9-isopropyl-2,2,5-trimethylphenaleno<1,9-bc>furan-8(2H)-one | 57517-08-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 非那烯类
• 英文名称: 9-isopropyl-2,2,5-trimethylphenaleno<1,9-bc>furan-8(2H)-one
• 英文别名: salivlenone；salvelinone；salvilenone；2-Isopropyl-4,4,7-trimethyl-1H-phenaleno-<1,9-bc>furan-1-on；9-Isopropyl-2,2,5-trimethyl-8H-phenaleno<1.9-bc>furan-8-on；9-Isopropyl-2,2,5-trimethyl-8H-phenaleno(1.9-bc)furan-8-on；5,13,13-trimethyl-10-propan-2-yl-12-oxatetracyclo[6.5.2.04,15.011,14]pentadeca-1(14),2,4,6,8(15),10-hexaen-9-one
• CAS: 57517-08-5
• 化学式: C₂₀H₂₀O₂
• 分子量: 292.378
• InChiKey: WDBJFWOOWQREKA-UHFFFAOYSA-N

物化性质

• 沸点：
  455.4±45.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-isopropyl-2,2,5-trimethylphenaleno<1,9-bc>furan-8(2H)-one 生成 Acetic acid 9-isopropyl-2,2,5-trimethyl-2,5,6,7-tetrahydro-1-oxa-cyclopenta[cd]phenalen-8-yl ester
  参考文献：
  名称：

  Weeratunga, Gamini; Austrup, Mona; Rodrigo, Russell, Journal of the Chemical Society. Perkin transactions I, 1988, p. 3169 - 3174

  摘要：

  DOI：
• 作为产物：
  描述：

  1,3-二甲氧基-2-(1-甲基乙基)苯 在 正丁基锂 、 氢溴酸 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 生成 9-isopropyl-2,2,5-trimethylphenaleno<1,9-bc>furan-8(2H)-one
  参考文献：
  名称：

  Zheng, Guo-Chi; Kojima, Tsutomu; Kakisawa, Hiroshi, Heterocycles, 1988, vol. 27, # 6, p. 1341 - 1344

  摘要：

  DOI：

文献信息

• Synthesis of Salvilenone, a Diterpenoid Phenalenone of<i>Salvia miltiorrhiza</i>
  作者：Guo-Chi Zheng、Hiroshi Kakisawa

  DOI：10.1246/bcsj.62.1117

  日期：1989.4.15

  Salvilenone 1, a phenalenone diterpene isolated from the roots of Salvia miltiorrhiza Bunge, was synthesized in thirteen steps from resorcinol dimethyl ether. Dihydrophenalenol derivative 19, a key intermediate, was treated with aqueous hydrobromic acid to give salvilenone accompanied by the formation of a hydroxy diketone 20.

  从丹参（Salvia miltiorrhiza Bunge）根部分离出的酚烯酮二萜--沙维烯酮 1 是由间苯二酚二甲醚经 13 个步骤合成的。二氢苯亚酚衍生物 19 是一种关键的中间体，经氢溴酸水溶液处理后可得到沙维烯酮，同时形成羟基二酮 20。
• Total Synthesis of the Phenalenone Diterpene Salvilenone
  作者：Rick L. Danheiser、Anna L. Helgason

  DOI：10.1021/ja00100a009

  日期：1994.10

  The application of a photochemical aromatic annulation strategy in a highly efficient total synthesis of the phenalenone diterpene salvilenone is reported. The pivotal step in the synthesis involves the assembly of the key dihydrophenalene 29 in one step via an annulation involving the siloxyalkyne 28 and either diazo ketone 8 or 9. The synthesis of the alpha-benzosuberone 8 was achieved in three steps beginning with 2-methylcyclopentanone by a route featuring an ''aryne-enolate condensation'' reaction. The alternative aromatic annulation substrate, the beta-benzosuberone 9, was prepared in four steps by a route based on the regiocontrolled ring expansion of the alpha-methylenetetralin 27. The key aromatic annulation was then accomplished by irradiating a mixture of either diazo ketone 8 or 9 and 1.4 equiv of the siloxyalkyne 28 in 1,2-dichloroethane at 20-25 degrees C using a standard Rayonet photochemical reactor. The reaction mixture was next diluted with an equal volume of solvent and heated overnight at 80 degrees C to complete the annulation; concentration and chromatographic purification furnished the tricyclic phenol 29 as colorless crystals in 60-71% yield. Finally, annulation of the furan ring and oxidation required three steps and provided the phenalenone diterpene in good yield. The synthetic routes described herein provide access to salvilenone in only seven or eight steps (via the alpha- and beta-benzosuberone strategies, respectively), half the number of steps required using the classical linear substitution approach reported previously. These highly efficient syntheses demonstrate the ability of the photochemical aromatic annulation strategy to dramatically streamline the synthesis of polycyclic aromatic compounds.
• A diterpenoid phenalenone from Salvia miltiorrhiza
  作者：Takenori Kusumi、Takashi Ooi、Teruo Hayashi、Hiroshi Kakisawa

  DOI：10.1016/s0031-9422(00)83136-2

  日期：1985.1
• Cyclization reactions of the o-naphthoquinone diterpene aethiopinone. A revision of the structure of prionitin.
  作者：Maria J. Sexmero Cuadrado、Maria C. De la Torre、Long Ze Lin、Geoffrey A. Cordell、Benjamin Rodriguez、Aurea Perales

  DOI：10.1021/jo00043a034

  日期：1992.8
• ZHENG, GUO-CHI;KAKISAWA, HIROSHI, BULL. CHEM. SOC. JAP., 62,(1989) N, C. 1117-1122
  作者：ZHENG, GUO-CHI、KAKISAWA, HIROSHI

  DOI：——

  日期：——