3-(3-methyl-but-2-enyl)-1,4-dioxo-1,4-dihydro-naphthalene-2-carboxylic acid methyl ester | 78570-30-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-(3-methyl-but-2-enyl)-1,4-dioxo-1,4-dihydro-naphthalene-2-carboxylic acid methyl ester
• 英文别名: methyl 3-(3-methyl-2-butenyl)-1,4-naphthoquinone-2-carboxylate；2-methoxycarbonyl-3-prenyl-1,4-naphthoquinone；2-carbomethoxy-3-prenyl-1,4-naphthoquinone；2-Naphthalenecarboxylic acid, 1,4-dihydro-1,4-dioxo-3-(3-methyl-2-butenyl)-, methyl ester；methyl 3-(3-methylbut-2-enyl)-1,4-dioxonaphthalene-2-carboxylate
• CAS: 78570-30-6
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: RGLUQJRFDAZRRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3-methyl-but-2-enyl)-1,4-dioxo-1,4-dihydro-naphthalene-2-carboxylic acid methyl ester 在 sodium dithionite 作用下， 生成 methyl 1,4-dihydroxy-3-(3-methylbut-2-enyl)-naphthalene-2-carboxylate
  参考文献：
  名称：

  2-甲氧羰基-3-异戊烯基-1,4-萘醌，有关mollugin和蒽醌类中的生物合成的代谢物猪殃粟米草属L.

  摘要：

  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。

  DOI：

  10.1039/c39810000334
• 作为产物：
  描述：

  methyl (3-allyl-1,4-dimethoxynaphthalene-2-yl)carboxylate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) ammonium cerium(IV) nitrate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 12.25h， 生成 3-(3-methyl-but-2-enyl)-1,4-dioxo-1,4-dihydro-naphthalene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Pericyclic Reactions of Prenylated Naphthoquinones:  Biomimetic Syntheses of Mollugin and Microphyllaquinone

  摘要：

  [GRAPHICS]A total synthesis of the bioactive naphthohydroquinone mollugin and the related naphthoquinone dimer microphyllaquinone is described. Both syntheses exploit the propensity of prenylated quinones to undergo tautomerization/oxa 6 pi electrocyclizations.

  DOI：

  10.1021/ol052472u

文献信息

• 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。
• Synthesis of naturally occurring naphthoquinone epoxides and application in the synthesis of β-lapachone
  作者：Sven Claessens、Pascal Habonimana、Norbert De Kimpe

  DOI：10.1039/c004580b

  日期：——

  epoxidation protocol making use of H2O2/Na2CO3, naphthoquinone epoxides are obtained in high yields. The optimized epoxidation conditions are applied in a short and high yielding synthesis of the pharmaceutically important β-lapachone.

  提出了单烷基化和二烷基化萘醌的优化环氧化条件。基于利用H 2 O 2 /Na 2 CO 3的环氧化方案，以高收率获得萘醌环氧化物。优化的环氧化条件适用于药学上重要的短而高产的合成β-拉帕酮.
• Synthesis of the Natural Products 3-Hydroxymollugin and 3-Methoxymollugin
  作者：Mudiganti Naga Venkata Sastry、Sven Claessens、Pascal Habonimana、Norbert De Kimpe

  DOI：10.1021/jo100024b

  日期：2010.4.2

  available 3-bromomollugin 6. Surprisingly, it was found that the reaction of 3-bromomollugin 6 with sodium methoxide in methanol resulted in the formation of 3-methoxymollugin 3 and the ring-contracted methyl isopropenylfuromollugin 7. A mechanism for this ring contraction is proposed on the basis of a pericyclic retro oxa-6π ring-opening reaction. A second synthesis of 3-hydroxymollugin 2 was based on epoxidation

  3-羟基水溶蛋白2和3-甲氧基水溶蛋白3是作为毒性化合物从五倍体五味子和茜草中分离出的细胞毒性化合物。3- hydroxymollugin的合成2和3-methoxymollugin 3被开发从容易获得的3- bromomollugin开始6。出人意料地，发现3-溴联苯甲醛6与甲醇钠在甲醇中的反应导致形成3-甲氧基联苯甲醛3和环缩合的甲基异丙烯基呋喃芦丁7。。在环周逆向oxa-6π开环反应的基础上，提出了这种环收缩的机制。3-羟基软胶2的第二次合成基于3-（3-甲基丁-2-烯基）-1,4-萘醌-2-羧酸甲酯17的环氧化和随后的醌部分还原，环转化和DDQ氧化。后者的氧化过程导致3-羟基软糖2以及重排的呋喃青霉素4，这是天然产物mollugin 1的环状缩合类似物。
• Pericyclic Reactions of Prenylated Naphthoquinones:  Biomimetic Syntheses of Mollugin and Microphyllaquinone
  作者：Jean-Philip Lumb、Dirk Trauner

  DOI：10.1021/ol052472u

  日期：2005.12.1

  [GRAPHICS]A total synthesis of the bioactive naphthohydroquinone mollugin and the related naphthoquinone dimer microphyllaquinone is described. Both syntheses exploit the propensity of prenylated quinones to undergo tautomerization/oxa 6 pi electrocyclizations.