(+)-elisabethadione | 433717-71-6

• 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: (+)-elisabethadione
• CAS: 433717-71-6
• 化学式: C₂₀H₂₈O₃
• 分子量: 316.441
• InChiKey: IRXCXTYZMLAQJV-KCQAQPDRSA-N

物化性质

• 沸点：
  435.6±45.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (+)-elisabethadione 在 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 丙酮 为溶剂， 反应 20.0h， 生成 (5S,8R)-5,6,7,8-tetrahydro-2,5-dimethyl-3-methylamino-8-[(S)-6-methylhept-5-en-2-yl]naphthalene-1,4-dione
  参考文献：
  名称：

  Synthetic and Isolation Studies Related to the Marine Natural Products (+)-Elisabethadione and (+)-Elisabethamine

  摘要：

  These studies were conducted to determine the discrepancies between the spectroscopic data of the isolated and synthetic samples of the marine natural product (+)-elisabethadione. Attempts at the re-isolation of (+)-elisabethadione from Pseudopterogorgia elisabethae were unsuccessful, but during these efforts, two related natural products of O-methylelisabethadione (8) and O-methyl-nor-elisabethadione (9) were discovered. The total syntheses of these new natural products were accomplished by using the combined C-H activation/Cope rearrangement as the key step and the previously synthesized elisabethadione was converted to O-methylelisabethadione. These studies confirmed that the synthetic sample of (+)-elisabthadione was assigned the correct structure. The considerable differences in the data between the synthetic and natural samples of (+)-elisabethadione lead to the conclusion that the structure of the natural material was either miss-assigned or the published spectral data were incorrect. During the course of these studies, questions arose about the assigned structure of another natural product, elisabethamine, which was proposed to be an aminohydroquinone. Attempts at the synthesis of this compound revealed that the aminohydroquinone structure was unstable in air as it was readily oxidized to the quinone.

  DOI：

  10.1021/jo0618167
• 作为产物：
  描述：

  (S)-4-((1S,4R)-1,2,3,4-tetrahydro-5,7,8-trimethoxy-1,6-dimethylnaphthalen-4-yl)pentan-1-ol 在 正丁基锂 、 ammonium cerium(IV) nitrate 、 对甲苯磺酸一水合物 、 pyridinium chlorochromate 、 乙硫醇 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 、 苯 为溶剂， 反应 8.67h， 生成 (+)-elisabethadione
  参考文献：
  名称：

  结合的C–H活化/对位重排是（+）-伊利沙伯乙二酮和（+）-对-苯醌天然产物指定结构总合成中的关键步骤

  摘要：

  描述了（+）-伊利沙伯二酮（3）和（+）-对-苯醌天然产物4的指定结构的对映选择性总合成。天然产物中三个关键立体中心的立体控制形成是通过结合的C–H活化/ Cope重排，通过四丙lin酸二铑Rh 2（R -DOSP）4催化的C–H功能化过程而完成的（ DOSP ＝（N-十二烷基苯磺酰基）脯氨酸盐）。

  DOI：

  10.1016/j.tet.2006.05.086

文献信息

• Erogorgiaene congeners and methods and intermediates useful in the preparation of same
  申请人：The Research Foundation of State University of New York

  公开号：US07700798B1

  公开（公告）日：2010-04-20

  Disclosed are compounds having the formula: wherein R21 is an alkyl, aryl, alkoxy, hydroxy, or amino group or a halogen atom; wherein R2 is hydrogen or an alkyl, aryl, alkoxy, or amino group; wherein R23 and R24 are independently selected from hydrogen, an alkyl, aryl, alkoxy, hydroxy, or amino group, and a halogen atom or wherein R23 and R24, taken together with the carbon atom to which they are bound, form a ring; wherein R25 is hydrogen, an alkyl, aryl, alkoxy, hydroxy, or O-silyl group or a halogen atom; wherein Z, taken together with the carbons to which it is bonded, forms a 5-12 membered ring; and wherein Y is an electron withdrawing group. These compounds can be used to prepare erogorgiaene congeners, such as erogorgiaene, pseudopterosin A, helioporin E, pseudopteroxazole, colombiasin A, elisapoterosin B, elisabethadione, p-benzoquinone natural products, ileabethin, sinulobtain B, sinulobtain C, and sinulobtain D.

