clusiacyclol A

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: clusiacyclol A
• 英文别名: [(1S,9S,12R,14S)-3,5-dihydroxy-9,13,13-trimethyl-8-oxatetracyclo[7.4.1.02,7.012,14]tetradeca-2(7),3,5-trien-4-yl]-phenylmethanone
• 化学式: C₂₃H₂₄O₄
• 分子量: 364.441
• InChiKey: BQIVXBUAUNSLAJ-KKIPCARGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  柠檬醛 在 哌啶 、 aluminum (III) chloride 、 乙酸酐 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 19.25h， 生成 clusiacyclol A
  参考文献：
  名称：

  Total Syntheses of Cannabicyclol, Clusiacyclol A and B, Iso-Eriobrucinol A and B, and Eriobrucinol

  摘要：

  Total syntheses of a series of chromane natural products that contain a cyclobutane ring are described. A unified theme In the strategy employed for all these syntheses Is an oxa-[3 + 3] annulation for constructing the chromane nucleus and a stepwise cationic [2 + 2] cycloaddition for the cyclobutane formation. More Importantly, the two reactions could be rendered in tandem, thereby providing an expeditious approach to this family of natural products.

  DOI：

  10.1021/ol401335u

文献信息

• A Facile Phenol-Driven Intramolecular Diastereoselective Thermal/Base-Catalyzed Dipolar [2 + 2] Annulation Reactions:  An Easy Access to Complex Bioactive Natural and Unnatural Benzopyran Congeners
  作者：Mukulesh Mondal、Vedavati G. Puranik、Narshinha P. Argade

  DOI：10.1021/jo0624344

  日期：2007.3.1

  phenol-driven intramolecular diastereoselective thermal/base-catalyzed dipolar [2 + 2] cycloaddition reactions and three different thermal intramolecular cyclization reactions. The effects of the nature and the position of phenolic groups in the starting materials on the course of these cycloaddition reactions have also been described. Depending upon the absence or presence of intramolecular hydrogen bonding

  复杂的具有生物活性的天然和非天然苯并吡喃同类物已通过苯酚驱动，通过两种不同的二羟基邻苯二酚，天然间苯二酸衍生物和三羟基二苯甲酮与柠檬醛和/或法呢醛的反应，以非常好的收率合成了一步/两步法。分子内非对映选择性热/碱催化偶极[2 + 2]环加成反应和三种不同的分子内热环化反应。还描述了原料中酚基的性质和位置对这些环加成反应过程的影响。取决于原料中酚基团与羰基部分的分子内氢键是否存在，
• Total Syntheses of Cannabicyclol, Clusiacyclol A and B, Iso-Eriobrucinol A and B, and Eriobrucinol
  作者：Hyun-Suk Yeom、Hui Li、Yu Tang、Richard P. Hsung

  DOI：10.1021/ol401335u

  日期：2013.6.21

  Total syntheses of a series of chromane natural products that contain a cyclobutane ring are described. A unified theme In the strategy employed for all these syntheses Is an oxa-[3 + 3] annulation for constructing the chromane nucleus and a stepwise cationic [2 + 2] cycloaddition for the cyclobutane formation. More Importantly, the two reactions could be rendered in tandem, thereby providing an expeditious approach to this family of natural products.