trimethylocta-O-methylvalonate | 118964-21-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: trimethylocta-O-methylvalonate
• 英文别名: trimethyl octa-O-methylvaloneate；(+/-)-5,6,4',5',6'-pentamethoxy-4-(2,3,4-trimethoxy-6-methoxycarbonyl-phenoxy)-diphenic acid dimethyl ester；(+/-)-5,6,4',5',6'-Pentamethoxy-4-(2,3,4-trimethoxy-6-methoxycarbonyl-phenoxy)-diphensaeure-dimethylester；Methyl 2-[2,3-dimethoxy-6-methoxycarbonyl-4-(2,3,4-trimethoxy-6-methoxycarbonylphenoxy)phenyl]-3,4,5-trimethoxybenzoate
• CAS: 118964-21-9
• 化学式: C₃₂H₃₆O₁₅
• 分子量: 660.629
• InChiKey: UZMUDBUEZHFABW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  47
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  162
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  3,4-二甲氧基-5-羟基苯甲酸甲酯 在 溴 、 铜 作用下， 反应 10.08h， 生成 trimethylocta-O-methylvalonate
  参考文献：
  名称：

  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.

  摘要：

  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。

  DOI：

  10.1248/cpb.38.1844

文献信息

• Hirsunin, an ellagitannin with a diarylheptanoid moiety, from Alnus hirsuta var. Microphylla
  作者：Lee Min-Won、Takashi Tanaka、Gen-Ichiro Nonaka、Itsuo Nishioka

  DOI：10.1016/0031-9422(92)80049-k

  日期：1992.3

  and the structure which consists of diarylheptanoid glycoside (oregonin) and ellagitannin (praecoxin A) moieties connected through an ester linkage has been elucidated. Furthermore, the occurrence of the seven known hydrolysable tannins, pedunculagin, praecoxin A, 1,2,6- and 1,4,6-tri- O -galloyl-β- d -glucoses, 1-desgalloyleugeniin, 1-desgalloylrugosin F, and rugosin F, along with oregonin and gentisic

  摘要 从桤木的叶子中分离到了一种新的鞣花单宁，hirsunin。小叶和由通过酯键连接的二芳基庚烷苷（oregonin）和鞣花单宁（praecoxin A）部分组成的结构已被阐明。此外，七种已知的可水解单宁、花梗素、普瑞考辛 A、1,2,6- 和 1,4,6-三-O-没食子酰-β-d-葡萄糖、1-去没食子酰白菜素、1-去没食子酰白菜素 F、和 rugosin F 以及俄勒冈素和龙胆酸 5-O-β-d-(6'-O-没食子酰基)-吡喃葡萄糖苷也已得到证实。
• 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. CXXIV. Five New Ellagitannins, Platycaryanins A, B, C, and D, and Platycariin, and a New Complex Tannin, Strobilanin, from the Fruits and Bark of Platycarya strobilacea SIEB et ZUCC., and Biomimetic Synthesis of C-Glycosidic Ellagitannins from Glucopyranose-Based Ellagitannins.
  作者：Takashi TANAKA、Shinji KIRIHARA、Gen-ichiro NONAKA、Itsuo NISHIOKA

  DOI：10.1248/cpb.41.1708

  日期：——

  Five new ellagitannins, platycaryanins A (27), B (26), C (30), and D (25), and platycariin (31), and a new complex tannin, strobilanin (32), have been isolated from the fruits and bark of Platycarya strobilacea SIEB. et ZUCC. (Juglandaceae), together with twenty-six known compounds. On the basis of spectroscopic and chemical evidence, platycaryanins A, B and C, and platycariin have been characterized as the ellagitannins having a tergalloyl ester group, while platycaryanin D was found to be an unusual ellagitannin possessing (R)-hexahydroxydiphenoyl esters at the glucopyranose 2, 3- and 4, 6-positions. During these chemical studies, re-examination of the similar ellagitannins, alnusnins A and B, which were previously reported from Alnus sieboldiana, led us to revise their structures to 29 and 28, respectively, in which the tergalloyl group forms a lactone ring. Furthermore, biomimetic conversion of ellagitannins having a glucopyranose core into C-glycosidic ellagitannins was successfully achieved for the first time, and the reaction was applied to the structure elucidation of platycariin (31).

  从Platycarya strobilacea SIEB. et ZUCC.（胡桃科）的果实和树皮中分离出了五种新的鞣花酸类化合物，分别是platycaryanins A（27）、B（26）、C（30）和D（25），以及platycariin（31），同时还分离出了二十六种已知化合物。根据光谱学和化学证据，platycaryanins A、B和C以及platycariin被鉴定为具有军团酸酯基团的鞣花酸类化合物，而platycaryanin D则被发现是一种不寻常的鞣花酸，具有在葡萄糖吡喃糖2、3位和4、6位的(R)-六羟基二苯酸酯。在这些化学研究过程中，对以前从Alnus sieboldiana分离出的相似鞣花酸alnusnins A和B进行了重新审查，导致我们修正了它们的结构，分别为29和28，其中军团酸基团形成了内酯环。此外，首次成功实现了将具有葡萄糖吡喃核的鞣花酸转化为C-糖苷鞣花酸的生物仿生转化，该反应被应用于platycariin（31）的结构阐明。
• 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 of cornaceous plants. I. Cornusiins A, B and C, dimeric monomeric and trimeric hydrolyzable tannins from Cornus officinalis, and orientation of valoneoyl group in related tannins.
  作者：Tsutomu HATANO、Noboru OGAWA、Reiko KIRA、Taeko YASUHARA、Takuo OKUDA

  DOI：10.1248/cpb.37.2083

  日期：——

  Cornusiin A (1), cornusiin B (2) and cornusiin C (3), new dimeric monomeric and trimeric hydrolyzable tannins, were isolated from the fruits of cornus officinalis (Cornaceae). Their structures, including the orientation of the valoneoyl group in 1 and 3, were established on the basis of chemical and spectroscopic data. 2, 3-Di-O-galloyl-D-glucose (7), 1, 2, 3-tri-O-galloyl-β-D-glucose, 1, 2, 6-tri-O-galloyl-β-D-glucose, 1, 2, 3, 6-tetra-O-galloyl-β-D-glucose, gemin D (5), isoterchebin, tellimagrandin I (6) and tellimagrandin II were also isolated from the fruits. The orientation of the valoneoyl group in camptothin A (14) and that in camptothin B (15), which had been isolated from Camptotheca acuminata (Nyssaceae), were also determined based on that in 1.

  从 Cornus officinalis（山茱萸科）的果实中分离出了新型二聚单体和三聚水解鞣花酸，分别为 Cornusiin A (1)、Cornusiin B (2) 和 Cornusiin C (3)。它们的结构，包括 1 和 3 中 valoneoyl 基团的取向，是基于化学和光谱数据确定的。此外，还从果实中分离出了 2, 3-二-O-没食子酸-D-葡萄糖 (7)、1, 2, 3-三-O-没食子酸-β-D-葡萄糖、1, 2, 6-三-O-没食子酸-β-D-葡萄糖、1, 2, 3, 6-四-O-没食子酸-β-D-葡萄糖、gemin D (5)、isoterchebin、tellimagrandin I (6) 和 tellimagrandin II。Camptotheca acuminata（黄樟科）中分离出的 camptothin A (14) 和 camptothin B (15) 中 valoneoyl 基团的取向也是基于 1 的取向确定的。