(-)-9-oxo-10-epi-α-cyperone | 90760-60-4

• 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: (-)-9-oxo-10-epi-α-cyperone
• 英文别名: 10-epieudesma-4,11-diene-3,9-dione；(3S,8aR)-5,8a-dimethyl-3-prop-1-en-2-yl-3,4,7,8-tetrahydro-2H-naphthalene-1,6-dione
• CAS: 90760-60-4
• 化学式: C₁₅H₂₀O₂
• 分子量: 232.323
• InChiKey: RHPIHUSALNVVCT-XHDPSFHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (-)-9-oxo-10-epi-α-cyperone 在 亚磷酸三苯酯 、 sodium tetrahydroborate 、 正丁基锂 、 三氟化硼乙醚 、 potassium carbonate 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 41.5h， 生成 (4aS,6R,8R,8aS)-4a,8-dihydroxy-4,8a-dimethyl-6-prop-1-en-2-yl-5,6,7,8-tetrahydro-1H-naphthalen-2-one
  参考文献：
  名称：

  An enantioselective synthetic strategy toward the polyhydroxylated agarofuran

  摘要：

  This paper describes a new approach for the enantioselective syntheses of naturally occurring polyhydroxylated dihydroagarofuran sesquiterpenoids starting from (-)-carvone. Through utilizing asymmetric Robinson annulation and acetoxylation as key steps, the agarofuran skeleton was enantioselectively constructed and an oxyfunctionalized group was introduced into the C-l position. The important intermediate 23 to dihydroagarofuran was obtained in eleven steps. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00377-x
• 作为产物：
  描述：

  hydroxycarvone 在 氢氧化钾 、 D-苯丙氨酸 、 D(+)-10-樟脑磺酸 作用下， 以 甲醇 为溶剂， 反应 150.0h， 生成 (-)-9-oxo-10-epi-α-cyperone
  参考文献：
  名称：

  An enantioselective synthetic strategy toward the polyhydroxylated agarofuran

  摘要：

  This paper describes a new approach for the enantioselective syntheses of naturally occurring polyhydroxylated dihydroagarofuran sesquiterpenoids starting from (-)-carvone. Through utilizing asymmetric Robinson annulation and acetoxylation as key steps, the agarofuran skeleton was enantioselectively constructed and an oxyfunctionalized group was introduced into the C-l position. The important intermediate 23 to dihydroagarofuran was obtained in eleven steps. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00377-x

文献信息

• Li, Yulin; Chen, Xin; Shao, Sichang, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 3, p. 356 - 357
  作者：Li, Yulin、Chen, Xin、Shao, Sichang、Li, Tongshuang

  DOI：——

  日期：——
• Studies on the Dehydrogenation of 9-Oxygenated-eudesma-4-en-3-ones with DDQ
  作者：Lijun Liu、Fajun Nan、Zhaoming Xiong、Tongshuang Li、Yulin Li

  DOI：10.1080/00397919608003648

  日期：1996.2

  9-Acetoxy-eudesma-4,11-dien-3-ones (4a, 4b) and 9-acetoxy-14-noreudesma-4,11-dien-3-ones (5a, 5b) were treated with DDQ in dioxane to yield normal 1,2-dehydro-products, whereas 14-noreudesma-4,11-dien-3,9-diones (2a, 2b) afforded a rearranged aromatic product, 1-hydroxy-15-noreudesma-1, 3, 5 (10), 11-tetraen-9-one (3). No reaction was observed by treatment of eudesma-4,11-dien-3,9-diones (1a, 1b) with DDQ under the same conditions. The effect of 10-methyl configuration on this reaction is also discussed.
• AGAMI, C.;MEYNIER, F.;PUCHOT, C.;GUILHEM, J.;PASCARD, C., TETRAHEDRON, 1984, 40, N 6, 1031-1038
  作者：AGAMI, C.、MEYNIER, F.、PUCHOT, C.、GUILHEM, J.、PASCARD, C.

  DOI：——

  日期：——
• An enantioselective synthetic strategy toward the polyhydroxylated agarofuran
  作者：Gang Zhou、Xiaolei Gao、Weidong Z Li、Yulin Li

  DOI：10.1016/s0040-4039(01)00377-x

  日期：2001.4

  This paper describes a new approach for the enantioselective syntheses of naturally occurring polyhydroxylated dihydroagarofuran sesquiterpenoids starting from (-)-carvone. Through utilizing asymmetric Robinson annulation and acetoxylation as key steps, the agarofuran skeleton was enantioselectively constructed and an oxyfunctionalized group was introduced into the C-l position. The important intermediate 23 to dihydroagarofuran was obtained in eleven steps. (C) 2001 Elsevier Science Ltd. All rights reserved.