2-((5S,7S)-1,1,7-Trimethyl-6-methylene-2,3,4,5,6,7,8,9-octahydro-1H-benzocyclohepten-5-yl)-benzene-1,4-diol

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-((5S,7S)-1,1,7-Trimethyl-6-methylene-2,3,4,5,6,7,8,9-octahydro-1H-benzocyclohepten-5-yl)-benzene-1,4-diol
• 英文别名: Frondosin A；2-[(5S,7S)-1,1,7-trimethyl-6-methylidene-3,4,5,7,8,9-hexahydro-2H-benzo[7]annulen-5-yl]benzene-1,4-diol
• 化学式: C₂₁H₂₈O₂
• 分子量: 312.452
• InChiKey: MISNKONIRLZVLE-RBZFPXEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-((5S,7S)-1,1,7-Trimethyl-6-methylene-2,3,4,5,6,7,8,9-octahydro-1H-benzocyclohepten-5-yl)-benzene-1,4-diol 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以4.5 mg的产率得到(5S,7S)-5-(2,5-Dimethoxy-phenyl)-1,1,7-trimethyl-6-methylene-2,3,4,5,6,7,8,9-octahydro-1H-benzocycloheptene
  参考文献：
  名称：

  Frondosins, five new sesquiterpene hydroquinone derivatives with novel skeletons from the sponge Dysidea frondosa: Inhibitors of interleukin-8 receptors

  摘要：

  Bioassay-guided Fractionation of the EtOAc extract of the sponge Dysidea frondosa collected in Pohnpei yielded five sesquiterpenes, frondosins A-E (1-5). The structures and relative stereochemistry of the frondosins were established by interpretation of spectral data. Frondosins A-E (1-5), which possess novel carbon skeletons, were found to be inhibitors of interleukin-8 receptors and protein kinase C in the low micromolar range. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00205-6

文献信息

• Methods and compositions for terpenoid tricycloalkane synthesis
  申请人：University of Florida Research Foundation, Inc.

  公开号：US10287239B1

  公开（公告）日：2019-05-14

  In one aspect, the disclosure relates to methods for preparation of intermediates useful for the preparation of terpenoid cores. In a further aspect, the disclosed methods pertain to the preparation of compounds comprising a terpenoid core or scaffold, such as 6/7/5 tricycloalkanes. The disclosed methods utilize abundant starting materials and simple reaction sequences that can be used to tunably and scalably assemble common terpenoid cores. In various aspects, the present disclosure pertains to compounds prepared using the disclosed methods. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present disclosure.

  在一个方面，本公开涉及用于制备对萜类核心的制备有用的中间体的方法。在另一个方面，所公开的方法涉及制备包括萜类核心或支架的化合物，例如6/7/5三环脂环烷。所公开的方法利用丰富的起始材料和简单的反应序列，可用于可调和可扩展地组装常见的萜类核心。在各个方面，本公开涉及使用所公开方法制备的化合物。本摘要旨在作为搜索特定领域的扫描工具，并不意味着对本公开的限制。
• [EN] METHODS AND COMPOSITIONS FOR TERPENOID SYNTHESIS<br/>[FR] PROCÉDÉS ET COMPOSITIONS POUR LA SYNTHÈSE DE TERPÉNOÏDES
  申请人：UNIV FLORIDA

  公开号：WO2018053322A1

  公开（公告）日：2018-03-22

  In one aspect, the disclosure relates to methods for preparation of terpene and terpene-like molecules. In a further aspect, the disclosure relates to the products of the disclosed methods, i.e., terpene and terpene-like molecules prepared using the disclosed methods. Intermediates for the synthesis of a wide variety of terpenoids are γ-allyl Knoevenagel adducts or quasi γ-allyl Knoevenagel adducts are disclosed. In various aspects, methods of preparing terpenoids through these intermediates are disclosed. The methods can comprise α-alkylation of an allylic electrophile followed by ring-closure metathesis to a polycyclic terpenoid structure. In a further aspect, the disclosure pertains to terpenoid frameworks, and compounds prepared via disclosed oxidation and substitution reactions on the disclosed terpenoid frameworks. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present disclosure.

  在一个方面，本公开涉及制备萜烯和类萜烯分子的方法。在另一个方面，本公开涉及所述方法的产物，即使用所述方法制备的萜烯和类萜烯分子。公开了合成各种萜烯类化合物的中间体γ-烯丙基Knoevenagel加合物或准γ-烯丙基Knoevenagel加合物。在各个方面，公开了通过这些中间体制备萜烯类化合物的方法。这些方法可以包括烯丙基亲电试剂的α-烷基化，然后通过环闭合重排生成多环萜烯结构。在另一个方面，本公开涉及萜烯类骨架，以及通过公开的氧化和取代反应在所述萜烯类骨架上制备的化合物。本摘要旨在作为在特定领域进行搜索的扫描工具，并不旨在限制本公开。
• METHODS AND COMPOSITIONS FOR TERPENOID SYNTHESIS
  申请人：University of Florida Research Foundation, Inc.

  公开号：US20190270700A1

  公开（公告）日：2019-09-05

  In one aspect, the disclosure relates to methods for preparation of terpene and terpene-like molecules. In a further aspect, the disclosure relates to the products of the disclosed methods, i.e., terpene and terpene-like molecules prepared using the disclosed methods. Intermediates for the synthesis of a wide variety of terpenoids are γ-allyl Knoevenagel adducts or quasi γ-allyl Knoevenagel adducts are disclosed. In various aspects, methods of preparing terpenoids through these intermediates are disclosed. The methods can comprise a-alkylation of an allylic electrophile followed by ring-closure metathesis to a polycyclic terpenoid structure. In a further aspect, the disclosure pertains to terpenoid frameworks, and compounds prepared via disclosed oxidation and substitution reactions on the disclosed terpenoid frameworks. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present disclosure.
• METHODS AND COMPOSITIONS FOR TERPENOID TRICYCLOALKANE SYNTHESIS
  申请人：University of Florida Research Foundation, Inc.

  公开号：US20190352254A1

  公开（公告）日：2019-11-21

  In one aspect, the disclosure relates to methods for preparation of intermediates useful for the preparation of terpenoid cores. In a further aspect, the disclosed methods pertain to the preparation of compounds comprising a terpenoid core or scaffold, such as 6/7/5 tricycloalkanes. The disclosed methods utilize abundant starting materials and simple reaction sequences that can be used to tunably and scalably assemble common terpenoid cores. In various aspects, the present disclosure pertains to compounds prepared using the disclosed methods. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present disclosure.
• Frondosins, five new sesquiterpene hydroquinone derivatives with novel skeletons from the sponge Dysidea frondosa: Inhibitors of interleukin-8 receptors
  作者：Ashok D. Patil、Alan J Freyer、Lew Killmer、Priscilla Offen、Brad Carte、Anthony J. Jurewicz、Randall K. Johnson

  DOI：10.1016/s0040-4020(97)00205-6

  日期：1997.4

  Bioassay-guided Fractionation of the EtOAc extract of the sponge Dysidea frondosa collected in Pohnpei yielded five sesquiterpenes, frondosins A-E (1-5). The structures and relative stereochemistry of the frondosins were established by interpretation of spectral data. Frondosins A-E (1-5), which possess novel carbon skeletons, were found to be inhibitors of interleukin-8 receptors and protein kinase C in the low micromolar range. (C) 1997 Elsevier Science Ltd.