2,3-dihydroxy-chromeno[5',4',3':3,4,5]chromeno[7,8-b]quinoxaline-5,14-dione | 18463-81-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2,3-dihydroxy-chromeno[5',4',3':3,4,5]chromeno[7,8-b]quinoxaline-5,14-dione
• 英文别名: 2,3-dihydroxy-chromeno[5',4',3':3,4,5]chromeno[7,8-b]quinoxaline-5,14-dione
• CAS: 18463-81-5
• 化学式: C₂₀H₈N₂O₆
• 分子量: 372.293
• InChiKey: FBYHHGQBUKXFHT-UHFFFAOYSA-N

物化性质

• 沸点：
  798.6±60.0 °C(predicted)
• 密度：
  1.824±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  28.0
• 可旋转键数：
  0.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  126.66
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2,3-dihydroxy-chromeno[5',4',3':3,4,5]chromeno[7,8-b]quinoxaline-5,14-dione 生成 euphorbin A-phenazine
  参考文献：
  名称：

  YOSHIDA, TAKASHI;CHEN, LING;SHINGU, TETSURO;OKUDA, TAKUO, CHEM. AND PHARM. BULL., 36,(1988) N 8, C. 2940-2949

  摘要：

  DOI：
• 作为产物：
  描述：

  没食子酸甲酯 在 邻四氯苯醌 作用下， 以 甲醇 、 乙醚 、 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 30.0h， 生成 2,3-dihydroxy-chromeno[5',4',3':3,4,5]chromeno[7,8-b]quinoxaline-5,14-dione
  参考文献：
  名称：

  Ellagitannin Chemistry. The First Synthesis of Dehydrohexahydroxydiphenoate Esters from Oxidative Coupling of Unetherified Methyl Gallate

  摘要：

  A simple o-chloranil-mediated oxidative dimerization of methyl gallate in anhydrous ether furnishes a dimethyl dehydrohexahydroxydiphenoate (DHHDP) product as a pale yellow precipitate in good yield. This methyl gallate dehydrodimer rapidly rearranges in acetone to give a mixture of two additional DHHDP regioisomers. One of these species corresponds to the isomer of the dehydrohexahydroxydiphenoyl group commonly observed in dehydroellagitannin natural products. Sodium dithionite-mediated reduction of the initially formed dimethyl dehydrohexahydroxydiphenoate and/or its derived regioisomers efficiently furnishes dimethyl hexahydroxydiphenoate (HHDP). Addition of N-(carbobenzyloxy)-L-cysteine benzyl ester to dimethyl dehydrohexahydroxydiphenoate(s) in THF solution produces two diastereomeric S-S-cysteinyl derivatives of dimethyl hexahydroxydiphenoate.

  DOI：

  10.1021/jo971354k

文献信息

• Tannins and related compounds. CV. Monomeric and dimeric hydrolyzable tannins having a dehydrohexahydroxydiphenoyl group, supinanin, euphorscopin, euphorhelin and jolkianin, from euphorbia species.
  作者：Seung-Ho LEE、Takashi TANAKA、Gen-ichiro NONAKA、Itsuo NISHIOKA

  DOI：10.1248/cpb.39.630

  日期：——

  A chemical investigation of tannins in three Euphorbia species (E. helioscopia, E. jolkini and E. supina) has led to the isolation and characterization of four new hydrolyzable tannins, named supinanin (15), euphorscopin (16), euphorhelin (17) and jolkianin (18), together with fourteen known compounds (1-14). On the basis of chemical and spectroscopic evidence, the structures of supinanin and euphorscopin were established as 1, 3, 6-tri-O-galloyl-2, 4-(S)-dehydrohexahydroxydiphenoyl-β-D-glucose (15) and 1, 3-(S)-dehydrohexahydroxydiphenoyl-2-O-galloyl-4, 6-(S)-hexahydroxydiphenoyl-β-D-glucose (16), respectively. Euphorhelin and jolkianin were characterized as dimeric hydrolyzable tannins (17 and 18, respectively), in which two glucopyranose units are linked via valoneoyl and dehydrodigalloyl groups, respectively, and each molecule possesses a dehydrohexahydroxydiphenoyl group.

