(E)-2-(3,7-dimethylocta-2,6-dien-1-yl)naphthalene-1,4-dione | 4966-05-6

• 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: (E)-2-(3,7-dimethylocta-2,6-dien-1-yl)naphthalene-1,4-dione
• 英文别名: (E)-2-(3,7-dimethylocta-2,6-dienyl)-1,4-naphthoquinone；(E)-2-[3,7-dimethylocta-2,6-dienyl]-1,4-naphthoquinone；2-geranyl-1,4-naphthoquinone；2-geranyl-[1,4]naphthoquinone；2-Geranyl-[1,4]naphthochinon；2-[(2'E)-3',7'-dimethyl-2',6'-octadienyl]-1,4-naphthoquinone；2-[(2E)-3,7-dimethylocta-2,6-dienyl]naphthalene-1,4-dione
• CAS: 4966-05-6
• 化学式: C₂₀H₂₂O₂
• 分子量: 294.393
• InChiKey: WALCBDVYDNDULV-RVDMUPIBSA-N

物化性质

• 沸点：
  439.5±45.0 °C(predicted)
• 密度：
  1.062±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,4-二羟基萘 、 香叶醇 在 1,4-二氧六环 、 草酸 作用下， 生成 (E)-2-(3,7-dimethylocta-2,6-dien-1-yl)naphthalene-1,4-dione
  参考文献：
  名称：

  Extensions of the Vitamin K₁ Synthesis

  摘要：

  DOI：

  10.1021/ja01867a065

文献信息

• Synthesis of Vitamin K and Related Naphthoquinones via Demethoxycarbonylative Annulations and a Retro-Wittig Rearrangement
  作者：Dipakranjan Mal、Ketaki Ghosh、Supriti Jana

  DOI：10.1021/acs.orglett.5b02920

  日期：2015.12.4

  Anionic annulations of 3-nucleofugal phthalides with α-alkyl(aryl)acrylates involving a demethoxycarbonylation provide a succinct synthesis of vitamin K and related naphthoquinones. Also reported is a new cascade reaction stemming from a Cope–retro-Wittig rearrangement. This cascade leads to direct formation of 1-hydroxy-4-prenyloxynaphthalene-2-carboxylates from the corresponding α-prenyl acrylate

  3-核真菌邻苯二甲酸酯与α-烷基（芳基）丙烯酸酯的阴离子环化涉及脱甲氧基羰基化，可简捷地合成维生素K和相关的萘醌。还报道了源自Cope-retro-Wittig重排的新的级联反应。该级联导致由相应的α-异戊烯基丙烯酸酯受体直接形成1-羟基-4-异戊烯氧基萘-2-羧酸酯。
• 2-Geranyl-1,4-naphthoquinone, a Possible Intermediate of Anthraquinones in a<i>Sesamum indicum</i>Hairy Root Culture
  作者：Toshio FURUMOTO、Tomoko OHARA、Tetsuya KUBO、Yasuhiro KAWANAMI、Hiroshi FUKUI

  DOI：10.1271/bbb.70352

  日期：2007.10.23

  2-Geranyl-1,4-naphthoquinone was isolated from the hairy root culture of Sesamum indicum. The structure was determined to be 2-[(E)-3,7-dimethylocta-2,6-dienyl]-1,4-naphthoquinone on the basis of spectroscopic evidence and chemical synthesis. The production of anthrasesamones A, B and C by the hairy root culture was also confirmed for the first time.

  从 Sesamum indicum 的毛根培养物中分离出了 2-香叶基-1,4-萘醌。根据光谱证据和化学合成，确定其结构为 2-[(E)-3,7-二甲基辛-2,6-二烯基]-1,4-萘醌。此外，还首次证实了发根培养物能产生蒽酮酰胺 A、B 和 C。
• Allylation of quinones by allylic indium reagents
  作者：Shuki Araki、Nobuhito Katsumura、Yasuo Butsugan

  DOI：10.1016/0022-328x(91)83277-b

  日期：1991.9

  sigmatropic rearrangement. Substituted quinones reacted with allylindium reagent giving excellent yields of allyquinols, whereas with prenylindium and geranylindium reagents, trisubstituted quinones gave diprenylcyclohexene-1,4-diones and 2,3-disubstituted quinones gave mixtures of prenylhydroquinones and diprenylcyclohexene-1,4-diones. In the prenylation of haloquinones, 1,2-addition, [3,3] sigmatropic rearrangement

