二氢大叶茜草素 | 60657-93-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 中文名称: 二氢大叶茜草素
• 英文名称: methyl 6-hydroxy-2,2-dimethyl-3,4-dihydro-2H-benzo-[h]chromene-5-carboxylate
• 英文别名: methyl 6-hydroxy-2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromen-5-carboxylate；4-hydroxy-3-carbomethoxynaphtho[1,2-b]-3',3'-dimethylpyran；3,4-dihydromoullugin；3,4-dihydromollugin；dihydromollugin；6-hydroxy-2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5-carboxylic acid methyl ester；methyl 6-hydroxy-2,2-dimethyl-3,4-dihydrobenzo[h]chromene-5-carboxylate
• CAS: 60657-93-4
• 化学式: C₁₇H₁₈O₄
• 分子量: 286.328
• InChiKey: AKPYYGWMASCNAF-UHFFFAOYSA-N

物化性质

• 熔点：
  96-97 °C
• 沸点：
  448.2±45.0 °C(Predicted)
• 密度：
  1.212±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 储存条件：
  存储条件：2-8°C，干燥且密封。

制备方法与用途

二氢莫鲁金是一种天然的萘酸酯。

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	methyl 1,4-dihydroxy-3-(3-methylbut-2-enyl)-naphthalene-2-carboxylate	78570-31-7	C17H18O4	286.328
  大叶茜草素	mollugin	55481-88-4	C17H16O4	284.312
  ——	nordihydrolapachenol	18865-37-7	C15H16O2	228.291

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	methyl 6-methoxy-2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5-carboxylate	——	C18H20O4	300.354
  大叶茜草素	mollugin	55481-88-4	C17H16O4	284.312

反应信息

• 作为反应物：
  描述：

  二氢大叶茜草素 在 二甲基二环氧乙烷 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 水 、 丙酮 、 甲苯 为溶剂， 反应 3.0h， 生成 trans-3,4-dihydroxy-3,4-dihydromollugin
  参考文献：
  名称：

  Efficient one-pot trans-dihydroxylation of 2H-pyrans using dimethyldioxirane (DMD): synthesis of trans-3,4-dihydroxy-3,4-dihydro-O-methyloctandreolones, orixalone D, and trans-3,4-dihydroxy-3,4-dihydromollugin natural products

  摘要：

  An efficient one-pot formation of trans-diols on 2H-pyranyl rings was achieved by dimethyldioxirane in wet acetone. This new methodology was applied to the synthesis of natural products containing trans-diol on the pyranyl rings such as trans-3,4-dihydroxy-3,4-dihydro-0-methyloctandreolones, orixalone D, and trans-3,4-dihydroxy-3,4-dihydromollugin. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.07.022
• 作为产物：
  描述：

  1,4-二羟基萘 在 18-冠醚-6 、 silver trifluoromethanesulfonate 、 potassium hydride 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 14.17h， 生成 二氢大叶茜草素
  参考文献：
  名称：

  Facile Synthesis of Mollugin by Kinetic Control and anti-HCV (Hepatitis C Virus) Activity of Its Analogues

  摘要：

  据报道，Mollugin具有多种生物活性，包括抗肿瘤、抗病毒（针对乙型肝炎病毒）、抗衰老和抗突变活性。本文介绍了一种从廉价的起始原料1,4-萘醌出发，通过动力学控制，两步高效简洁合成Mollugin的方法，并筛选了所制备的Mollugin衍生物对丙型肝炎病毒（HCV）的抑制能力。研究表明，二氢苯并色原烯结构可能作为一种新的领先化合物，成为额外的抗HCV药物。

  DOI：

  10.5012/bkcs.2014.35.11.3232

文献信息

• 몰루긴 유도체 화합물, 이의 광학이성질체, 또는 이의 약학적으로 허용 가능한 염, 및 이를 유효성분으로 포함하는 염증성 장질환의 예방 또는 치료용 약학 조성물
  申请人：KOREA PHARMA CO., LTD. 주식회사한국파마(119980043604) Corp. No ▼ 180111-0059112BRN ▼124-81-15899

  公开号：KR20170122970A

  公开（公告）日：2017-11-07

  본 발명은 몰루긴 유도체 화합물, 이의 광학이성질체, 또는 이의 약학적으로 허용 가능한 염, 및 이를 유효성분으로 포함하는 염증성 장질환의 예방 또는 치료용 약학 조성물에 관한 것이다. 본 발명의 몰루긴 유도체 화합물은 아민그룹의 도입을 통해 염(salt)화가 용이하여 기존의 난용성 물질인 몰루긴에 비해 용해도 개선효과가 현저할 뿐만 아니라, 상기 몰루긴 유도체 화합물을 처리하는 경우 TNF-α 또는 IL-6 유도성 HT-29 세포에서 단핵구 세포인 U937 세포의 부착을 억제하는 활성이 우수하여, 염증성 장질환의 예방 또는 치료용 약학 조성물로 유용하게 사용될 수 있다.