  对三种大戟属植物（E. helioscopia, E. jolkini 和 E. supina）中的单宁进行的化学研究导致了四种新可水解单宁的分离和表征，分别命名为supinanin (15)、euphorscopin (16)、euphorhelin (17) 和 jolkianin (18)，以及十四种已知化合物 (1-14)。根据化学和光谱学证据，supinanin 和 euphorscopin 的结构被确立为1, 3, 6-三-O-鞣酸基-2, 4-(S)-脱氢六羟基二苯酰-β-D-葡萄糖 (15) 和1, 3-(S)-脱氢六羟基二苯酰-2-O-鞣酸基-4, 6-(S)-六羟基二苯酰-β-D-葡萄糖 (16)。euphorhelin 和 jolkianin 被特征化为二聚体可水解单宁 (17 和 18)，其中两个葡萄糖单位分别通过瓦碧酸和脱氢二鞣酸基连接，并且每个分子都具有一个脱氢六羟基二苯酰基。
• Tannins and related compounds. XCVI. Structures of macaranins and macarinins, new hydrolyzable tannins possessing macaranoyl and tergalloyl ester groups, from the leaves of Macaranga sinensis (Baill.) Muell.-Arg.
  作者：Jer-Huei LIN、Makoto ISHIMATSU、Takashi TANAKA、Gen-ichiro NONAKA、Itsuo NISHIOKA

  DOI：10.1248/cpb.38.1844

  日期：——

  Together with eleven known compounds (1-11), seven new tannins, 3-desgalloylterchebin (12), macaranins A, B and C, and macarinins A, B and C, have been isolated from the leaves of Macaranga sinensis (BAILL.) MUELL.-ARG. (Euphorbiaceae). Macaranins A (14), B (13) and C (17) have been determined on the basis of chemical and spectroscopic evidence to be hydrolyzable tannins possessing a novel acyl group (macaranoly group) at the 3, 6-positions of the 1C4 (or skew boat) β-D-glucopyranose ring, while macarinins A (18), B (15) and (16) were characterized as those having a tergalloyl group at the same positions.

  与已知的十一种化合物（1-11）一起，从Macaranga sinensis (BAILL.) MUELL.-ARG.（大戟科）的叶子中分离出了七种新单宁，分别为3-desgalloylterchebin（12）、macaranins A、B和C。根据化学和光谱证据，确定macaranins A（14）、B（13）和C（17）为可水解的单宁，具有在1C4（或倾斜船型）β-D-葡萄糖环的3、6位上的新型酰基（macaranoly基团），而macarinins A（18）、B（15）和C（16）被鉴定为在相同位置具有tergalloyl基团的化合物。
• Tannins and related compounds. XCV. Isolation and characterization of helioscopinins and helioscopins, four new hydrolyzable tannins from Euphorbia helioscopia L. (1).
  作者：Seung-Ho LEE、Takashi TANAKA、Gen-ichiro NONAKA、Itsuo NISHIOKA

  DOI：10.1248/cpb.38.1518

  日期：——

  A chemical examination of polyphenols in Euphorbia helioscopia L. (Euphorbiaceae) has led to the isolation of four new hydrozable tannins named helioscopinins A (10) and B (9), and helioscopins A (11) and B (12), together with eight known tannins (1-8). On the basis of chemical and spectroscopic evidence, the structures of compounds 9-12 were established as 1, 6-(S)-hexahydroxydiphenoyl-3-O-galloyl-β-D-glucose, 1, 6-(S)-hexahydroxydiphenoyl-2, 4-(S)-dehydrohexahydroxydiphenoyl-3-O-galloyl-β-D-glucose, 1, 6-(S)-hexahydroxydiphenoyl-2, 4-(R)-elaeocarpusionoyl-3-O-galloyl-β-D-glucose and 1, 3, 6-tri-O-galloyl-2, 4-(R)-elaeocarpusinoyl-β-D-glucose, respectively.

