photosantanoic acid | 7712-40-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: photosantanoic acid
• 英文别名: 'Konjugiertes' Anhydro-isophoto-α-santonin-lacton；3-oxo-11β(S)H-4,10(1)-guaiadien-6α(S),12-olide；(11S)-6α-hydroxy-3-oxo-guaia-1(10),4-dien-12-oic acid-lactone；(11S)-6α-Hydroxy-3-oxo-guaja-1(10),4-dien-12-saeure-lacton；(3S,3aS,9bS)-3,6,9-trimethyl-3,3a,4,5,7,9b-hexahydroazuleno[4,5-b]furan-2,8-dione
• CAS: 7712-40-5
• 化学式: C₁₅H₁₈O₃
• 分子量: 246.306
• InChiKey: UWQOILVQKMPJDQ-BXGCZWRVSA-N

物化性质

• 熔点：
  97.5-98.5 °C
• 沸点：
  461.4±44.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  photosantanoic acid 在 臭氧 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以51%的产率得到4-methyl-5-[(2S,3S,4S)-4-methyl-5-oxo-3-(3-oxobutyl)-tetrahydrofuran-2-yl]-cyclopent-4-ene-1,3-dione
  参考文献：
  名称：

  Facile Preparation of Bioactiveseco-Guaianolides and Guaianolides fromArtemisia gorgonumand Evaluation of Their Phytotoxicity

  摘要：

  Commercially available santonin was used to synthesize seven sesquiterpene lactones using a fade strategy that involved a high-yielding photochemical reaction. Three natural products from Artemisia gorgonum were synthesized in good yields, and in the case of two compounds, absolute configurations were determined from X-ray quality crystals. The structures previously reported for these compounds were revised. Sesquiterpene lactones were tested using the etiolated wheat coleoptile bioassay, and the most active compounds were assayed in standard target species, seco-Guaianolide (4) showed higher phytotoxic activities than the known herbicide Logran. This high activity could be due to the presence of a cyclopentenedione ring. These results suggest that compound 4 should be involved in defense of A. gorgorum, displaying a wide range of activities that allow proposing them as new leads for development of a natural herbicide model with a seco-guaianolide skeleton.

  DOI：

  10.1021/np300639b
• 作为产物：
  描述：

  山道年 在 乙醇 、 硫酸 、 水 作用下， 生成 photosantanoic acid
  参考文献：
  名称：

  光化学反应。第二次沟通。关于降钙素辐照产品中的相互关系和转变

  摘要：

  在二恶烷溶液或酒精中辐照桑托宁会产生新的异构体，发光素，反过来又与3种已知化合物有关：光黄素，光子酸和异光子酸内酯。发光素的化学解释为结构b。

  DOI：

  10.1002/hlca.19570400621

文献信息

• The Photoarrangement of α-Santonin is a Single-Crystal-to-Single-Crystal Reaction:  A Long Kept Secret in Solid-State Organic Chemistry Revealed
  作者：Arunkumar Natarajan、C. K. Tsai、Saeed I. Khan、Patrick McCarren、K. N. Houk、Miguel A. Garcia-Garibay

  DOI：10.1021/ja073189o

  日期：2007.8.1

  formulated in the United States. Not surprisingly, while its photochemical behavior in solution has been relatively well-established, its solid-state photoreactivity has not been thoroughly characterized. In this communication, with a combination of polarizing microscopy, single-crystal X-ray diffraction, spectroscopic methods, chemical trapping, and product analyses, we have confirmed a remarkable

  α-Santonin 1 是一种具有重要历史意义的天然倍半萜内酯。它的固态光化学不仅是有记载的最古老的有机化合物，而且还是第一种在美国配制的药物。毫不奇怪，虽然它在溶液中的光化学行为已经相对完善，但它的固态光反应性还没有得到彻底的表征。在这次交流中，结合偏光显微镜、单晶 X 射线衍射、光谱方法、化学捕获和产品分析，我们确认了一系列非凡的事件，其中包括三个连续的固态反应。
• Iso-<i>seco</i>-tanapartholides: Isolation, Synthesis and Biological Evaluation
  作者：Edward F. Makiyi、Raquel F. M. Frade、Tomas Lebl、Ellis G. Jaffray、Susan E. Cobb、Alan L. Harvey、Alexandra M. Z. Slawin、Ronald T. Hay、Nicholas J. Westwood

  DOI：10.1002/ejoc.200901016

  日期：2009.11

  The isolation, identification and total synthesis of two plant-derived inhibitors of the NF-kappaB signaling pathway from the iso-seco-tanapartholide family of natural products is described. A key step in the efficient reaction sequence is a late-stage oxidative cleavage reaction that was carried out in the absence of protecting groups to give the natural products directly. A detailed comparison of

  描述了天然产物iso-seco-tanapartholide家族中两种植物来源的NF-kappaB信号通路抑制剂的分离，鉴定和总合成。有效反应顺序中的关键步骤是后期的氧化裂解反应，该反应在不存在保护基的情况下进行，直接得到天然产物。合成材料与天然产物样品的详细比较证明是有益的。对合成材料的生物学研究证实，这些化合物在NF-κB信号传导途径中起着晚期作用。（（c）Wiley-VCH Verlag GmbH＆Co.KGaA，69451 Weinheim，德国，2009年）。
• Guaianolides from Tanacetum annuum
  作者：Alejandro F. Barrero、Juan F. Sánchez、José Molina、Antonio Barrón、M del Mar Salas

  DOI：10.1016/0031-9422(90)85279-o

  日期：1990.1

  Abstract Five new guaianolides, in addition to four known guaianolides, have been isolated from extracts of the flowers of Tanacetum annuum . Structures and stereochemistries were elucidated from spectral data and chemically confirmed by correlations with α-santonin and mutual interconversions. Conformational and configurational analysis performed through the molecular mechanics calculations corroborate

  摘要 除了四种已知的愈创木酚内酯外，还从紫荆花的提取物中分离出了五种新的愈创木酚内酯。从光谱数据中阐明了结构和立体化学，并通过与 α-santonin 的相关性和相互转化进行了化学确认。通过分子力学计算进行的构象和构型分析证实了通过 JH 、H 值和 NOEDIF 实验获得的那些。获得了脱水内酯可能是人工制品的证据。
• Barton et al., Journal of the Chemical Society, 1957, p. 929,934
  作者：Barton et al.

  DOI：——

  日期：——
• Satoda et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1959, vol. 79, p. 267
  作者：Satoda et al.

  DOI：——

  日期：——