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• Biosynthesis of anthraquinones and related compounds in Galium mollugo cell suspension cultures
  作者：Kenichiro Inoue、Yoshinori Shiobara、Hidekazu Nayeshiro、Hiroyuki Inouye、Graham Wilson、Meinhart H. Zenk

  DOI：10.1016/s0031-9422(00)80323-4

  日期：1984.1

  Abstract From Galium mollugo cell suspension cultures, 1,4-dihydroxy-3-prenyl-2-naphtholic acid methyl ester diglucoside was isolated along with anthraquinones and mollugin. Production of the diglucoside was much increased by administering 2-succinylbenzoate to the cultures. The incorporation of 2-succinylbenzoate into lucidin-3-primeveroside, mollugin and the diglucoside in the mode so far proposed

  摘要 从 Galium mollugo 细胞悬浮培养物中分离出 1,4-dihydroxy-3-prenyl-2-naphtholic acid 甲酯二葡糖苷以及蒽醌和 mollugin。通过向培养物中施用 2-琥珀酰苯甲酸酯，二葡糖苷的产量大大增加。通过向细胞培养物中施用 13C 标记的 2-琥珀酰苯甲酸酯，证实了 2-琥珀酰苯甲酸酯以迄今为止为红宝石蒽醌提出的模式掺入 lucidin-3-primeveroside、mollugin 和二葡糖苷中。
• Efficient Syntheses of Mollugin
  作者：Norbert De Kimpe、Pascal Habonimana、Sven Claessens

  DOI：10.1055/s-2006-950441

  日期：2006.9

  Two different strategies are presented to synthesize mollugin, based upon a close investigation of possible natural precursors. The best total synthesis of mollugin, a natural product isolated from rubiaceous herbs, is achieved in an overall yield of 61% starting from 1,4-dihydroxynaphthalene-2-carboxylic acid. The key reaction is the prenylation and spontaneous pyran ring formation. Subsequent oxidation of the intermediate 3,4-dihydromollugin with DDQ afforded mollugin.

  在对可能的天然前体进行仔细研究的基础上，提出了两种不同的合成莫卢金的方法。莫卢金是从茜草科植物中分离出的天然产物，从1,4-二羟基萘-2-羧酸开始，以61%的总收率实现了莫卢金的最佳全合成。关键反应是萜烯化和吡喃环的自发形成。随后用DDQ氧化中间产物3,4-二氢莫卢金，得到莫卢金。
• 2-Methoxycarbonyl-3-prenyl-1,4-naphthoquinone, a metabolite related to the biosynthesis of mollugin and anthraquinones in Galium mollugo L.
  作者：Lutz Heide、Eckhard Leistner

  DOI：10.1039/c39810000334

  日期：——

  The structure of 2-methoxycarbonyl-3-prenyl-1,4-naphthoquinone, isolated from Galium mollugo plants, has been elucidated by spectroscopic methods, synthesis, and derivatisation.

  从分贝Gal植物中分离得到的2-甲氧基羰基-3-异戊烯基-1,4-萘醌的结构已经通过光谱方法，合成和衍生化进行了阐明。
• Synthesis of Naturally Occurring Rubilactone, Mollugin, and Dihydromollugin of<i>Rubia cordifolia</i>
  作者：Li-Kang Ho、Hsi-Jung Yu、Chen-Ta Ho、Ming-Jaw Don

  DOI：10.1002/jccs.200100014

  日期：2001.2

  Rubilactone (1), dihydromollugin (2), and mollugin (3) are naturally occurring products found in Rubia cordifolia, which is a famous Chinese herb with anti tumor, viral inhibition and other activities. Synthetic studies were carried out in these naphthoic acid esters starting from 1,4-dihydroxy-2-naphthoic acid. In this study, we finished the synthesis of rubilactone which has not been reported before

  Rubilactone (1)、dihydromollugin (2) 和 mollugin (3) 是天然存在于茜草中的产物，茜草是著名的中草药，具有抗肿瘤、抑制病毒等活性。从1,4-二羟基-2-萘甲酸开始对这些萘甲酸酯进行合成研究。在这项研究中，我们完成了以前未报道过的鲁比内酯的合成，并且与文献中报道的方法相比，还通过不同的方法合成了产率更高的二氢莫鲁金和莫鲁金。