(1S-(1alpha,3aalpha,4beta,6aalpha))-5-(4-(3,4-二甲氧基苯基)四氢-1H,3H-呋喃并(3,4-c)呋喃-1-基)-1,3-苯并二氧戊环 | 68296-27-5

• 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: (1S-(1alpha,3aalpha,4beta,6aalpha))-5-(4-(3,4-二甲氧基苯基)四氢-1H,3H-呋喃并(3,4-c)呋喃-1-基)-1,3-苯并二氧戊环
• 英文名称: (+)-fargesin
• 英文别名: 5-[(3S,3aR,6R,6aR)-6-(3,4-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-1,3-benzodioxole
• CAS: 68296-27-5
• 化学式: C₂₁H₂₂O₆
• 分子量: 370.402
• InChiKey: AWOGQCSIVCQXBT-LATRNWQMSA-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：

  (3R,4S)-4-(1,3-benzodioxol-5-ylcarbonyl)-3-[(R)-1-(3,4-dimethoxyphenyl)-1-hydroxymethyl]tetrahydro-2-furanone 在 吡啶 、 lithium aluminium tetrahydride 、 L-Selectride 、 甲基磺酰氯 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (1S-(1alpha,3aalpha,4beta,6aalpha))-5-(4-(3,4-二甲氧基苯基)四氢-1H,3H-呋喃并(3,4-c)呋喃-1-基)-1,3-苯并二氧戊环
  参考文献：
  名称：

  具有两个不同芳基的轴-赤道呋喃呋喃木脂素的立体控制新合成：Fargesin的合成

  摘要：

  Fargesin是轴-赤道呋喃呋喃木脂素的代表实例，是基于一种新的方法将C-4为1的立体化学进行了合成，以较高的总收率合成了Fargesin 。

  DOI：

  10.1016/s0040-4039(00)60114-4

文献信息

• C−H Insertion Approach to the Synthesis of <i>e</i><i>ndo,</i><i>e</i><i>xo</i>-Furofuranones:  Synthesis of (±)-Asarinin, (±)-Epimagnolin A, and (±)-Fargesin
  作者：Richard C. D. Brown、Carole J. R. Bataille、Gordon Bruton、Jeremy D. Hinks、Nigel A. Swain

  DOI：10.1021/jo015829q

  日期：2001.10.1

  A series of novel 5-aryl-4-aryloxymethyl-3-diazotetrahydrofuran-2-ones (12, 24, and 35a/b) have been prepared and found to undergo regio- and stereoselective C-H insertion reactions to afford 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane-8-ones (18, 26, and 36a/b) with endo,exo stereochemistry. Subsequent reduction of the lactone ring and cyclization of the resulting diols 27 and 37a/b permitted the synthesis

  已经制备了一系列新颖的5-芳基-4-芳氧基甲基-3-重氮四氢呋喃-2-酮（12、24和35a / b），发现它们进行了区域和立体选择性CH插入反应，从而得到2,6-二芳基具有内，外立体化学反应的-3,7-二氧杂双环[3.3.0]辛烷-8-酮（18、26和36a / b）。随后内酯环的还原和所得二醇27和37a / b的环化，可以合成三种内生的呋喃呋喃木聚糖内酯：天麻素（2），fargesin（3）和表甘露聚糖A（4）。在生产关键的重氮化合物24和35a / b的过程中，开发了一种改进的Ghosez酮亚胺-烯烃环化方法，该方法需要最大程度地减少酸敏感性官能团（例如存在于苯酚中的富电子苄基醚）的分解目标化合物2-4。
• A novel asymmetric synthesis of axial-equatorial furofuran lignans: A synthesis of (+)-fargesin
  作者：Shin-ichi Yoshida、Takeshi Yamanaka、Tutomu Miyake、Yasunori Moritani、Hiroshi Ohmizu、Tameo Iwasaki

  DOI：10.1016/0040-4039(95)01507-e

  日期：1995.10

  (+)-Fargesin (6), a representative example of the axial-equatorial furofuran lignans having two different aryl groups, was efficiently synthesized based on a highly diastereoselective Michael addition reaction of the cyanohydrin 1 to methyl (S)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-cis-2-propenoate (2).

  （+）-Fargesin（6）是一个典型的轴-赤道型呋喃木质素类化合物的代表，具有两个不同的芳香基团。它已通过一种高对映选择性的迈克尔加成反应高效合成，其中氰基水合物1与甲基（S）-3-（2,2-二甲基-1,3-二氧杂环戊烷-4-基）顺式-2-丙烯酸酯（2）发生反应。
• 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。
• Asymmetric syntheses of lignans utilizing novel diastereoselective Michael addition of cyanohydrin: Syntheses of (+)-fargesin and (−)-picropodophyllone
  作者：Shin-ichi Yoshida、Takeshi Yamanaka、Tutomu Miyake、Yasunori Moritani、Hiroshi Ohmizu、Tameo Iwasaki

  DOI：10.1016/s0040-4020(97)00643-1

  日期：1997.7

  The Michael addition reaction of lithium salt of cyanohydrin to (S)- and (R)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-cis-2-propenoate (2 and 3) proceeded in 93% de in the presence of two equivalents of HMPA at -100 degrees C. This diastereoselectivity could be elucidated by the stereocontrol based on the 1,3-allylic strain. Utilizing this reaction, stereocontrolled syntheses of (+)-fargesin (6) and (-)-picropodophyllone (7) were achieved. (C) 1997 Elsevier Science Ltd.
• First Stereocontrolled Syntheses of Unsymmetrically Substituted Bislactone Lignans:  Stereocontrolled Syntheses of Four Possible Isomers of Methyl 4,8-Dioxoxanthoxylol
  作者：Shin-ichi Yoshida、Tsuyoshi Ogiku、Hiroshi Ohmizu、Tameo Iwasaki

  DOI：10.1021/jo961733y

  日期：1997.3.1

  An efficient method for stereocontrolled syntheses of the unsymmetrically substituted bislactone subgroup of the furofuran lignan has been developed based on a stereoselective aldol reaction of the acid anhydride 8 or 9 and an aromatic aldehyde employing methyl 4,8-dioxoxanthoxylol (1a), 4,8-dioxofargesin (1b), methyl 4,8-dioxopiperitol (2a) and their isomer 3a as the representative examples of the axial-equatorial 1, diequatorial 2, and diaxial 3 types of this series.