  对大戟科植物日照大戟（Euphorbia helioscopia L.）中的多酚进行了化学分析，分离出四种新的水解鞣酸，分别命名为helioscopinins A (10) 和 B (9)，以及helioscopins A (11) 和 B (12)，同时还发现了八种已知的鞣酸（1-8）。根据化学和光谱证据，化合物9-12的结构被确认分别为：1, 6-(S)-六羟基二苯酰基-3-O-鞣酸基-β-D-葡萄糖，1, 6-(S)-六羟基二苯酰基-2, 4-(S)-脱氢六羟基二苯酰基-3-O-鞣酸基-β-D-葡萄糖，1, 6-(S)-六羟基二苯酰基-2, 4-(R)-油青果酸-3-O-鞣酸基-β-D-葡萄糖和1, 3, 6-三-O-鞣酸基-2, 4-(R)-油青果酸-β-D-葡萄糖。
• Tannins and related polyphenols of euphorbiaceous plants. V. Euphorbin C, an equilibrated dimeric dehydroellagitannin having a new tetrameric galloyl group.
  作者：Takashi YOSHIDA、Osamu NAMBA、Ling CHEN、Takuo OKUDA

  DOI：10.1248/cpb.38.86

  日期：——

  Euphorbin C (5), a member of a new class of dimeric hydrolyzable tannins, has been isolated form Euphorbia hirta L. In its molecule, a monomeric hydrolyzable tannin unit having a 1C4 glucopyranose core which is esterified with an equilibrated dehydrohexahydroxydiphenoyl group, and another monomer unit having a 4C1 glucose core are bonded through ester linkages of a euphorbinoyl group, which is a new galloyl tetramer.

  Euphorbin C (5)是新型二聚性可水解单宁的一员，已从大戟属植物Euphorbia hirta L.中分离出来。在其分子中，具有1C4葡萄糖吡喃糖核心的单体可水解单宁单元与一种平衡的去氢六羟基二苯酰基团酯化，另一个单体单元则具有4C1葡萄糖核心，这两者通过一种新的Galloyl四聚体——Euphorbinoyl基团的酯键连接在一起。
• Constituents of Geranium thunbergii Sieb. et Zucc. IV. Ellagitannins. 2. Structure of geraniin.
  作者：TAKUO OKUDA、TAKASHI YOSHIDA、HIDEKAZU NAYESHIRO

  DOI：10.1248/cpb.25.1862

  日期：——

  The main tannin of Geranium thunbergii has been isolated as yellow crystals, and named geraniin. Geraniin gave upon hydrolysis in boiling water, gallic acid, hexahydroxydiphenic acid, ellagic acid, and corilagin, and is shown by the proton nuclear magnetic resonance spectra to be a corilagin derivative esterified at O-2 and O-4 of D-glucopyranose in the molecule. Upon condensation with o-phenylenediamine, geraniin yielded a phenazine derivative, named phenazine A (X), which was transformed into phenazine B (XI) upon prolonged reaction. These two phenazine derivatives gave phenazine C (XII) by further prolonged reaction, or by hydrolysis of X or XI in boiling water. Corilagin was also isolated from the hydrolysis products mixture. The structure of phenazine C was proved by identification of its hydrolyzed product XV with synthetic specimen which was prepared via hydrogenolysis of dimethyl dimethoxytetrabenzyloxydiphenoate. These data along with the PMR spectra show that the structure of geraniin to be I. The carbon nuclear magnetic resonance spectra of geraniin indicate partial hydration to form geminal diol at the cyclohexenetrione moiety.

  天竺葵的主要单宁已被分离为黄色晶体，并命名为天竺葵苷。香叶苷在沸水中水解得到没食子酸、六羟基联苯酸、鞣花酸和柯里拉金，质子核磁共振谱表明是在D-吡喃葡萄糖的O-2和O-4处酯化的柯里拉京衍生物。分子。与邻苯二胺缩合后，香叶素生成吩嗪衍生物，命名为吩嗪 A (X)，经过长时间反应，该衍生物转化为吩嗪 B (XI)。这两种吩嗪衍生物通过进一步延长反应，或者通过X或XI在沸水中的水解得到吩嗪C(XII)。还从水解产物混合物中分离出柯里拉金。通过二甲氧基四苄氧基联苯甲酸二甲酯氢解制备的合成样品鉴定吩嗪C的水解产物XV，证明了吩嗪C的结构。这些数据与PMR谱一起表明香叶苷的结构为I。香叶苷的碳核磁共振谱表明在环己烯三酮部分部分水合形成偕二醇。