Anhydropterosin C | 57283-34-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: Anhydropterosin C
• 英文别名: 6-(2-Hydroxyethyl)-2,5,7-trimethylinden-1-one
• CAS: 57283-34-8
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: LLPPZAOWAGVIIJ-UHFFFAOYSA-N

物化性质

• 沸点：
  409.2±45.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Anhydropterosin C 在 四氧化锇 、 硫酸 作用下， 以 吡啶 为溶剂， 反应 2.5h， 生成 (3aR,8aR)-6-(2-Hydroxy-ethyl)-2,2,5,7,8a-pentamethyl-3a,8a-dihydro-indeno[1,2-d][1,3]dioxol-8-one
  参考文献：
  名称：

  Tanaka, Nobutoshi; Satake, Toshiko; Takahashi, Akira, Chemical and pharmaceutical bulletin, 1982, vol. 30, # 10, p. 3640 - 3646

  摘要：

  DOI：
• 作为产物：
  描述：

  蕨素 C 在 硫酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以33 mg的产率得到Anhydropterosin C
  参考文献：
  名称：

  Tanaka, Nobutoshi; Satake, Toshiko; Takahashi, Akira, Chemical and pharmaceutical bulletin, 1982, vol. 30, # 10, p. 3640 - 3646

  摘要：

  DOI：

文献信息

• Final-Stage Site-Selective Acylation for the Total Syntheses of Multifidosides A-C
  作者：Yoshihiro Ueda、Takumi Furuta、Takeo Kawabata

  DOI：10.1002/anie.201504729

  日期：2015.10.5

  The first total syntheses of multifidosides A–C have been achieved. The synthetic strategy is characterized by catalytic site‐selective acylation of unprotected glycoside precursors in the final stage of the synthesis. High functional‐group tolerance of the site‐selective acylation, promoted by an organocatalyst, enabled the conventionally difficult molecular transformation in a predictable and reliable

  首次实现了多元醇A–C的全部合成。合成策略的特点是在合成的最后阶段对未保护的糖苷前体进行催化位点选择性酰化。由有机催化剂促进的对位点选择性酰化反应的高官能团耐受性使常规困难的分子转化能够以可预测和可靠的方式进行。该策略的优点是避免了在总合成的最后阶段去除保护基期间发生不希望的副反应的风险。
• An efficient synthesis of pterosin C and other pterosins
  作者：Kam-Mui Eva Ng、Trevor C. McMorris

  DOI：10.1139/v84-334

  日期：1984.10.1

  A versatile synthetic route to pterosins, sesquiterpenoid indanones present in bracken, Pteridiumaquilinum, has been developed. The route is exemplified by the synthesis of (2S,3S)-pterosin C by Friedel–Crafts bisacylation of the methyl ether of 2-(2,6-dimethylphenyl)ethanol with methylmalonyl chloride. Demethylation of the resulting 1,3-indandione and reduction with zinc and acetic acid in the presence of acetic anhydride and sodium acetate afforded a mixture of racemic cis and trans isomers of pterosin C diacetate, which was hydrolysed to the corresponding pterosins. Separation and resolution via the S-(+)-α-phenylbutyric esters gave (2S,3S)-pterosin C and (2R,3R)-pterosin C. Other pterosins were prepared as racemates from the 1,3-indandione.

  已经开发出了一种通用的合成途径来制备蕨类植物中存在的对位香豆素类化合物——翅果酸，具体来说就是欧洲蕨（Pteridium aquilinum）。该合成途径的示例是通过使用甲基丙烯酸氯对2-(2,6-二甲基苯基)乙醇的甲基醚进行弗里德尔-克拉夫茨双取代反应来合成(2S,3S)-翅果酸C。将得到的1,3-茚二酮脱甲基，并在乙酸和乙酸钠的存在下用锌和乙酸还原，得到了翅果酸C二醋酸酯的消旋顺式和反式异构体的混合物，该混合物经水解得到了相应的翅果酸。通过S-(+)-α-苯基丁酸酯的分离和解析，得到了(2S,3S)-翅果酸C和(2R,3R)-翅果酸C。其他翅果酸则是从1,3-茚二酮以消旋混合物的形式制备的。

• Structure-activity relationships of illudins: analogs with improved therapeutic index.
  作者：Trevor C. McMorris、Michael J. Kelner、Wen Wang、Leita A. Estes、Mark A. Montoya、Raymond Taetle

  DOI：10.1021/jo00051a037

  日期：1992.12

  Illudin S and M are extremely toxic sesquiterpenes produced by Omphalotus illudens. At low pH they behave as bifunctional alkylating agents, but at physiological pH they do not react with oxygen or nitrogen nucleophiles. Illudins react spontaneously with sulfur nucleophiles, glutathione or cysteine, at or slightly below pH 7, and toxicity to HL 60 cells can be modulated by altering glutathione levels in cells. Analogs of illudin M, e.g. the deoxy and, particularly, the dehydro derivatives, are less reactive to thiols and correspondingly less toxic to HL 60 cells than the parent compound. Dehydroilludin M has been found to be quite effective at inhibiting tumor growth in vivo at doses well tolerated by athymic nude mice.
• Isolation and structure of wallichoside, a novel pteroside from Pteris wallichiana
  作者：Pasupati Sengupta、Manju Sen、Sushil Kumar Niyogi、Satyesh Chandra Pakrashi、Esahak Ali

  DOI：10.1016/s0031-9422(00)84388-5

  日期：1976.1
• Murakami,T. et al., Chemical and pharmaceutical bulletin, 1976, vol. 24, # 1, p. 173 - 175
  作者：Murakami,T. et al.

  DOI：——

  日期：——