5-[(1S,3aR,4S,6aR)-4-(3,4-二甲氧基苯基)-1,3,3a,4,6,6a-六氢呋喃并[4,3-c]呋喃-1-基]-1,3-苯并二氧戊环 | 36150-23-9

• 物质功能分类: 生物化工 - 提取物
• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 呋喃类木脂素
• 中文名称: 5-[(1S,3aR,4S,6aR)-4-(3,4-二甲氧基苯基)-1,3,3a,4,6,6a-六氢呋喃并[4,3-c]呋喃-1-基]-1,3-苯并二氧戊环
• 中文别名: 去甲槟郎碱
• 英文名称: methyl piperitol
• 英文别名: Kobusin；5-[(3S,3aR,6S,6aR)-6-(3,4-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-1,3-benzodioxole
• CAS: 36150-23-9
• 化学式: C₂₁H₂₂O₆
• 分子量: 370.402
• InChiKey: AWOGQCSIVCQXBT-VUEDXXQZSA-N

物化性质

• 沸点：
  506.4±50.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (R)-4-{(R)-[(tert-butyldimethylsilyl)oxy](3,4-dihydroxyphenyl)methyl}dihydrofuran-2(3H)-one 在 sodium tetrahydroborate 、 caesium carbonate 、 乙酰氯 、 calcium chloride 、 lithium hexamethyldisilazane 、 原甲酸三甲酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.75h， 生成 5-[(1S,3aR,4S,6aR)-4-(3,4-二甲氧基苯基)-1,3,3a,4,6,6a-六氢呋喃并[4,3-c]呋喃-1-基]-1,3-苯并二氧戊环
  参考文献：
  名称：

  Stereocontrolled Total Syntheses of Optically Active Furofuran Lignans

  摘要：

  Plant products (+)-sesamin, (+)-sesaminol, (+)-methylpiperitol, (+)-aschantin, and (+)-5'-hydroxymethylpiperitol were synthesized in a highly stereocontrolled manner through L-proline-catalyzed bifunctional-urea-accelerated cross-aldol reaction, followed by biomimetic construction of the furofuran lignan skeleton through a quinomethide intermediate.

  DOI：

  10.1055/s-0034-1378812

文献信息

• A new stereocontrolled synthesis of diequatorial furofuran lignans having two different aryl groups: A synthesis of methyl piperitol
  作者：Tsuyoshi Ogiku、Shin-ichi Yoshida、Masami Takahashi、Tooru Kuroda、Hiroshi Ohmizu、Tameo Iwasaki

  DOI：10.1016/s0040-4039(00)60113-2

  日期：1992.7

  Methyl piperitol, a representative example of the diequatorial furofuran lignans, was synthesized in a good overall yield based on a highly stereocontrolled tandem Michael addition-aldol reaction.

  基于高度立体控制的串联迈克尔加成-醛醇缩合反应，以良好的总收率合成了甲基哌啶醇，它是二氟呋喃呋喃木脂素的代表性实例。
• A sterically encumbered photoredox catalyst enables the unified synthesis of the classical lignan family of natural products
  作者：Edwin Alfonzo、Aaron B. Beeler

  DOI：10.1039/c9sc02682g

  日期：——

  selectively generate carbonyl ylides from electron-rich epoxides. These can undergo concerted [3 + 2] dipolar cycloadditions to afford tetrahydrofurans, which were advanced (2–4 steps) to at least one representative natural product or natural product scaffold within all six subtypes in classical lignans. The application of those synthetic blueprints to the synthesis of heterolignans bearing unnatural

  在这里，我们详细介绍了经典的天然木脂素家族天然产品的统一合成方法，该方法取决于与从自然界生物合成蓝图战略性确定的常见中间体的差异。通过会聚和模块化方法来尝试访问通用中间体的努力导致发现了一种空间受限的光氧化还原催化剂，该催化剂可以从富含电子的环氧化物中选择性地生成羰基化物。这些可以经历一致的[3 + 2]偶极环加成反应，得到四氢呋喃，在经典木脂素的所有六种亚型中，四氢呋喃被推进（2-4个步骤）至至少一种代表性的天然产物或天然产物支架。证明了这些合成蓝图在具有不自然功能的杂木聚糖合成中的应用，
• Short and Stereoselective Total Synthesis of (±)-Dihydrosesamin and (±)-Acuminatin Methyl Ether by Radical Cyclisation of Epoxides Using a Transition-Metal Radical Source
  作者：Kalyan Kumar Rana、Chandrani Guin、Subhas Chandra Roy

  DOI：10.1055/s-2001-16041

  日期：——

  Short, efficient and stereoselective synthesis of a furano lignans, (±)-Dihydrosesamin and (±)-Acuminatin Methyl Ether has been achieved in good overall yield through the radical cyclisation of epoxides using a Ti(III) reagent as the radical initiator.

