7,8-dihydromethysticin | 329351-76-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 卡瓦内酯
• 英文名称: 7,8-dihydromethysticin
• 英文别名: Dihydromethysticin, (R)-；(2R)-2-[2-(1,3-benzodioxol-5-yl)ethyl]-4-methoxy-2,3-dihydropyran-6-one
• CAS: 329351-76-0
• 化学式: C₁₅H₁₆O₅
• 分子量: 276.289
• InChiKey: RSIWXFIBHXYNFM-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (1S,2S)-1-[2-(3,4-methylenedioxyphenyl)ethyl]-2-(triisopropylsilyloxy)cyclopentane 在 sodium tetrahydroborate 、 三甲基氯硅烷 、 二苯基二硒醚 、 四丁基氟化铵 、 双氧水 、 三氧化硫吡啶 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 、 三乙胺 、 间氯过氧苯甲酸 、 pyridinium chlorochromate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 aq. phosphate buffer 、 乙醇 、 二氯甲烷 、 二甲基亚砜 、 丙酮 、 甲苯 为溶剂， 反应 43.67h， 生成 7,8-dihydromethysticin
  参考文献：
  名称：

  从两种酵母还原产物合成 (S)- 和 (R)-二氢迷幻素，可以由一种外消旋化合物制备

  摘要：

  以光学活性酵母还原产物乙酸(1,2)-甲基2-羟基环己酯()为原料，通过引入3,4-亚甲二氧基苄基、Beayer-Villiger 氧化以及转化为其烯醇化物。此外，从光学活性酵母还原产物(1 ,5 )− 2-氧杂双环[3.3.0]辛烷-3-合成了具有高对映体纯度(>99%ee)的()-二氢迷幻素(()-)。一个()，采用与()-相同的合成方法。发现这两种对映体的抗真菌活性都很弱。

  DOI：

  10.1016/j.phytol.2024.02.001

文献信息

• Heterogeneous enantioselective hydrogenation of 2-pyrones over cinchona-modified palladium
  作者：Wolf-Rüdiger Huck、Tamas Mallat、Alfons Baiker

  DOI：10.1039/b108944g

  日期：2002.1.24

  Asymmetric hydrogenation of 4-alkoxy and 4-methyl derivatives of 2-pyrones to the corresponding dihydro- or tetrahydropyrones over cinchona-modified Pd/TiO2 is fast under ambient conditions and affords good yields and high ee. cis-Tetrahydropyrones are obtained with 98–99% de. The ee can be further increased by kinetic resolution.

  不对称 氢化在环境条件下，在金鸡纳改性的Pd / TiO 2上2-吡喃酮的4-烷氧基和4-甲基衍生物转化为相应的二氢-或四氢吡喃酮是快速的并且提供了良好的产率和高ee。顺式-四氢吡喃酮的de含量为98-99％。ee可以通过动力学拆分进一步提高。
• Kava derived therapeutic compounds and methods of use thereof
  申请人：KUALITY HERBCEUTICS LLC

  公开号：US10624943B2

  公开（公告）日：2020-04-21

  Certain embodiments of the invention provide a composition comprising at least two compounds selected from the group consisting of dihydromethysticin, methysticin, dihydrokavain, kavain, desmethoxyyangonin and 11-methoxyyangonin, wherein the composition is substantially free of flavokawain B. Certain embodiments of the invention also provide a method for treating or preventing cancer in a mammal (e.g., a human) in need of such treatment comprising, administering to the mammal a carrier and a compound selected from the group consisting of dihydromethysticin, methysticin, dihydrokavain, kavain, desmethoxyyangonin and 11-methoxyyangonin, wherein the compound is substantially free of other kava extract components.

  本发明的某些实施方案提供了一种组合物，该组合物包含至少两种选自由二氢麦角苷、甲基麦角苷、二氢卡瓦胡椒素、卡瓦胡椒素、去甲氧基麦角苷和11-甲氧基麦角苷组成的组的化合物，其中该组合物基本上不含黄卡瓦胡椒素B、向哺乳动物施用载体和选自由二氢甲基芪烷素、甲基芪烷素、二氢卡瓦胡椒素、卡瓦胡椒素、去甲氧基卡瓦胡椒素和 11-甲氧基卡瓦胡椒素组成的组的化合物，其中该化合物基本上不含其他卡瓦提取物成分。
• KAVA DERIVED THERAPEUTIC COMPOUNDS AND METHODS OF USE THEREOF
  申请人：XING Chengguo

  公开号：US20160279184A1

  公开（公告）日：2016-09-29

  Certain embodiments of the invention provide a composition comprising at least two compounds selected from the group consisting of dihydromethysticin, methysticin, dihydrokavain, kavain, desmethoxyyangonin and 11-methoxyyangonin, wherein the composition is substantially free of flavokawain B. Certain embodiments of the invention also provide a method for treating or preventing cancer in a mammal (e.g., a human) in need of such treatment comprising, administering to the mammal a carrier and a compound selected from the group consisting of dihydromethysticin, methysticin, dihydrokavain, kavain, desmethoxyyangonin and 11-methoxyyangonin, wherein the compound is substantially free of other kava extract components.
• THERAPEUTIC COMPOUNDS AND METHODS OF USE THEREOF
  申请人：KUALITY HERBCEUTICS LLC

  公开号：US20180134679A1

  公开（公告）日：2018-05-17

  The invention provides compounds that are useful for treating or preventing cancer.
• [EN] KAVA DERIVED THERAPEUTIC COMPOUNDS AND METHODS OF USE THEREOF<br/>[FR] COMPOSÉS THÉRAPEUTIQUES ISSUS DU KAVA ET LEURS PROCÉDÉS D'UTILISATION
  申请人：KUALITY HERBCEUTICS LLC

  公开号：WO2015070226A1

  公开（公告）日：2015-05-14

  Certain embodiments of the invention provide a composition comprising at least two compounds selected from the group consisting of dihydromethysticin, methysticin, dihydrokavain, kavain, desmethoxyyangonin and 11-methoxyyangonin, wherein the composition is substantially free of flavokawain B. Certain embodiments of the invention also provide a method for treating or preventing cancer in a mammal (e.g., a human) in need of such treatment comprising, administering to the mammal a carrier and a compound selected from the group consisting of dihydromethysticin, methysticin, dihydrokavain, kavain, desmethoxyyangonin and 11-methoxyyangonin, wherein the compound is substantially free of other kava extract components.