Royleanone | 6812-87-9

• 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: Royleanone
• 英文别名: (+/-)-royleanone；(+/-)-Royleanon
• CAS: 6812-87-9；37866-99-2
• 化学式: C₂₀H₂₈O₃
• 分子量: 316.441
• InChiKey: KZAPVZIQILABNM-ZUOKHONESA-N

物化性质

• 沸点：
  426.4±45.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  23.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (4bR,8aR)-1,3,4-trimethoxy-4b,8,8-trimethyl-2-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-9-ol 在 咪唑 、 偶氮二异丁腈 、 氧气 、 三正丁基氢锡 、 三溴化硼 、 sodium hydride 作用下， 生成 Royleanone
  参考文献：
  名称：

  A synthesis of the abietane diterpenoid quinone (±)-royleanone via maleoylcobalt technology.

  摘要：

  DOI：

  10.1016/s0040-4039(00)97454-9

文献信息

• The Total Synthesis of (±)-Royleanone
  作者：Yakudo Tachibana

  DOI：10.1246/bcsj.48.298

  日期：1975.1

  The total synthesis of (±)-royleanone (I) has been achieved. 5,7,8-Trimethoxy-1-tetralone (III) was converted into (±)-5,7,8-trimethoxy-1-methyl-2-tetralone (VII) via a dihydronaphthalene derivative (IV). The annelation of VII with methyl vinyl ketone gave a (±)-hexahydro-2-oxophenanthrene derivative (VIII), which was then further converted into (±)-11,12,14-trimethoxy-3-oxopodocarpa-5,8,11,13-tetraene

  (±)-royleanone (I) 的全合成已经实现。通过二氢萘衍生物 (IV) 将 5,7,8-三甲氧基-1-四氢萘酮 (III) 转化为 (±)-5,7,8-三甲氧基-1-甲基-2-四氢萘酮 (VII)。VII 与甲基乙烯基酮的退火得到 (±)-六氢-2-氧代菲衍生物 (VIII)，然后进一步转化为 (±)-11,12,14-三甲氧基-3-oxopodocarpa-5,8， 11,13-四烯(IX)。IX 在氧化铂上加氢得到两种二氢衍生物 (X) 和 (XI)，比例约为 1 : 7，A/B 环连接处的这些构型分别被鉴定为反式和顺式。因此，对IX进行硫缩酮化，然后进行脱硫，得到(±)-11,12,14-三甲氧基podocarpa-5,8,11,13-四烯(XV)。XV 在 10% 钯碳上加氢得到 (±)-11,12,14-trimethoxypodocarpa-8,11，13-三烯 (XII)
• Aromatic Annulation Strategy for the Synthesis of Angularly-Fused Diterpenoid Quinones. Total Synthesis of (+)-Neocryptotanshinone, (-)-Cryptotanshinone, Tanshinone IIA, and (.+-.)-Royleanone
  作者：Rick L. Danheiser、David S. Casebier、Fariborz Firooznia

  DOI：10.1021/jo00131a006

  日期：1995.12

  The application of a photochemical aromatic annulation strategy in highly efficient total syntheses of several diterpenoid quinones isolated from the traditional Chinese medicine Dan Shen is reported. The pivotal step in each synthesis involves the assembly of a key tricyclic intermediate via the application of a recently developed ''second-generation'' photochemical aromatic annulation method for the construction of highly substituted aromatic systems. In the total synthesis of neocrypto-tanshinone,;the synthesis of the requisite diazo ketone annulation substrate 7 was achieved using palladium-mediated coupling reactions and an intramolecular Friedel-Crafts cyclization to form key carbon-carbon bonds. The pivotal aromatic annulation reaction was then accomplished by irradiating a solution of the diazo ketone 7 and the readily available siloxyalkyne 6 in benzene at room temperature. The desired tricyclic phenol 16 was produced in 58-65% yield and was then converted to (+)-neocryptotanshinone (1) by treatment with tetra-n-butylammonium fluoride in the presence of oxygen. Cyclization to generate (-)-cryptotanshinone (2) was accomplished in high yield by brief exposure of 1 to an ethanolic solution of concentrated sulfuric acid, and dehydrogenation of 2 with DDQ furnished tanshinone IIA (3). As a further demonstration of the utility of the photochemical aromatic annulation strategy in the construction of angularly-fused diterpenes, the total synthesis of(+/-)-royleanone (4) was also investigated. Irradiation of a solution of the diazo ketone 18 and siloxyalkyne 25 produced the tricyclic intermediate 26, which was converted in two steps to royleanone by desilylation and oxidation.
• A synthesis of the abietane diterpenoid quinone (±)-royleanone via maleoylcobalt technology.
  作者：Lanny S. Liebeskind、Ramakrishnan Chidambaram、Sanjay Nimkar、Dennis Liotta

  DOI：10.1016/s0040-4039(00)97454-9

  日期：——