  使用 Ti(III) 试剂作为自由基引发剂，通过环氧化物的自由基环化，以良好的总收率实现了呋喃木脂素、(±)-二氢芝麻素和 (±)-Acuminatin 甲基醚的快速、高效和立体选择性合成。
• Short and Stereoselective Total Synthesis of Furano Lignans (±)-Dihydrosesamin, (±)-Lariciresinol Dimethyl Ether, (±)-Acuminatin Methyl Ether, (±)-Sanshodiol Methyl Ether, (±)-Lariciresinol, (±)-Acuminatin, and (±)-Lariciresinol Monomethyl Ether and Furofuran Lignans (±)-Sesamin, (±)-Eudesmin, (±)-Piperitol Methyl Ether, (±)-Pinoresinol, (±)-Piperitol, and (±)-Pinoresinol Monomethyl Ether by Radical Cyclization of Epoxides Using a Transition-Metal Radical Source
  作者：Subhas Chandra Roy、Kalyan Kumar Rana、Chandrani Guin

  DOI：10.1021/jo010857u

  日期：2002.5.1

  corresponding cyclized products. The furofuran lignans sesamin 2a, eudesmin 2b, and piperitol methyl ether 2e were also prepared directly by using the same precursors 4a-f on radical cyclization followed by treatment with iodine and pinoresinol 2h, piperitol 2i, and pinoresinol monomethyl ether 2j after controlled hydrogenolysis of the benzyl protecting group of the corresponding cyclized products. Two

  使用双（环戊二烯基）钛（III）作为自由基源，对适当取代的环氧醚4a-g进行分子内自由基环化，生成三取代的四氢呋喃呋喃木脂素和2,6-二芳基-3,7-二氧杂双环[3.3.0]辛烷木脂素，具体取决于在反应条件上。钛（III）物种由可商购的二茂钛二氯化物和THF中的活化锌粉原位制备。自由基环化后进行酸性后处理，环氧烯烃醚4a-g直接提供呋喃诺木脂素二氢芝麻素1a，lariciresinol二甲醚1b，acuminatin甲基醚1e和sanshodiol甲基醚1g，并分别提供lariciresinol 1h，acuminatin 1i和去除lariciresinol的单甲醚1通过控制相应的环化产物的氢解来保护苄基保护基。呋喃呋喃木脂素芝麻素2a，爱德敏2b和胡椒醇甲基醚2e也可以通过在自由基环化反应中使用相同的前体4a-f，然后在碘化氢的受控氢解后，用碘和松脂醇2h，胡椒醇2i和松脂醇单甲醚2j
• Pharmaceutical composition for preventing and treating chronic obstructive lung disease containing, as active ingredient, Magnoliae flos extract, fraction, or active fraction thereof
  申请人：KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY

  公开号：US10376553B2

  公开（公告）日：2019-08-13

  A pharmaceutical composition includes any of an extract of Magnoliae flos, a fraction or an active fraction obtained by fractionation thereof with an organic solvent, and a compound separated therefrom as an active ingredient. The extract of Magnoliae flos, the fraction or the active fraction obtained by fractionation thereof with an organic solvent, or the compound separated therefrom inhibits the expression of MUC5AC induced by TNF-α and the promoter activity in human lung cancer mucosal cells (H292), reduces the number of inflammatory cells in the bronchoalveolar lavage fluid of the chronic obstructive pulmonary disease mouse model, inhibits the production of reactive oxygen species, and reduces the cytokines; and therefore are effective in preventing or treating chronic obstructive pulmonary disease.

  一种药物组合物包括作为活性成分的厚朴提取物、用有机溶剂分馏得到的馏分或活性馏分以及从中分离出的化合物中的任意一种。厚朴提取物、用有机溶剂分馏得到的馏分或活性馏分或从中分离得到的化合物可抑制 TNF-α 诱导的 MUC5AC 的表达和人肺癌粘膜细胞（H292）的启动子活性，减少慢性阻塞性肺病小鼠模型支气管肺泡灌洗液中炎性细胞的数量，抑制活性氧的产生，减少细胞因子；因此可有效预防或治疗慢性阻塞性肺病。