3,4,5-trimethoxy-2-(3,7,8-trimethoxy-5,10-dioxo-5,10-dihydro-chromeno[5,4,3-cde]chromen-2-yloxy)-benzoic acid methyl ester | 53547-85-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: 3,4,5-trimethoxy-2-(3,7,8-trimethoxy-5,10-dioxo-5,10-dihydro-chromeno[5,4,3-cde]chromen-2-yloxy)-benzoic acid methyl ester
• 英文别名: 3,4,5-Trimethoxy-2-(3,7,8-trimethoxy-5,10-dioxo-5,10-dihydro-chromeno[5,4,3-cde]chromen-2-yloxy)-benzoesaeure-methylester；methyl 3,4,5-trimethoxy-2-[(7,13,14-trimethoxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),4,6,8(16),11,13-hexaen-6-yl)oxy]benzoate
• CAS: 53547-85-6
• 化学式: C₂₈H₂₄O₁₃
• 分子量: 568.491
• InChiKey: LCAXRIIRSCPLQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.12
• 重原子数：
  41.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  151.33
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  3,4,5-trimethoxy-2-(3,7,8-trimethoxy-5,10-dioxo-5,10-dihydro-chromeno[5,4,3-cde]chromen-2-yloxy)-benzoic acid methyl ester 在 sodium hydroxide 作用下， 生成 rac. Octa-O-methyl-valoneasaeure
  参考文献：
  名称：

  Schmidt; Komarek, Justus Liebigs Annalen der Chemie, 1955, vol. 591, p. 156,170

  摘要：

  DOI：
• 作为产物：
  描述：

  生成 3,4,5-trimethoxy-2-(3,7,8-trimethoxy-5,10-dioxo-5,10-dihydro-chromeno[5,4,3-cde]chromen-2-yloxy)-benzoic acid methyl ester
  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：

文献信息

• Tannins and Related Polyphenols of Melastomataceous Plants. III. Nobotanins G, H and I, Dimeric Hydrolyzable Tannins from Heterocentron roseum.
  作者：Takashi YOSHIDA、Kumiko HABA、Fumihisa NAKATA、Yoshiaki OKANO、Tetsuro SHINGU、Takuo OKUDA

  DOI：10.1248/cpb.40.66

  日期：——

  Three new hydrolyzable tannin dimers, nobotanins G (6), H (12) and I (13), have been isolated from the leaves of Heterocentron roseum (Melastomataceae), and their structures were elucidated on the basis of chemical degradations and nuclear magnetic resonance spectral analyses. Nobotanin I (13) is a novel dimer possessing a depsidone-forming valoneoyl group in the molecule. Five known tannins, casuarictin (1), strictinin (2), geraniin (3), and nobotanins B (4) and F (5), were also isolated.

  三种新的水解单宁二聚体，诺博塔宁G (6)、H (12) 和I (13)，已从玫瑰异菊（Melastomataceae）叶中分离出来，其结构通过化学降解和核磁共振光谱分析得以阐明。诺博塔宁I (13) 是一种新型二聚体，分子中具有形成环状酮的香豆酸基团。此外，还分离出了五种已知的单宁，包括卡苏里克丁 (1)、严格单宁 (2)、香草松 (3)、以及诺博塔宁B (4) 和F (5)。
• Oenotheins D, F and G, hydrolysable tannin dimers from Oenothera laciniata
  作者：Takashi Yoshida、Tong Chou、Tetsuro Shingu、Takuo Okuda

  DOI：10.1016/0031-9422(95)00267-b

  日期：1995.9

  Three new dimeric hydrolysable tannins, oenotheins D, F and G, together with known tannins including the macrocyclic oligomers, oenotheins A and B, have been isolated from roots and stems of Oenothera laciniata. Their structures were elucidated on the basis of chemical and spectral evidence. Oenotheins D and F were macrocyclic dimers isomeric with oenothein B in relation to the orientation of the valoneoyl

  从月见草的根和茎中分离出三种新的二聚体可水解单宁，月见草苷 D、F 和 G，以及已知的单宁，包括大环低聚物，月见草苷 A 和 B。根据化学和光谱证据阐明了它们的结构。Oenotheins D 和 F 是大环二聚体，与 Oenothein B 的异构体与连接单体的丙戊酰基团的方向有关。
• 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。
• Tannins and related compounds. CVI. Preparation of aminoalditol derivatives of hydrolyzable tannins having .ALPHA.-and .BETA.-glucopyranose cores, and its application to the structure elucidation of new tannins, reginins A and B and flosin A, isolated from Lagerstroemia flos-reginae Retz.
  作者：Ya-Ming XU、Takashi SAKAI、Takashi TANAKA、Gen-ichiro NONAKA、Itsuo NISHIOKA

  DOI：10.1248/cpb.39.639

  日期：——

  To avoid tautomerism in the hydrolyzable tannins which lack an acyl group at the glucose C-1 position, a new method for the protection fo the C-1 atom has been developed. That is reaction of the tannins with p-anisidine in the presence of acetic acid, followed by sodium cyanoborohydride reduction, afforded, without notable hydrolysis of ester bonds, the aminoalditol derivatives (1a-7a) in 50-80% yields. The proton and carbon-13 nuclear magnetic resonance (1H-and 13C-NMR) spectra of these derivatives exhibited much simpler signal patterns typical of an open-chain form of glucose, and almost all the singals could be assigned.Application of this method to the structure elucidation of the new tannins, flosin A (22) and reginins A (23) and B (24), isolated from the leaves of Lagerstroemia flos-reginae RETZ. (Lythraceae), established their structures including the orientation of the 4, 6-positioned valoneoyl group. In addition, the structure of a new hydrolyzable tannin, lagerstroemin (21), which was concomitantly isolated from the above species, was elucidated.

  为了避免在葡萄糖C-1位缺乏酰基的可水解单宁中的互变异构，已经开发了一种新的C-1原子保护方法。即在乙酸存在下，单宁与对氨基苯甲醚发生反应，然后进行氰硼氢化钠还原，在不显著水解酯键的情况下，以50-80%的产率得到氨基醛糖衍生物（1a-7a）。这些衍生物的质子和碳-13核磁共振（1H-和13C-NMR）光谱显示出更简单的信号模式，这是葡萄糖开链形式的典型特征，并且几乎所有信号都可以被分配。将这种方法应用于从紫薇（Lagerstroemia flos-reginae RETZ）的叶子中分离出的新单宁、紫薇素A（22）和紫薇素A（23）和B（24）的结构阐明，确定了它们的结构，包括4、6位戊烯酰基的方向。此外，还阐明了从上述物种中同时分离出的新可水解单宁紫薇素（21）的结构。
• YOSHIDA, TAKASHI;CHOU, TONG;NITTA, AYA;MIYAMOTO, KEN-ICHI;KOSHIURA, RYOZO+, CHEM. AND PHARM. BULL., 38,(1990) N, C. 1211-1217
  作者：YOSHIDA, TAKASHI、CHOU, TONG、NITTA, AYA、MIYAMOTO, KEN-ICHI、KOSHIURA, RYOZO+

  DOI：——

  日期：——