6,7-dihydroxy-1,1-dimethylisochromane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6,7-dihydroxy-1,1-dimethylisochromane
• 英文别名: 1,1-dimethyl-6,7-dihydroxyisochroman；1,1-dimethylisochroman-6,7-diol；6,7-Dihydroxy-1,1-dimethylisochroman；1,1-dimethyl-3,4-dihydroisochromene-6,7-diol
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: OJBLPQSINZETOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  橄榄苦甙 在 Amberlyst 15 、 4 A molecular sieve 、 camphor-10-sulfonic acid 、 对甲苯磺酸 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 14.0h， 生成 6,7-dihydroxy-1,1-dimethylisochromane
  参考文献：
  名称：

  通过全合成和天然糖苷橄榄苦苷的高产率制备羟基酪醇的稳定前体。

  摘要：

  抗氧化剂羟基酪醇前所未有的丙酮化物已通过两步高产率程序合成，发现既可通过色谱纯化，又可在较宽的pH范围内稳定。该保护作用稳定了羟基酪醇免于氧化，从而可以长期保存。可以在非水条件下定量去除保护层，以提供适合用作食品和化妆品制剂中添加剂的纯羟基酪醇。将相同的方法扩展至天然且容易获得的苷橄榄苦苷，然后将所得的丙酮化物复杂混合物皂化，可以高收率回收羟基酪醇丙酮化物。这构成了获得抗氧化剂羟基酪醇的新的有趣方法。

  DOI：

  10.1021/jf063353b

文献信息

• One-Pot Synthesis of 6-Hydroxyisochromans: The Example of Demethyl-oxa-coclaurine
  作者：Marcella Guiso、Armandodoriano Bianco、Carolina Marra、Claudia Cavarischia

  DOI：10.1002/ejoc.200300182

  日期：2003.9

  The successful one step synthesis did not require protecting groups and provided high yields. The obtainment of 1-(4′-hydroxybenzyl)-6,7-dihydroxyisochroman (1) indicates that this protocol can be used to synthesize oxygenated analogues of benzyl-tetrahydroisoquinoline alkaloids, such as demethyl-coclaurine (2). This methodology could provide a general procedure for the synthesis of hydroxyisochromans

  使用我们最近描述的修改过的 oxa-Pictet Spengler 反应，我们合成了 6-羟基-异色满及其 7-羟基衍生物。成功的一步合成不需要保护基团并提供了高产率。1-(4'-hydroxybenzyl)-6,7-dihydroxyisochroman (1) 的获得表明该协议可用于合成苄基-四氢异喹啉生物碱的含氧类似物，如 demethyl-coclaurine (2)。这种方法可以提供合成羟基异色满的通用程序。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Synthesis and antioxidant evaluation of isochroman-derivatives of hydroxytyrosol: Structure–activity relationship
  作者：Raquel Mateos、Andrés Madrona、Gema Pereira-Caro、Vanessa Domínguez、Rosa M.a Cert、Juan Parrado、Beatriz Sarriá、Laura Bravo、José Luis Espartero

  DOI：10.1016/j.foodchem.2014.10.036

  日期：2015.4

  Isochroman-derivatives of the natural olive oil phenol hydroxytyrosol (HT) have been synthesised via Oxa-Pictet-Spengler reaction in high yields. Lipophilicity and antioxidant activity were determined to establish the structure-activity relationship of isochromans compared to HT, BHT and alpha-tocopherol. Antioxidant capacity was tested in two different media: bulk oils, using the Rancimat test, and brain homogenates, by measuring malondialdehyde (MDA) levels as a lipoperoxidation biomarker. In addition, other antioxidant assays (FRAP, ABTS and ORAC) were carried out. Rancimat and MDA results show that antioxidant activity was related with lipophilicity, directly in brain homogenates and inversely in the oils, in agreement with the polar paradox. Free o-diphenolic groups positively determined the activity in the oils, whereas reducing and radical-scavenging activities were related to the number of free hydroxyl moieties. BHT and a-tocopherol showed lower antioxidant activity than isochromans and HT. We conclude that HT-isochromans present significant potential as bioactive compounds. (C) 2014 Elsevier Ltd. All rights reserved.
• Isochromans from 2-(3′,4′-dihydroxy)phenylethanol
  作者：Marcella Guiso、Carolina Marra、Claudia Cavarischia

  DOI：10.1016/s0040-4039(01)01307-7

  日期：2001.9

  A facile method to obtain an isochromanic structure was achieved by the oxa-Pictet-Spengler reaction using 2-(3',4'-dihydroxy)phenylethanol as starting material. The reaction was performed in very mild conditions on a series of carbonylic compounds. Yields were always satisfactory. (C) 2001 Elsevier Science Ltd. All rights reserved.
• High-Yielding Preparation of a Stable Precursor of Hydroxytyrosol by Total Synthesis and from the Natural Glycoside Oleuropein
  作者：Augusto Gambacorta、Daniela Tofani、Roberta Bernini、Antonella Migliorini

  DOI：10.1021/jf063353b

  日期：2007.5.1

  by a two-step high-yielding procedure and found to be both purifiable by chromatography and stable over a wide pH range. The protection stabilizes hydroxytyrosol against oxidation, thereby allowing long-term storage. The protection can quantitatively be removed, under nonaqueous conditions, to afford pure hydroxytyrosol suitable for use as an additive in food and cosmetic preparations. Extension of

  抗氧化剂羟基酪醇前所未有的丙酮化物已通过两步高产率程序合成，发现既可通过色谱纯化，又可在较宽的pH范围内稳定。该保护作用稳定了羟基酪醇免于氧化，从而可以长期保存。可以在非水条件下定量去除保护层，以提供适合用作食品和化妆品制剂中添加剂的纯羟基酪醇。将相同的方法扩展至天然且容易获得的苷橄榄苦苷，然后将所得的丙酮化物复杂混合物皂化，可以高收率回收羟基酪醇丙酮化物。这构成了获得抗氧化剂羟基酪醇的新的有趣方法。