  揭示了具有以下结构的化合物： 其中R21是烷基、芳基、烷氧基、羟基、氨基或卤素原子；其中R2是氢或烷基、芳基、烷氧基或氨基；其中R23和R24分别独立地选自氢、烷基、芳基、烷氧基、羟基、氨基和卤素原子，或者R23和R24与它们所连接的碳原子一起形成环；其中R25是氢、烷基、芳基、烷氧基、羟基、O-硅基或卤素原子；其中Z与其连接的碳原子一起形成一个5-12环；Y是一个电子吸引基团。这些化合物可用于制备erogorgiaene同系物，如erogorgiaene、pseudopterosin A、helioporin E、pseudopteroxazole、colombiasin A、elisapoterosin B、elisabethadione、p-苯醌天然产物、ileabethin、sinulobtain B、sinulobtain C和sinulobtain D。
• US7700798B1
  申请人：——

  公开号：US7700798B1

  公开（公告）日：2010-04-20
• Application of the combined C–H activation/Cope rearrangement as a key step in the total syntheses of the assigned structure of (+)-elisabethadione and a (+)-p-benzoquinone natural product
  作者：Huw M.L. Davies、Xing Dai

  DOI：10.1016/j.tet.2006.05.086

  日期：2006.11

  The enantioselective total syntheses of the assigned structure of (+)-elisabethadione (3) and the (+)-p-benzoquinone natural product 4 is described. The stereocontrolled formation of the three key stereocenters in the natural products is achieved in a single step through the combined C–H activation/Cope rearrangement, a C–H functionalization process catalyzed by the dirhodium tetraprolinate, Rh2(R-DOSP)4

  描述了（+）-伊利沙伯二酮（3）和（+）-对-苯醌天然产物4的指定结构的对映选择性总合成。天然产物中三个关键立体中心的立体控制形成是通过结合的C–H活化/ Cope重排，通过四丙lin酸二铑Rh 2（R -DOSP）4催化的C–H功能化过程而完成的（ DOSP ＝（N-十二烷基苯磺酰基）脯氨酸盐）。
• Synthetic and Isolation Studies Related to the Marine Natural Products (+)-Elisabethadione and (+)-Elisabethamine
  作者：Xing Dai、Zhongliang Wan、Russell G. Kerr、Huw M. L. Davies

  DOI：10.1021/jo0618167

  日期：2007.3.1

  These studies were conducted to determine the discrepancies between the spectroscopic data of the isolated and synthetic samples of the marine natural product (+)-elisabethadione. Attempts at the re-isolation of (+)-elisabethadione from Pseudopterogorgia elisabethae were unsuccessful, but during these efforts, two related natural products of O-methylelisabethadione (8) and O-methyl-nor-elisabethadione (9) were discovered. The total syntheses of these new natural products were accomplished by using the combined C-H activation/Cope rearrangement as the key step and the previously synthesized elisabethadione was converted to O-methylelisabethadione. These studies confirmed that the synthetic sample of (+)-elisabthadione was assigned the correct structure. The considerable differences in the data between the synthetic and natural samples of (+)-elisabethadione lead to the conclusion that the structure of the natural material was either miss-assigned or the published spectral data were incorrect. During the course of these studies, questions arose about the assigned structure of another natural product, elisabethamine, which was proposed to be an aminohydroquinone. Attempts at the synthesis of this compound revealed that the aminohydroquinone structure was unstable in air as it was readily oxidized to the quinone.