(8E)-3,4,5,17,18,19-hexamethoxy-11-oxatetracyclo[13.4.0.02,7.09,13]nonadeca-1(19),2,4,6,8,15,17-heptaen-10-one | 110397-81-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: (8E)-3,4,5,17,18,19-hexamethoxy-11-oxatetracyclo[13.4.0.02,7.09,13]nonadeca-1(19),2,4,6,8,15,17-heptaen-10-one
• CAS: 110397-81-4；143564-17-4；146236-35-3
• 化学式: C₂₄H₂₆O₈
• 分子量: 442.466
• InChiKey: SRCRHVPJJGDDMQ-OVCLIPMQSA-N

物化性质

• 沸点：
  644.3±55.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (8E)-3,4,5,17,18,19-hexamethoxy-11-oxatetracyclo[13.4.0.02,7.09,13]nonadeca-1(19),2,4,6,8,15,17-heptaen-10-one 在 二异丁基氢化铝 作用下， 生成
  参考文献：
  名称：

  具有自然构型的异五味子立体选择性立体合成

  摘要：

  完成具有天然构型的异五味子素1的全合成，以明确的方式证实1的结构。从光学纯的9开始，以良好的产率获得烯丙醇11，然后将其立体选择性地转化为环氧化物12。最后，减少C ＝ O键裂变，得到了异五味子素1的天然对映异构体。

  DOI：

  10.1016/s0957-4166(00)80159-7
• 作为产物：
  描述：

  3,4,5-trimethoxybenzyl-4-butanolide 在 iron(III) perchlorate 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (8E)-3,4,5,17,18,19-hexamethoxy-11-oxatetracyclo[13.4.0.02,7.09,13]nonadeca-1(19),2,4,6,8,15,17-heptaen-10-one
  参考文献：
  名称：

  光学纯的gomisin A和五味子素的合成：具有天然结构的gomisin A和五味子素的第一个全合成

  摘要：

  首次完成了具有天然构型的gomisin A和五味子素的全合成。这些合成的关键特征是中间体9和21的高效分子内氧化偶联，可以以光学纯形式的两种对映异构体形式获得。操纵7和22的内酯部分可得到五味子素和gomisin A的天然对映体。

  DOI：

  10.1016/s0040-4039(00)74679-x

文献信息

• A practical method for the oxidative coupling of aromatic compounds
  作者：Masahide Tanaka、Hiroshi Mitsuhashi、Takeshi Wakamatsu

  DOI：10.1016/s0040-4039(00)74678-8

  日期：1992.7

  A practical method for the oxidative coupling reaction of phenolic and nonphenolic compounds is described. The versatility of this reaction was demonstrated by the successful coupling of the wide variety of substrates including catecholic compounds and known intermediates for the synthesis of steganacin and its analogs.

  描述了一种用于酚和非酚化合物的氧化偶联反应的实用方法。该反应的多功能性通过多种底物的成功偶联而得以证明，其中包括儿茶酚化合物和合成甜菊酸及其类似物的已知中间体。
• ATR INHIBITOR
  申请人：Niigata TLO Corporation

  公开号：EP1946757A1

  公开（公告）日：2008-07-23

  The present invention is to provide ATR inhibitor containing tricyclic compound including Schizandrins and Gomisins as an active constituent, useful for an inhibitor of ATR protein kinase.

  本发明旨在提供一种 ATR 抑制剂，其活性成分中含有三环化合物，包括 Schizandrins 和 Gomisins，可用于 ATR 蛋白激酶抑制剂。
• Synthesis of Optically Pure Gomisi Lignans: The Total Synthesis of (+)-Schizandrin, (+)-Gomisin A, and (+)-Isoschizandrin in Naturally Occurring Forms
  作者：Masahide Tanaka、Chieko Mukaiyama、Hiroshi Mitsuhashi、Masao Maruno、Takeshi Wakamatsu

  DOI：10.1021/jo00119a010

  日期：1995.7

  The total syntheses of (+)-schizandrin (1), (+)-gomisin A (2), and (+)-isoschizandrin (3) having natural configurations were accomplished. Optically pure butyrolactones ((-)-9, (-)-31) were transformed to alpha-benzylidenebutyrolactones ((+)-10, (+)-32, (+)-35). By a highly efficient iron(III) perchlorate-mediated oxidative coupling reaction of 10, 32, and 35, the key intermediates with biphenyl skeletons ((-)-11, (-)-33) were constructed with high stereoselectivity. Several methods for the stereoselective introduction of the C6-hydroxyl group were examined. For the synthesis of schizandrin and gomisin A, the Mukaiyama hydration reaction of(-)-11 and (-)-33 provided the desired products with satisfactory selectivity. For the synthesis of isoschizandrin, the stereoselective epoxidation of allylic alcohol (+)-48 was successfully utilized taking advantage of its conformational features.
• ATR Inhibitor
  申请人：Nishida Hiroshi

  公开号：US20100048923A1

  公开（公告）日：2010-02-25

  The present invention is to provide ATR inhibitor containing tricyclic compound including Schizandrins and Gomisins as an active constituent, useful for an inhibitor of ATR protein kinase.
• The stereoselective first total synthesis of isoschizandrin having the natural configuration
  作者：Masahide Tanaka、Hiroyuki Itoh、Hiroshi Mitsuhashi、Masao Maruno、Takeshi Wakamatsu

  DOI：10.1016/s0957-4166(00)80159-7

  日期：1993.4

  The total synthesis of isoschizandrin 1 having the natural configuration was accomplished confirming the structure of 1 in unambiguous manner. Starting from optically pure 9, allylic alcohol 11 was obtained in good yield, and was then converted into epoxide 12 stereoselectively. Finally, reducuve CO bond fission afforded the natural enantiomer of isoschizandrin 1.

  完成具有天然构型的异五味子素1的全合成，以明确的方式证实1的结构。从光学纯的9开始，以良好的产率获得烯丙醇11，然后将其立体选择性地转化为环氧化物12。最后，减少C ＝ O键裂变，得到了异五味子素1的天然对映异构体。