(+/-)-quadrone | 66550-08-1

• 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: (+/-)-quadrone
• 英文别名: dl-quadrone；(1S,2S,5R,9S,12S)-13,13-dimethyl-7-oxatetracyclo[7.5.0.01,5.02,12]tetradecane-4,8-dione
• CAS: 66550-08-1；74807-65-1；87480-01-1
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: BBIDMUQZCCGABN-UXSWQMMLSA-N

物化性质

• 熔点：
  183-184 °C
• 沸点：
  418.8±38.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)
• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  土曲环酸 A 反应 0.08h， 生成 (+/-)-quadrone
  参考文献：
  名称：

  Total synthesis of dl-quadrone

  摘要：

  DOI：

  10.1021/ja00532a049

文献信息

• Total synthesis of (.+-.)-quadrone
  作者：Steven D. Burke、Charles William Murtiashaw、Jeffrey O. Saunders、Jeffrey A. Oplinger、Meera S. Dike

  DOI：10.1021/ja00328a043

  日期：1984.8

  Synthese totale de la guadrone (±) a partir d'une spiro [4.5] decadienone par scission oxydante/addition Michael/cyclisation aldol. Toutes les reactions de formation des liaisons C−C sont intramoleculaires

  合成这些totale de la guadrone (±) a partir d'une spiro [4.5] decadienone par scission oxydante/addition Michael/cyclisation aldol。Toutes les 反应 deformation des liaisons C-C sont intramoleculaires
• Cytotoxic Constituents of <i>Aspergillus </i><i>t</i><i>erreus</i> from the Rhizosphere of <i>Opuntia </i><i>v</i><i>ersicolor</i> of the Sonoran Desert
  作者：E. M. Kithsiri Wijeratne、Thomas J. Turbyville、Zhongge Zhang、Donna Bigelow、Leland S. Pierson、Hans D. VanEtten、Luke Whitesell、Louise M. Canfield、A. A. Leslie Gunatilaka

  DOI：10.1021/np030266u

  日期：2003.12.1

  A novel cyclopentenedione, asterredione (1), two new terrecyclic acid A derivatives, (+)-5(6)-dihydro-6-methoxyterrecyclic acid A (2) and (+)-5(6)-dihydro-6-hydroxyterrecyclic acid A (3), and five known compounds, (+)-terrecyclic acid A (4), (-)-quadrone (5), betulinan A (6), asterriquinone D (7), and asterriquinone C-1 (8), were isolated from Aspergillus terreus occurring in the rhizosphere of Opuntia versicolor, using bioassay-guided fractionation. Acid-catalyzed reaction of 2 under mild conditions afforded 4, whereas under harsh conditions 2 yielded 5 and (-)-isoquadrone (9). Catalytic hydrogenation and methylation of 4 afforded 5(6)-dihydro-terrecyclic acid A (10) and (+)-terrecyclic acid A methyl ester (11), respectively. The structures of 1-11 were elucidated by spectroscopic methods. All compounds were evaluated for cytotoxicity in a panel of three sentinel cancer cell lines, NCI-H460 (non-small cell lung cancer), MCF-7 (breast cancer), and SF-268 (CNS glioma), and were found to be moderately active. Cell cycle analysis of 2, 4, and 5 using the NCI-H460 cell line indicated that 4 is capable of disrupting the cell cycle through an apparent arrest to progression at the G(1) and G(2)/M phases in this p53 competent cell line. A pathway for the biosynthetic origin of asterredione (1) from asterriquinone D (7) is proposed.
• Nakagawa, Masahira; Sakai, Heiichi; Isogai, Akira, Agricultural and Biological Chemistry, 1984, vol. 48, # 9, p. 2279 - 2284
  作者：Nakagawa, Masahira、Sakai, Heiichi、Isogai, Akira、Hirota, Akira

  DOI：——

  日期：——
• Synthetic studies directed at (±)-quadrone. A new end game.
  作者：Steven D. Burke、Charles William Murtiashaw、Jeffrey A. Oplinger

  DOI：10.1016/s0040-4039(00)88066-1

  日期：1983.1
• Total synthesis of dl-quadrone
  作者：Samuel Danishefsky、Kenward Vaughan、Robert Gadwood、Kazuo Tsuzuki

  DOI：10.1021/ja00404a026

  日期：1981.7