(1R)-1-O-methyl loganin aglycone | 68736-83-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R)-1-O-methyl loganin aglycone
• 英文别名: (-)-1-β-O-methyl loganin aglucone；methyl (1R,4aS,6S,7R,7aS)-6-hydroxy-1-methoxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
• CAS: 68736-83-4
• 化学式: C₁₂H₁₈O₅
• 分子量: 242.272
• InChiKey: PFBHTYXAPARNAL-XEVLOLMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R)-1-O-methyl loganin aglycone 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以92 %的产率得到(1R,4aS,6S,7R,7aS)-6-Hydroxy-1-methoxy-7-methyl-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid
  参考文献：
  名称：

  10.1016/j.molstruc.2024.138608

  摘要：

  DOI：

  10.1016/j.molstruc.2024.138608
• 作为产物：
  描述：

  7-O-benzoyl-1-O-methyl-loganin aglucone 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以98%的产率得到(1R)-1-O-methyl loganin aglycone
  参考文献：
  名称：

  Iridoids : enantioselective synthesis of loganin via an asymmetric diels-alder reaction

  摘要：

  DOI：

  10.1016/s0040-4020(01)87559-1

文献信息

• The bitter iridoids from Viburnum urceolatum
  作者：Tsunao Hase、Hideki Takao、Tetsuo Iwagawa

  DOI：10.1016/0031-9422(83)80027-2

  日期：——

  Abstract Four new bitter iridoid glucosides, including three bis-iridoids, were isolated from Viburnum urceolatum and their structures elucidated. They are composed of loganin or deoxyloganin as the aglucone esterified with either aromatic glucoside or with glucose in the 4-position.

  摘要 从紫薇中分离得到4个新的苦环烯醚萜苷，包括3个双环烯醚萜苷，并阐明了它们的结构。它们由马钱素或脱氧马钱素组成，作为用芳香糖苷或在 4 位上用葡萄糖酯化的配基。
• Gram-Scale Synthesis of Loganetin from <i>S</i>-(+)-Carvone
  作者：Xiangyu Zhuang、Chenghong Sun、Pengzhen Fu、Changhai Yu、Jie Jiang、Shuangshuang Wang、Xuefeng Xiao、Bin Wang

  DOI：10.1021/acs.joc.3c00253

  日期：2023.5.5

  aglycone moiety of loganin that has a 5,6-fused bicyclic framework and exhibits a wide range of interesting biological activities. A gram-scale synthesis of loganetin has been accomplished from the readily accessible S-(+)-carvone. The key reactions of the synthesis are a Favorskii rearrangement to introduce four stereocenters and a sulfuric acid-meditated deprotection/cyclization reaction to assemble the

  Loganetin 是马钱素的糖苷配基部分，具有 5,6-稠合双环框架并表现出广泛的有趣生物活性。已从易于获得的S -(+)-香芹酮中完成了 loganetin 的克级合成。合成的关键反应是 Favorskii 重排以引入四个立体中心和硫酸介导的脱保护/环化反应以组装具有完全立体选择性的敏感二氢吡喃环。这项工作还使我们能够成功合成 C1 甲氧基马钱子素和马钱子素的对映异构体。
• Modified iridoid glycosides as anti-implantation agents
  作者：Anju P Misra、Vijayavitthal T Mathad、Kanwal Raj、Amiya P Bhaduri、Rashmi Tiwari、Anuradha Srivastava、P.K Mehrotra

  DOI：10.1016/s0968-0896(01)00105-5

  日期：2001.11

  Structural modifications in iridoid glycosides and evaluation of their efficacy on adhering capability (in vitro) of immature hamster uterine epithelial cells to the substratum have been studied. Out of 31, eight compounds in vitro, five compounds in utero and two in vivo showed adhesion/implantation preventing activity, respectively. The results provide an indication for further exploration in the line of development of anti-adhesive agents. (C) 2001 Published by Elsevier Science Ltd.