(+/-)-7-Hydroxy-2-isopropenyl-2,3-dihydronaphtho[1,2-b]furan-4,5-dione | 721443-90-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: (+/-)-7-Hydroxy-2-isopropenyl-2,3-dihydronaphtho[1,2-b]furan-4,5-dione
• 英文别名: (±)-7-hydroxy-2-isopropenyl-2,3-dihydronaphtho[1,2-b]furan-4,5-dione；racemic lantalucratin C；(±)-lantalucratin C；Lantalucratin C；7-hydroxy-2-prop-1-en-2-yl-2,3-dihydrobenzo[g][1]benzofuran-4,5-dione
• CAS: 721443-90-9
• 化学式: C₁₅H₁₂O₄
• 分子量: 256.258
• InChiKey: RFNIZIGETMKYEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-methyl-1-(1,3,4-trimethoxy-6-methoxymethoxy-2-naphthalenyl)-but-3-en-2-ol 在 ammonium cerium (IV) nitrate 、 sodium hydrogen sulfate 、 silica gel 作用下， 以 水 、 乙腈 、 二氯甲烷 为溶剂， 反应 5.5h， 以64%的产率得到(+/-)-7-Hydroxy-2-isopropenyl-2,3-dihydronaphtho[1,2-b]furan-4,5-dione
  参考文献：
  名称：

  利用烷氧基甲基氯对2-羟基-1,4-萘醌衍生物进行非常规的化学选择性醚化：范围，机理和在合成具有生物活性的天然产物（±）-lantalucratin C中的应用

  摘要：

  描述了2-羟基-1，4-萘醌衍生物与烷氧基烷基氯化物和氢化物碱的新型醚化。对条件和底物范围的精确研究表明，该反应特别发生在具有2-羟基-1,4-苯醌骨架的分子中。实现了化学选择性的O-甲基化反应，以提供合成上重要的中间体，该中间体可轻松获得具有抗肿瘤活性的天然产物。

  DOI：

  10.1016/j.tet.2016.01.040

文献信息

• The first enantioselective total synthesis of lantalucratin C and determination of its absolute configuration
  作者：Tokutaro Ogata、Manami Tanaka、Momoe Ishigaki、Maki Shimizu、Arisa Nishiuchi、Kiyofumi Inamoto、Tetsutaro Kimachi

  DOI：10.1016/j.tet.2015.07.050

  日期：2015.9

  Described here is the first enantioselective total synthesis of lantalucratin C, which was isolated from the rainforest plant Lantana involucrata, and which possesses anti-tumor activity. The OH group on the aromatic ring was systematically introduced by an appropriate management of the OH protecting groups. The alkyl side chain connected to a chiral carbon center was incorporated by directed ortho-lithiation

  此处描述的是从雨林植物马Lan丹（Lantana involucrata）中分离出来的兰塔卢卡汀C的第一个对映选择性全合成，并具有抗肿瘤活性。芳香环上的OH基是通过适当管理OH保护基而系统地引入的。通过萘的定向邻位锂化，然后不对称环氧化，并入连接到手性碳中心的烷基侧链。通过CAN介导的氧化环化反应，由3-羟基烷基萘构建呋喃基1,2-萘醌骨架。通过Kusumi-Mosher方法将C2碳上的绝对立体化学分配为R-构型。
• Pharmaceutical Composition for the Treatment or Prevention of Diseases Involving Obesity, Diabetes, Metabolic Syndrome, Neuro-Degenerative Diseases and Mitochondria Dyfunction Diseases
  申请人：Yoo Sang-Ku

  公开号：US20080146655A1

  公开（公告）日：2008-06-19

  Provided is a pharmaceutical composition for the treatment and prevention of obesity, diabetes, metabolic syndromes, degenerative diseases and mitochondrial dysfunction-related diseases, comprising: a therapeutically effective amount of a compound represented by Formula I below, or a pharmaceutically acceptable salt, prodrug, solvate or isomer thereof, and a pharmaceutically acceptable carrier, a diluent or an excipient, or any combination thereof.

  提供一种药物组合物，用于治疗和预防肥胖、糖尿病、代谢综合征、退行性疾病和线粒体功能障碍相关疾病，包括：以下式I所表示的化合物的治疗有效量，或其药学上可接受的盐、前药、溶剂或异构体，以及药学上可接受的载体、稀释剂或赋形剂，或其任意组合。
• PHARMACEUTICAL COMPOSITION FOR THE TREATMENT OR PREVENTION OF DISEASES INVOLVING OBESITY, DIABETES, METABOLIC SYNDROME, NEURO-DEGENERATIVE DISEASES AND MITOCHONDRIA DYSFUNCTION DISEASES
  申请人：Yoo Sang-Ku

  公开号：US20090292011A1

  公开（公告）日：2009-11-26

  Provided is a pharmaceutical composition for the treatment and prevention of obesity, diabetes, metabolic syndromes, degenerative diseases and mitochondrial dysfunction-related diseases, comprising: a therapeutically effective amount of a compound represented by Formula I below, or a pharmaceutically acceptable salt, prodrug, solvate or isomer thereof, and a pharmaceutically acceptable carrier, a diluent or an excipient, or any combination thereof.

  提供了一种用于治疗和预防肥胖、糖尿病、代谢综合征、退行性疾病以及线粒体功能障碍相关疾病的制药组合物，包含以下公式I所表示的化合物的治疗有效量，或其药学上可接受的盐、前药、溶剂或异构体，以及药学上可接受的载体、稀释剂或赋形剂，或任何组合。
• NOVEL PHENANTHRENEQUINONE-BASED COMPOUND AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME FOR THE TREATMENT OR PREVENTION OF DISEASE INVOLVING METABOLIC SYNDROME
  申请人：Yoo Sang-Ku

  公开号：US20100137422A1

  公开（公告）日：2010-06-03

  Provided is a pharmaceutical composition for the treatment and/or prevention of disease involving metabolic syndromes, comprising (a) a therapeutically effective amount of a particular compound represented by Formula 1 as defined in the specification, or isomer, prodrug, or solvate or thereof, and (b) a pharmaceutically acceptable carrier, a diluent or an excipient, or any combination thereof.

  提供了一种用于治疗和/或预防涉及代谢综合征的疾病的制药组合物，包括(a)根据规范中定义的公式1所代表的特定化合物的治疗有效量，或其异构体，前药或溶剂或其任意组合物，以及(b)药学上可接受的载体，稀释剂或赋形剂，或其任意组合物。
• Pharmaceutical composition for obesity, diabetes, metabolic syndrome, neuro-degenerative diseases and mitochondria dysfunction diseases
  申请人：Md Bioalpha Co., Ltd.

  公开号：EP2532390A2

  公开（公告）日：2012-12-12

  Provided is a pharmaceutical composition for the treatment and prevention of obesity, diabetes, metabolic syndromes, degenerative diseases and mitochondrial dysfunction-related diseases, comprising: a therapeutically effective amount of a compound represented by Formula I below, or a pharmaceutically acceptable salt, prodrug, solvate or isomer thereof, and a pharmaceutically acceptable carrier, a diluent or an excipient, or any combination thereof.

  本发明提供了一种用于治疗和预防肥胖症、糖尿病、代谢综合征、退行性疾病和线粒体功能障碍相关疾病的药物组合物，该药物组合物包含：治疗有效量的下式 I 所代表的化合物，或其药学上可接受的盐、原药、溶媒或异构体，以及药学上可接受的载体、稀释剂或赋形剂，或其任意组合。

表征谱图