Isophoto-α-santoninlacton | 1618-98-0

• 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: Isophoto-α-santoninlacton
• 英文别名: isophotosantonin；Isophotosantoninlacton；(3S)-3abeta,4,5,6,6abeta,9balpha-Hexahydro-3,6,9-trimethyl-6beta-hydroxyazuleno[4,5-b]furan-2,8(3H,7H)-dione；(3S,3aS,6R,6aR,9bS)-6-hydroxy-3,6,9-trimethyl-3a,4,5,6a,7,9b-hexahydro-3H-azuleno[4,5-b]furan-2,8-dione
• CAS: 1618-98-0
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: FUKGETHUQZLZRJ-YIUCUBBLSA-N

物化性质

• 熔点：
  162.4-163.2 °C
• 沸点：
  474.4±45.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Isophoto-α-santoninlacton 在 吡啶 、 1-pentynyl copper 、 lithium aluminium tetrahydride 、 氯化亚砜 、 水 、 sodium acetate 、 铬酸 、 溶剂黄146 、 儿萘酚硼烷 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 反应 10.17h， 生成 (3aS)-3-甲基-5alpha-[(R)-1,5-二甲基-4-己烯基]-8-亚甲基-1,3aalpha,4,5,6,7,8,8abeta-八氢薁-4alpha-醇
  参考文献：
  名称：

  Highly stereoselective total syntheses of (+)-pachydictyol A and (-)-dictyolene, novel marine diterpenes from brown seaweeds of the family dictyotaceae

  摘要：

  DOI：

  10.1021/ja00536a036
• 作为产物：
  描述：

  山道年 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 7.0h， 以75%的产率得到Isophoto-α-santoninlacton
  参考文献：
  名称：

  11,13-脱氢癸二酸-瓜内醇化物的制备及植物毒性评价。

  摘要：

  使用一种涉及高产光化学反应的简便策略，由市售的α-桑顿宁（11）合成11,13-脱氢癸二酚内酯，一种特殊的倍半萜烯内酯。来自蒿的天然产物10和17以高产率合成。具体地，以五个步骤获得化合物10，总产率为17％。倍半萜内酯在黄化的小麦胚芽鞘生物测定中进行了测试，活性最高的化合物在标准目标物种上进行了测定。与已知的除草剂Logran相比，瓜亚胺内酯13具有最高的植物毒性活性。

  DOI：

  10.1021/acs.jnatprod.9b00285

文献信息

• Photochemische Reaktionen. 2. Mitteilung. Über gegenseitige Beziehungen und Umwandlungen bei Bestrahlungsprodukten des Santonins
  作者：D. Arigoni、H. Bosshard、H. Bruderer、G. Büchi、O. Jeger、L. J. Krebaum

  DOI：10.1002/hlca.19570400621

  日期：——

  Irradiation of santonin in dioxan solution or in alcohol yields a new isomer, lumisantonin, which in turn has been correlated with 3 known compounds: photosantonin, photosantonic acid and isophotosantonic acid lactone. The chemistry of lumisantonin is interpreted in terms of structure b.

  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。
• Barton et al., Journal of the Chemical Society, 1957, p. 929,934
  作者：Barton et al.

  DOI：——

  日期：——
• Synthetic Studies on Arglabin Diene; An Alleged Precursor to Arteminolides
  作者：Jeong-Hun Sohn

  DOI：10.5012/bkcs.2012.33.1.289

  日期：2012.1.20
• Facile Preparation of Bioactive<i>seco</i>-Guaianolides and Guaianolides from<i>Artemisia gorgonum</i>and Evaluation of Their Phytotoxicity
  作者：Francisco A. Macías、Alejandro Santana、Azusa Yamahata、Rosa M. Varela、Frank R. Fronczek、José M. G. Molinillo

  DOI：10.1021/np300639b

  日期：2012.11.26

  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.
• Ultrasound assisted reductive cleavage of eudesmane and guaiane γ-enonelactones. Synthesis of 1α,7α,10αH-guaian-4,11-dien-3-one and hydrocolorenone from santonin
  作者：Gonzalo Blay、Victoria Bargues、Luz Cardona、Begoña Garcı́a、José R Pedro

  DOI：10.1016/s0040-4020(01)00986-3

  日期：2001.11

  Ultrasound enhances the rate of reductive cleavage of the C-6-oxygen bond of sesquiterpene enonelactones. trans-Eudesmanolides 1c-1g, cis-eudesmanolides 2a-2c, and trans-guaianolides 4a-4d react with Zn in acetic acid-H2O under sonochemical conditions to afford the corresponding sesquiterpene. acids 3a-3g and 5a-5d, respectively in good yields. Starting from 5d two natural guaianes 1 alpha ,7 alpha ,10 alphaH-guaian-4, 11-dien-3-one (6) and hydrocolorenone (7) have been prepared in good yields through a straightforward sequence. (C) 2001 Elsevier Science Ltd. All rights reserved.