4-methoxy-3-(2,3,4-trimethoxy-6-methoxycarbonyl-phenyl)-phenazine-2-carboxylic acid methyl ester | 18473-68-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-methoxy-3-(2,3,4-trimethoxy-6-methoxycarbonyl-phenyl)-phenazine-2-carboxylic acid methyl ester
• 英文别名: methyl 4-methoxy-3-(2,3,4-trimethoxy-6-methoxycarbonylphenyl)phenazine-2-carboxylate
• CAS: 18473-68-2；18587-96-7；99493-11-5
• 化学式: C₂₆H₂₄N₂O₈
• 分子量: 492.485
• InChiKey: KSVHVKISJJXWGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4-methoxy-3-(2,3,4-trimethoxy-6-methoxycarbonyl-phenyl)-phenazine-2-carboxylic acid methyl ester 在 sodium methoxide-d3 作用下， 生成
  参考文献：
  名称：

  Okuda, Takuo; Yoshida, Takashi; Hatano, Tsutomu, Journal of the Chemical Society. Perkin transactions I, 1982, p. 9 - 14

  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 、 溶剂黄146 、 乙腈 为溶剂， 反应 30.0h， 生成 4-methoxy-3-(2,3,4-trimethoxy-6-methoxycarbonyl-phenyl)-phenazine-2-carboxylic acid methyl ester
  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 of Euphorbiaceous Plants. X. Antidesmin A, a New Dimeric Hydrolyzable Tannin from Antidesma pentandrum var. barbatum.
  作者：Takashi YOSHIDA、Osamu NAMBA、Che-Feng LU、Ling-Ling YANG、Kun-Ying YEN、Takuo OKUDA

  DOI：10.1248/cpb.40.338

  日期：——

  A new hydrolyzable tannin, antidesmes A (4), was isolated along with carpinusin (1) and geraniin (2) from dried leaves of Antidesma pentandrum MERR, var. barbatum MERR., and its dimeric structure, composed of devidiin (3) and geraniin (2), has been elucidated by spectral and chemical methods.

  一种新的可水解单宁，抗单宁A（4），与卡宾酚（1）和香叶酸（2）一起从Antidesma pentandrum MERR，var. barbatum MERR.的干叶中分离出来，其二聚体结构由去乙烯二酚（3）和香叶酸（2）组成，已经通过光谱和化学方法确定。
• 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。
• Okuda, Takuo; Hatano, Tsutomu; Yasui, Tsutomu, Heterocycles, 1981, vol. 16, # 8, p. 1321 - 1324
  作者：Okuda, Takuo、Hatano, Tsutomu、Yasui, Tsutomu

  DOI：——

  日期：——

表征谱图