(E)-1-(3-acetoxy-5-O-2,3,4,6-tetraacetyl-β-D-glucopyranosidophenyl)-2-(4'-acetoxyphenyl)ethene | 62502-04-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-1-(3-acetoxy-5-O-2,3,4,6-tetraacetyl-β-D-glucopyranosidophenyl)-2-(4'-acetoxyphenyl)ethene
• 英文别名: piceid peracetate；4',5-diacetoxy-3-(tetra-O-acetyl-β-D-glucopyranosyloxy)stilbene；(5,4'-diacetoxy-trans-stilben-3-yl)-(tetra-O-acetyl-β-D-glucopyranoside)；(5,4'-Diacetoxy-trans-stilben-3-yl)-(tetra-O-acetyl-β-D-glucopyranosid)；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[3-acetyloxy-5-[(E)-2-(4-acetyloxyphenyl)ethenyl]phenoxy]oxan-2-yl]methyl acetate
• CAS: 62502-04-9
• 化学式: C₃₂H₃₄O₁₄
• 分子量: 642.614
• InChiKey: SNYBSHYQXLLNSS-DXTZNUPESA-N

物化性质

• 熔点：
  153-154 °C
• 沸点：
  710.9±60.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  46
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  176
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  (E)-1-(3-acetoxy-5-O-2,3,4,6-tetraacetyl-β-D-glucopyranosidophenyl)-2-(4'-acetoxyphenyl)ethene 在 Burkholderia cepacia lipase immobilized on diatomaceous earth 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 生成 5-acetoxy-3-(tetra-O-acetyl-β-D-glucopyranosyloxy)-4'-hydroxystilbene
  参考文献：
  名称：

  Short-step syntheses of naturally occurring polyoxygenated aromatics based on site-selective transformation

  摘要：

  摘要：Wogonin和astringin是从廉价的芹菜素和白藜芦醇中经过简短步骤合成的。这些合成的关键特点是位点选择性转化。从起始材料中，目标分子分别以27%和62%的产率获得。

  DOI：

  10.1080/09168451.2017.1303362
• 作为产物：
  描述：

  2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 吡啶 、 4-二甲氨基吡啶 、 palladium diacetate 、 三正丁胺 、 苄基三乙基氯化铵 、 silver carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 10.0h， 生成 (E)-1-(3-acetoxy-5-O-2,3,4,6-tetraacetyl-β-D-glucopyranosidophenyl)-2-(4'-acetoxyphenyl)ethene
  参考文献：
  名称：

  A Novel, Convenient Synthesis of the 3‐O‐β‐D‐ and 4′‐O‐β‐D‐Glucopyranosides of trans‐Resveratrol

  摘要：

  trans-Resveratrol-3-O-beta-D-glueupyranoside (trans-piceid, 2) and trans-resveratrol-4'-O-beta-D-glucupyranoside (trans-resveratroloside 3) are the naturally occurring O-glucoside conjugates of the polyphenolic stilbenoid trans-resveratrol 1. Recently, attention has been drawn towards the interesting biological properties of the glucoside conjugates 2 and 3 as well as those of the aglycone 1. The fact that only limited quantities can be obtained by extraction from natural sources has prompted the development of novel syntheses of 2 and 3, based on a convergent Heck-coupling strategy, which now conveniently allows for the preparation of multimilligram to gram quantities of each.

  DOI：

  10.1081/scc-120030744

文献信息

• A Bifunctional Iron Nanocomposite Catalyst for Efficient Oxidation of Alkenes to Ketones and 1,2-Diketones
  作者：Tao Song、Zhiming Ma、Peng Ren、Youzhu Yuan、Jianliang Xiao、Yong Yang

  DOI：10.1021/acscatal.9b05197

  日期：2020.4.17

  sites of Fe–Nx and Fe phosphate, as oxidation and Lewis acid sites, were simultaneously integrated into a hierarchical N,P-dual doped porous carbon. As a bifunctional catalyst, it exhibited high efficiency for direct oxidative cleavage of alkenes into ketones or their oxidation into 1,2-diketones with a broad substrate scope and high functional group tolerance using TBHP as the oxidant in water under

  我们在此报告了一种双功能铁纳米复合催化剂的制备，其中两个Fe–N x催化活性位点磷酸铁和铁的氧化位和路易斯酸位同时被整合到一个分层的N，P-双掺杂多孔碳中。作为一种双功能催化剂，它具有良好的催化作用，可在较温和的反应条件下使用TBHP作为氧化剂，将烯烃直接氧化裂解为酮或将其氧化为1,2-二酮，具有广泛的底物范围，并具有较高的官能团耐受性。此外，可以很容易地将其回收以进行后续回收，而不会造成明显的活性损失。机理研究表明，烯烃的直接氧化是通过形成环氧化物作为中间体，然后进行酸催化的Meinwald重排而产生的，该酮的碳原子短了一个或亲核开环，从而以级联方式生成1,2-二酮。
• Synthesis of acacetin and resveratrol 3,5-di-O-β-glucopyranoside using lipase-catalyzed regioselective deacetylation of polyphenol glycoside peracetates as the key step
  作者：Shun Hanamura、Kengo Hanaya、Mitsuru Shoji、Takeshi Sugai

  DOI：10.1016/j.molcatb.2016.03.001

  日期：2016.6

  Acacetin and re sveratrol 3,5-di-O-beta-glucopyranoside were synthesized from naturally abundant naringin and piceid in 65% and 62% overall yield, respectively. The key steps were the regioselective deacetylation of the peracetates of the glycosylated forms with Candida antarctica lipase B (Novozym 435) and Burkholderia cepacia lipase (Amano PS-IM). Deacetylation occurred exclusively at the least hindered position of the aromatic moieties and all acetyl groups in the sugar side chain remained intact. This excellent selectivity enabled regiospecific transformation of the liberated phenolic hydroxy groups, resulting in efficient synthesis of the target molecules. (C) 2016 Elsevier B.V. All rights reserved.
• Hathway; Seakins, Biochemical Journal, 1959, vol. 72, p. 369,370
  作者：Hathway、Seakins

  DOI：——

  日期：——
• Synthetic Communications 2004, 34, 1565-1575
  作者：

  DOI：——

  日期：——