  研究了烯丙基倍半卤化物对各种醌的烯丙基化作用。未取代的p的反应苯甲酸醌与烯丙基，pre烯丙基和香叶菊醇试剂在用氧化银氧化后，以良好的收率得到相应的烯丙基化的醌。这些反应似乎是通过在γ-碳上添加1,2-烯丙基铟试剂然后进行[3,3]σ重排而进行的。取代的醌与烯丙基dium试剂反应可得到优异的烯丙基醇收率，而与戊炔醇和ger草醇dium试剂反应，三取代醌可生成二戊烯基环己烯-1,4-二酮，2,3-二取代醌可得到异戊二烯基氢醌和二戊烯基环己烯-1,4-二酮的混合物。在卤代醌的异戊烯基化中，依次产生1,2-加成，[3,3]σ重排和消除铟（III）卤化物，生成异戊烯基醌。2-羟基和2-甲氧基-1，
• Preparation process of quinone derivative and intermediate for the preparation thereof
  申请人：EISAI CHEMICAL CO., LTD.

  公开号：EP0613877A1

  公开（公告）日：1994-09-07

  Disclosed herein is a process for the preparation of a quinone derivative represented by the following formula: wherein R¹ and R² are identical with or different from each other and mean individually a lower alkyl or lower alkoxy group, or may form an aromatic ring together, R³ denotes a lower alkyl group, n stands for 0 or an integer of 1-9, and a linkage --- is a single or double bond, such as a vitamin K derivative or coenzyme Q derivative, in high yields without forming any geometric isomer, wherein a Retro Diels-Alder reaction is employed, as well as a 1,4,4a,8a-tetrahydro-4aα-alkenyl-1α,4α-methanonaphthalene-5,8-dione derivative which is useful as an intermediate for the preparation of the quinone derivative.

  本文公开了一种制备下式所代表的醌衍生物的工艺： 其中R¹和R²彼此相同或不同，分别指低级烷基或低级烷氧基，或可共同形成芳香环，R³表示低级烷基，n代表0或1-9的整数，连接-----是单键或双键、在采用 Retro Diels-Alder 反应的情况下，可以高产率地制备维生素 K 衍生物或辅酶 Q 衍生物，而不会形成任何几何异构体；还可以制备 1,4,4a,8a-四氢-4aα-烯基-1α,4α-甲桥萘-5,8-二酮衍生物，该衍生物可用作制备醌衍生物的中间体。
• Probe compound for detecting and isolating enzymes and means and methods using the same
  申请人：Helmholtz-Zentrum für Infektionsforschung GmbH

  公开号：EP2230312A1

  公开（公告）日：2010-09-22

  The present invention relates to a probe compound that can comprise any substrate or metabolite of an enzymatic reaction in addition to an indicator component, such as, for example, a fluorescence dye, or the like. Moreover, the present invention relates to means for detecting enzymes in form of an array, which comprises any number of probe compounds of the invention which each comprise a different metabolite of interconnected metabolites representing the central pathways in all forms of life. Moreover, the present invention relates to a method for detecting enzymes involving the application of cell extracts or the like to the array of the invention which leads to reproducible enzymatic reactions with the substrates. These specific enzymatic reactions trigger the indicator (e.g. a fluorescence signal) and bind the enzymes to the respective cognate substrates. Moreover, the invention relates to means for isolating enzymes in form of nanoparticles coated with the probe compound of the invention. The immobilisation of the cognate substrates or metabolites on the surface of nanoparticles by means of the probe compounds allows capturing and isolating the respective enzyme, e.g. for subsequent sequencing.

  本发明涉及一种探针化合物，它可以包括酶反应的任何底物或代谢物，此外还包括指示成分，例如荧光染料或类似物。此外，本发明还涉及以阵列形式检测酶的方法，该阵列由任意数量的本发明探针化合物组成，每种探针化合物由代表所有生命形式中中心途径的相互关联的代谢物中的不同代谢物组成。此外，本发明还涉及一种检测酶的方法，该方法涉及将细胞提取物或类似物应用于本发明的阵列，从而导致与底物发生可重复的酶反应。这些特定的酶反应会触发指示剂（如荧光信号），并将酶与各自的同源底物结合。此外，本发明还涉及以涂覆有本发明探针化合物的纳米颗粒形式分离酶的方法。通过探针化合物将同源底物或代谢物固定在纳米颗粒表面，可以捕获和分离相应的酶，例如用于后续测序。