1-oxomiltirone | 142546-16-5

• 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: 1-oxomiltirone
• 英文别名: 8,8-dimethyl-2-propan-2-yl-6,7-dihydrophenanthrene-3,4,5-trione
• CAS: 142546-16-5
• 化学式: C₁₉H₂₀O₃
• 分子量: 296.366
• InChiKey: VPIMKJVQYOXHSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  51.2
• 氢给体数：
  0
• 氢受体数：
  3

制备方法与用途

2-异丙基-8,8-二甲基-7,8-二氢菲-3,4,5(6H)-三酮是一种具有抗炎活性的C20-去甲双丁烷二萜，可以从鼠尾草叶中分离得到。

反应信息

• 作为反应物：
  描述：

  1-oxomiltirone 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以40%的产率得到
  参考文献：
  名称：

  Semisynthesis of miltirone, 1,2-dehydromiltirone, saligerone from carnosic acid and cytotoxities of their derivatives

  摘要：

  Miltirone, 1,2-dehydromiltirone, saligerone have been synthesized form carnosic acid. Among them, one step transformation of carnosic acid into miltirone was realized when decarboxylation/aromatization was promoted by Lewis acid. Moreover, 4 derivatives exhibited potent cytotoxic activities against three human cancer lines in vitro. (C) 2018 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2018.05.073
• 作为产物：
  描述：

  鼠尾草酸 在 aluminum oxide 、 N-溴代丁二酰亚胺(NBS) 、 三氟甲磺酸三甲基硅酯 、 戴斯-马丁氧化剂 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 、 水 为溶剂， 反应 29.0h， 生成 1-oxomiltirone
  参考文献：
  名称：

  Semisynthesis of miltirone, 1,2-dehydromiltirone, saligerone from carnosic acid and cytotoxities of their derivatives

  摘要：

  Miltirone, 1,2-dehydromiltirone, saligerone have been synthesized form carnosic acid. Among them, one step transformation of carnosic acid into miltirone was realized when decarboxylation/aromatization was promoted by Lewis acid. Moreover, 4 derivatives exhibited potent cytotoxic activities against three human cancer lines in vitro. (C) 2018 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2018.05.073

文献信息

• Total Synthesis of 1-Oxomiltirone and Arucadiol
  作者：Chang Ho Oh、Chaehyeon Seong、Juyeon Kang、Uiseong Chai、Dinh Hung Mac

  DOI：10.1055/s-0039-1690743

  日期：2020.12

  A practical and efficient approach for the total synthesis of arucadiol and 1-oxomiltirone is reported. The key step which involves an intramolecular [4+2] cycloaddition catalyzed by gold(III) bromide or copper(II) triflate leads to the formation of 6-6-6-fused aromatic abietane core.

  报道了一种合成arucadiol和1-oxomiltirone的实用高效方法。其中关键步骤涉及由金(III)溴化物或铜(II)三氟乙酸盐催化的分子内[4+2]环加成，导致形成6-6-6融合芳香松节烷核。
• Compounds from invasive Salvinias and methods of using the same
  申请人：STEPHEN F. AUSTIN STATE UNIVERSITY

  公开号：US10464963B2

  公开（公告）日：2019-11-05

  In some embodiments, the compositions and methods relate to compounds isolated from plants in the Salviniaceae family, pharmaceutical compositions comprising the same, and methods of using the same.

  在某些实施方案中，组合物和方法涉及从沙棘科植物中分离的化合物、包含这些化合物的药物组合物以及使用这些化合物的方法。
• Diterpenes from Salvia mellifera and their biogenetic significance
  作者：Antonio G González、Lucia S Andrés、Zahira E Aguiar、Javier G Luis

  DOI：10.1016/0031-9422(92)80282-j

  日期：1992.4

  The new diterpenes, 11,12-dihydroxy-20-nor-abieta-5(10),8,11,13-tetraen-1-one and isogaldosol, together with the known compounds carnosic acid, carnosol, rosmanol, rosmadial, galdosol and isorosmanol were isolated from the aerial part of Salvia mellifera. The structures of the new diterpenes were established from their spectral data and by chemical correlations. The co-occurrence of all these compounds in one species taken together with their chemical behaviour led to the postulation of a biogenetic pathway to highly oxidized abietatriene diterpenes in which enzymatic dehydrogenation processes and the participation of singlet-state oxygen appear to play an important role.
• COMPOUNDS FROM INVASIVE SALVINIAS AND METHODS OF USING THE SAME
  申请人：STEPHEN F. AUSTIN UNIVERSITY

  公开号：US20160002279A1

  公开（公告）日：2016-01-07

  In some embodiments, the compositions and methods relate to compounds isolated from plants in the Salviniaceae family, pharmaceutical compositions comprising the same, and methods of using the same.
• US9809615B2
  申请人：——

  公开号：US9809615B2

  公开（公告）日：2017-11-07