gymnothelignan N | 1401068-90-3

• 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: gymnothelignan N
• 英文别名: (1R,12S,13S,14S)-2',6',9-trimethoxy-13,14-dimethylspiro[5,7,15-trioxatetracyclo[10.2.1.02,10.04,8]pentadeca-2,4(8),9-triene-11,4'-cyclohexa-2,5-diene]-1'-one
• CAS: 1401068-90-3
• 化学式: C₂₂H₂₄O₇
• 分子量: 400.428
• InChiKey: PNGZYPKURMIFBH-QCOQQOGRSA-N

物化性质

• 沸点：
  584.0±50.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  甲醇 、 gymnothelignan N 在 硫酸 作用下， 反应 1.0h， 以95%的产率得到gymnothelignan H
  参考文献：
  名称：

  Gymnothelignans A–O: Conformation and Absolute Configuration Analyses of Lignans Bearing Tetrahydrofuran from Gymnotheca chinensis

  摘要：

  Fifteen new lignans, gymnothelignans A-O (1-15), bearing tetrahydrofuran with variable conformations belonging to three potentially related skeletons were isolated from Gymnotheca chinensis Decne. The structures were elucidated by means of detailed spectroscopic analysis. Absolute configurations were assigned using X-ray single-crystal diffraction and chemical transformations. Moreover, by the homology, compounds 1-11 and eupomatilones were confirmed to have uniform R-configuration at C-5. However, a synthesized congener has long been mistaken as 5-epimer of eupomatilone-6. This work provides guidance for the absolute configuration establishment of the subeupomatilone family with trans-H-4 H-5 configuration.

  DOI：

  10.1021/jo301225v
• 作为产物：
  描述：

  在 六氟异丙醇 、 碘苯二乙酸 、 三氟化硼乙醚 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 0.84h， 生成 gymnothelignan N 、
  参考文献：
  名称：

  Gymnothelignan N、Beilschmin A 和 Eupomatilones 1、3、4 和 7 的不同全合成

  摘要：

  本报告详细介绍了gymnothelignan N 的七步不对称全合成。该方法基于早期的单碳同源内酯化反应，我们最近对其进行了重新审视和修改，以构建具有必需的 β,γ-邻位立体中心的核心 γ-丁内酯基序。通过设计，使用相同的手性 γ-丁内酯中间体允许从市售材料中通过五到六个步骤快速有效地组装光学活性的 eupomatilones 1、3、4 和 7。这代表了迄今为止报道的最短和最高产率的合成方法之一。

  DOI：

  10.1021/acs.joc.1c03167

文献信息

• Bioinspired Total Synthesis of Gymnothelignan N
  作者：Huilin Li、Yuanyuan Zhang、Xingang Xie、Haichen Ma、Changgui Zhao、Gaoyuan Zhao、Xuegong She

  DOI：10.1021/ol501960j

  日期：2014.9.5

  Bioinspired total synthesis of gymnothelignan N was accomplished in 13 steps and 6.7% overall yield. The synthesis features a syn Evans aldol reaction, an intramolecular hydrogenative dehydration reaction, and a phenol oxidative dearomatization/Friedel-Crafts reaction, which provides a new plausible biosynthetic pathway for the gymnothelignans and other symbiotic members. Meanwhile, another tetrahydrofuran-type lignan beilschmin A was also synthesized.
• Gymnothelignans A–O: Conformation and Absolute Configuration Analyses of Lignans Bearing Tetrahydrofuran from Gymnotheca chinensis
  作者：Dahai He、Lisheng Ding、Hongxi Xu、Xinxiang Lei、Hongping Xiao、Yan Zhou

  DOI：10.1021/jo301225v

  日期：2012.10.5

  Fifteen new lignans, gymnothelignans A-O (1-15), bearing tetrahydrofuran with variable conformations belonging to three potentially related skeletons were isolated from Gymnotheca chinensis Decne. The structures were elucidated by means of detailed spectroscopic analysis. Absolute configurations were assigned using X-ray single-crystal diffraction and chemical transformations. Moreover, by the homology, compounds 1-11 and eupomatilones were confirmed to have uniform R-configuration at C-5. However, a synthesized congener has long been mistaken as 5-epimer of eupomatilone-6. This work provides guidance for the absolute configuration establishment of the subeupomatilone family with trans-H-4 H-5 configuration.
• Divergent Total Syntheses of Gymnothelignan N, Beilschmin A, and Eupomatilones 1, 3, 4, and 7
  作者：Hosam Choi、Joohee Choi、Jongyeol Han、Kiyoun Lee

  DOI：10.1021/acs.joc.1c03167

  日期：2022.3.18

  same chiral γ-butyrolactone intermediate permitted the rapid and effective divergent assembly of optically active eupomatilones 1, 3, 4, and 7 in five or six steps from commercially available materials. This represents one of the shortest and highest-yielding syntheses reported to date.

  本报告详细介绍了gymnothelignan N 的七步不对称全合成。该方法基于早期的单碳同源内酯化反应，我们最近对其进行了重新审视和修改，以构建具有必需的 β,γ-邻位立体中心的核心 γ-丁内酯基序。通过设计，使用相同的手性 γ-丁内酯中间体允许从市售材料中通过五到六个步骤快速有效地组装光学活性的 eupomatilones 1、3、4 和 7。这代表了迄今为止报道的最短和最高产率的合成方法之一。