Emiko UCHIDA、Nobuyasu CHATANI、Nobutoshi MURAKAMI、Johji YAMAHARA

  DOI：10.1248/cpb.40.3121

  日期：——

  Six new antiallergic and antimicrobial principles, thunberginols A, B, C, D, E, and F, were isolated from Hydrangeae Dulcis Folium, the fermented and dried leaves of Hydrangea macrophylla SERINGE var. thunbergii MAKINO. The chemical structures of thunberginols A, B, and F have been determined on the basis of chemical and physicochemical evidence. Thunberginols A, B, and F showed more potent antiallergic activity than phyllodulcin, hydrangenol, and AA-861 in the in vitro test using the Schults-Dale reaction in sensitized guinea pig bronchial muscle. Thunberginols A, B, and F also exhibited antimicrobial activity against oral bacteria.

  从绣球花（Hydrangeae Dulcis Folium）中分离出六种新的抗过敏和抗菌成分，即绣球素A、B、C、D、E和F，绣球花（Hydrangea macrophylla SERINGE var. thunbergii MAKINO）是绣球花（Hydrangea macrophylla）的发酵干燥叶子。根据化学和物理化学证据，确定了绣球素A、B和F的化学结构。在体外测试中，使用Schults-Dale反应对豚鼠支气管肌肉进行敏化，结果表明，绣球素A、B和F比叶绣球素、绣球素和AA-861具有更强的抗过敏活性。绣球素A、B和F还对口腔细菌具有抗菌活性。