(3R*,3aR*,7R*,7S*)-octahydro-3-(hydroxymethyl)-8,8-dimethyl-2-oxo-3a,7-ethano-3aH-indene-4-carboxylic acid | 78739-66-9

• 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: (3R*,3aR*,7R*,7S*)-octahydro-3-(hydroxymethyl)-8,8-dimethyl-2-oxo-3a,7-ethano-3aH-indene-4-carboxylic acid
• 英文别名: (+)-5(6)-dihydro-6-hydroxyterrecyclic acid A；(1S,2S,5S,6S,9S)-2-(hydroxymethyl)-11,11-dimethyl-3-oxotricyclo[4.3.2.01,5]undecane-9-carboxylic acid
• CAS: 78739-66-9；117557-25-2；132831-49-3；132831-50-6
• 化学式: C₁₅H₂₂O₄
• 分子量: 266.337
• InChiKey: DFQGNWLQBKGFOD-AIGMQPKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R*,3aR*,7R*,7S*)-octahydro-3-(hydroxymethyl)-8,8-dimethyl-2-oxo-3a,7-ethano-3aH-indene-4-carboxylic acid 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 0.33h， 以94%的产率得到土曲环酸 A
  参考文献：
  名称：

  Total synthesis of dl-quadrone

  摘要：

  DOI：

  10.1021/ja00404a026
• 作为产物：
  描述：

  (1R^*,6S^*,7S^*)-10,10-dimethyl-4-oxotricyclo<4.3.2.0^2,6>undec-2-en-7-carboxylic acid 在 palladium on activated charcoal 氢气 、 lithium diisopropyl amide 作用下， 以 甲醇 为溶剂， 反应 2.33h， 生成 (3R*,3aR*,7R*,7S*)-octahydro-3-(hydroxymethyl)-8,8-dimethyl-2-oxo-3a,7-ethano-3aH-indene-4-carboxylic acid
  参考文献：
  名称：

  Total synthesis of dl-quadrone

  摘要：

  DOI：

  10.1021/ja00404a026

文献信息

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

  DOI：10.1021/ja00404a026

  日期：1981.7