dihydroxanthyletin | 21074-63-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: dihydroxanthyletin
• 英文别名: 2,2-dimethyl-3,4-dihydropyrano[3,2-g]chromen-8-one
• CAS: 21074-63-5
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: OHVLVQZSSLHFMS-UHFFFAOYSA-N

物化性质

• 熔点：
  102-104 °C
• 沸点：
  378.9±42.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  dihydroxanthyletin 在 ammonium cerium (IV) nitrate 、 溶剂黄146 、 potassium hydroxide 作用下， 以 乙醚 、 水 为溶剂， 反应 0.58h， 生成 3-hydroxy-4,4-dimethoxy-2,2-dimethyl-3H-pyrano[3,2-g]chromen-8-one
  参考文献：
  名称：

  Total Synthesis of (±)-Scuteflorin A

  摘要：

  A highly efficient synthesis was developed for the first total synthesis of scuteflorin A. (c) 2010 Elsevier Science. All rights reserved.

  DOI：

  10.3987/com-10-12030
• 作为产物：
  描述：

  美洲花椒素 在 乙醇 、 钯 作用下， 生成 dihydroxanthyletin
  参考文献：
  名称：

  406.美洲花椒皮的成分。第二部分 黄thy素

  摘要：

  DOI：

  10.1039/jr9360001828

文献信息

• NEW COMPOUND FOR INHIBITING BINDING BETWEEN DX2 PROTEIN AND P14/ARF PROTEIN, AND PHARMACEUTICAL COMPOSITION FOR TREATING OR PREVENTING CANCER DISEASE CONTAINING SAME AS EFFECTIVE INGREDIENT
  申请人：PUSAN NATIONAL UNIVERSITY INDUSTRY-UNIVERSITY COOPERATION FOUNDATION

  公开号：US20170129904A1

  公开（公告）日：2017-05-11

  Disclosed is a new compound that inhibits binding between a DX2 protein and a p14/ARF protein, a pharmaceutical composition including the new compound as an effective component for treating or preventing a cancer disease, an anticancer adjuvant for improving an anticancer effect of a drug-resistant anticancer drug, and a composition including an AIMP2-DX2 protein or a fragment thereof for diagnosing lung cancer.

  披露了一种新化合物，该化合物抑制了DX2蛋白与p14/ARF蛋白之间的结合，包括该新化合物作为治疗或预防癌症疾病的有效成分的药物组合物，用于提高耐药抗癌药物的抗癌效果的抗癌辅助剂，以及包括AIMP2-DX2蛋白或其片段的组合物，用于诊断肺癌。
• Novel syntheses of dihydroxanthyletin and dihydroseselin derivatives
  作者：Michele M. Jetter、Ned D. Heindel、Jeffrey D. Laskin

  DOI：10.1002/jhet.5570270433

  日期：1990.5

  In a one-step alkylation, ring-closure 7-hydroxycoumarins are condensed in acid media with allyl and homoallyl halides or alcohols to linear 6,7-dihydro-2H,8H-benzo[1,2–6:5,4-b']dipyran-2-ones. If both carbon-6 and carbon-8 are unsubstituted in the original coumarin, cyclization to angular isomers 9,10-dihydro-2H,8H-benzo[1,2–6:3,4-b']dipyran-2-ones competes. These compounds are higher ring homologs

  在一步式烷基化中，将闭环的7-羟基香豆素在酸介质中与烯丙基和高烯丙基卤化物或醇缩合成线性6,7-二氢-2 H，8 H-苯并[1,2–6：5,4 - b” ] dipyran -2-酮。如果原始香豆素中的碳6和碳8都未被取代，则环化成角异构体9,10-dihydro-2 H，8 H-苯并[1,2-6：3,4- b' ] dipyran-2 -竞争。这些化合物是通常用于皮肤疾病的光疗中的补骨脂素和当归素的较高环同系物。
• Efficient syntheses of 6-prenylcoumarins and linear pyranocoumarins: Total synthesis of suberosin, toddaculin, O-methylapigravin (O-methylbrosiperin), O-methylbalsamiferone, dihydroxanthyletin, xanthyletin and luvangetin
  作者：Raghao S. Mali、Priya P. Joshi、Paramjeet Kaur Sandhu、Anita Manekar-Tilve

  DOI：10.1039/b109597h

  日期：2002.1.23

  Synthesis of naturally occurring 6-prenylcoumarins (1a, 2c and 3a) and their derivatives 1c, 1d, 1e, 2d and 3b–d starting from 2-prenyloxybenzaldehydes (8, 12 and 14) using tandem Claisen rearrangement and Wittig reaction is described. The coumarins 1a, 1e and 2c are converted to dihydropyranocoumarins (5a–e). The conversion of dihydroxanthyletin 5a and dihydroluvangetin 5d to the naturally occurring linear pyranocoumarins xanthyletin 6a and luvangetin 6b is also described.

  以 2-异戊氧基苯甲醛（8、12 和 14）为起点，利用串联克莱森重排和维蒂希反应合成了天然 6-异戊基香豆素（1a、2c 和 3a）及其衍生物 1c、1d、1e、2d 和 3b-d。香豆素 1a、1e 和 2c 被转化成二氢吡喃香豆素（5a-e）。此外，还介绍了将二羟基黄皮素 5a 和二氢紫罗兰素 5d 转化为天然的线型吡喃香豆素黄皮素 6a 和紫罗兰素 6b。
• A simple and efficient approach for the preparation of dihydroxanthyletin, xanthyletin, decursinol and marmesin
  作者：Rajkumar Kommera、China Raju Bhimapaka

  DOI：10.1080/00397911.2020.1797812

  日期：2020.11.1

  Abstract A simple and efficient approach has been developed for the preparation of coumarin natural products such as dihydroxanthyletin, xanthyletin, decursinol and marmesin starting from commercially available 2,4-dihydroxybenzaldehyde with very good yields. Wittig homologation and Claisen rearrangement are the protocols used to achieve these molecules. Graphical Abstract

  摘要 已经开发了一种简单有效的方法，以非常好的收率从市售的 2,4-二羟基苯甲醛制备香豆素天然产物，例如二羟基黄苷素、黄苷素、decursinol 和 marmesin。Wittig 同源性和 Claisen 重排是用于实现这些分子的协议。图形概要
• Pharmaceutical Composition Useful as Acetylcholinesterase Inhibitors
  申请人：Rao Madhusudana Janaswamy

  公开号：US20080009544A1

  公开（公告）日：2008-01-10

  A pharmaceutical composition useful as acetylcholinesterase inhibitors. The present invention relates to pharmaceutical composition comprising the naturally occurring compounds selected from (±) Marmesin, Columbianetin, Dihydroxanthyletin and substituted coumarin derivatives of 7-allyloxy coumarin, 7-benzyloxy coumarin, 7-methoxy coumarin, 7-acetyloxy coumarin, 4-methyl-7-hydroxy coumarin and 4-methyl-7-acetyloxy coumarin. The said compositions posses a high degree of acetylcholinesterase inhibitory (AChE) property.

  一种可用作乙酰胆碱酯酶抑制剂的药物组合物。本发明涉及一种药物组合物，其包括从（±）马美辛，哥伦比亚内丁，二氢黄芪素和7-烯丙氧基香豆素，7-苄氧基香豆素，7-甲氧基香豆素，7-乙酰氧基香豆素，4-甲基-7-羟基香豆素和4-甲基-7-乙酰氧基香豆素中选择的天然化合物和取代香豆素衍生物。所述组合物具有高度的乙酰胆碱酯酶抑制（AChE）特性。