(1R,4aS,6S,7R,7aS)-6-Hydroxy-1-methoxy-7-methyl-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid | 88675-13-2

• 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,4aS,6S,7R,7aS)-6-Hydroxy-1-methoxy-7-methyl-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid
• CAS: 88675-13-2
• 化学式: C₁₁H₁₆O₅
• 分子量: 228.245
• InChiKey: JWCGOSTUOIAAJK-KHBMLBSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.59
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  75.99
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R,4aS,6S,7R,7aS)-6-Hydroxy-1-methoxy-7-methyl-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid 在 1-羟基苯并三唑 、 caesium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.67h， 生成 methyl (R)-2-((1R,4aS,6S,7R,7aS)-6‑hydroxy-1‑methoxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxamido)-3-(5-((4-nitrobenzyl)oxy)-1H-indol-3-yl)propanoate
  参考文献：
  名称：

  Bionic synthesis of novel monoterpenoid indole alkaloid-like analogs with tyrosinase inhibition activity based on loganetin

  摘要：

  DOI：

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

  Loganetin/1-Epiloganetin 在 盐酸 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 (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：

  Bionic synthesis of novel monoterpenoid indole alkaloid-like analogs with tyrosinase inhibition activity based on loganetin

  摘要：

  DOI：

  10.1016/j.molstruc.2024.138608

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。
• 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.