大果桉醛C | 142628-53-3

• 物质功能分类: 天然产物 - 倍半萜
• 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
• 中文名称: 大果桉醛C
• 英文名称: macrocarpal C
• 英文别名: macrocarpal G；5-[(1R)-1-[(1aR,4aR,7S,7aR,7bR)-1,1,7-trimethyl-4-methylidene-1a,2,3,4a,5,6,7a,7b-octahydrocyclopropa[h]azulen-7-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde
• CAS: 142628-53-3
• 化学式: C₂₈H₃₈O₅
• 分子量: 454.607
• InChiKey: IEWHEHWXBLPFER-HUCVFKCKSA-N

物化性质

• 沸点：
  509.6±50.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  大果桉醛C 在 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 乙醇 、 乙腈 为溶剂， 生成 (+)-5-<(1'R)-1'-((1R,2R,4R,8R,11S)-3,3,11-trimethyl-7-methylenetricyclo<6.3.0.0^2,4>undec-11-yl)-3'-methylbutyl>-2,4,6-trimethoxybenzene-1,3-dimethanol
  参考文献：
  名称：

  Macrocarpals: HIV-RTase inhibitors of Eucalyptus globulus

  摘要：

  Five HIV-RTase inhibitors, macrocarpals A-E, have been isolated from Eucalyptus globulus. X-ray diffraction studies as well as spectral and chemical investigations established the structures 1, 2, 3, 12, and 13, respectively.

  DOI：

  10.1016/s0040-4039(00)79578-5
• 作为产物：
  描述：

  (-)-dimethyl 5-<(1'R)-1'-((1R,2R,4R,7S,8R,11S)-7-(hydroxymethyl)-3,3,11-trimethyltricyclo<6.3.0.0^2,4>undec-9-en-11-yl)-3'-methylbutyl>-2,4,6-trimethoxyisophthalate 在 palladium on activated charcoal 六甲基磷酰三胺 、 2-硝基苯基丝氰酸酯 、 四丙基高钌酸铵 、 三丁基膦 、 氢气 、 双氧水 、 二异丁基氢化铝 、 lithium p-toluenethiolate 、 N-甲基吗啉氧化物 作用下， 以 甲醇 、 甲苯 、 乙腈 为溶剂， -78.0~50.0 ℃ 、506.62 kPa 条件下， 生成 大果桉醛C
  参考文献：
  名称：

  First stereoselective total synthesis of macrocarpal C: structure elucidation of macrocarpal G

  摘要：

  首次实现了大果壳素C的立体选择性全合成，该合成通过硅醚二烯醇与新型六取代苯铬三羰基复合物（作为光学活性苄基阳离子等价物）的偶联反应完成，从而阐明了大果壳素C和大果壳素G的身份。

  DOI：

  10.1039/a705231f

文献信息

• Plants extracts for use in brain modulation
  申请人：InterMed Discovery GmbH

  公开号：EP1939166A1

  公开（公告）日：2008-07-02

  Compounds obtainable from plants, e.g. of the genus Eucalyptus, or from microorganisms are shown to be useful as CNS activity modulators useful e.g. in the treatment of depression, for lifting mood and/or for increasing behavioural initiative and the like. This use and related aspects form embodiments of the invention. Also compounds as such are presented. The compounds useful are acylphloroglucine derivatives of the formula I, wherein the substituents are as defined in the description.

  从植物（如桉树属）或微生物中提取的化合物可用作中枢神经系统活性调节剂，例如用于治疗抑郁症、改善情绪和/或提高行为主动性等。这种用途和相关方面构成了本发明的实施例。此外，还介绍了本发明的化合物。 有用的化合物是式 I 的酰基氯葡萄糖衍生物、 其中的取代基如描述中所定义。
• Total Synthesis of (−)-Macrocarpal C. Stereoselective Coupling Reaction with a Novel Hexasubstituted Benzene Cr(CO)₃ Complex as a Biomimetic Chiral Benzyl Cation Equivalent
  作者：Tetsuaki Tanaka、Hidenori Mikamiyama、Kimiya Maeda、Chuzo Iwata、Yasuko In、Toshimasa Ishida

  DOI：10.1021/jo981413+

  日期：1998.12.1

  The first total synthesis of (-)-macrocarpal C (3) is described. The synthesis features a highly stereoselective coupling reaction of silyldienol ether 6 with biomimetic benzyl cation species (R)- and (S)-B, which were generated from novel hexasubstituted benzene chromium tricarbonyl complexes (R)- and (S)-17. At the final step of the total synthesis, we developed the tris-O-demethylation of macrocarpal C trimethyl ether 34 under basic conditions using lithium p-thiocresolate. Moreover, spectroscopic evidence shows that the synthetic (-)-3 is identical to natural macrocarpal G (4).
• Semisynthesis of Macrocarpal C and Analogues by Selective Dehydration of Macrocarpal A or B
  作者：Julien Alliot、Edmond Gravel、Laurent Larquetoux、Marc Nicolas、Eric Doris

  DOI：10.1021/np400869z

  日期：2013.12.27

  Macrocarpals A and C are structurally related compounds that have been extracted from different Eucalyptus species. Although macrocarpal C is of biological interest, its isolation in pure form is difficult to achieve. We report herein an efficient method for the semisynthesis of macrocarpal C by selective exo-dehydration of another member of the macrocarpal family, macrocarpal A. We also report the semisynthesis of three new macrocarpal structures derived from either macrocarpal A or B.
• EUCALYPTUS EXTRACT, METHOD OF PREPARATION AND THERAPEUTIC USES THEREOF
  申请人：Fiorini-Puybaret Christel

  公开号：US20090324754A1

  公开（公告）日：2009-12-31

  The present invention relates to the use of a Eucalyptus for preparation of a drug or a dietary supplement intended for treatment and/or prevention of affections or pathologies caused by neuromediator recapture disorder. The present invention also relates to a new enriched extract of Eucalyptus characterized in that it contains at least one compound having the formula (I) or any one of its diastereoisomers in which R1 forms a C═CH2 substituent with the carbon to which it is joined, a formula (II) substituent and R2 which represents an isobutyl, α-isobutyl or β-isobutyl substituent; and the method of preparation thereof.
• PLANTS EXTRACTS FOR USE IN BRAIN MODULATION
  申请人：Roemer Ernst

  公开号：US20110021613A1

  公开（公告）日：2011-01-27

  Compounds obtainable from plants, e.g. of the genus Eucalyptus , or from microorganisms are shown to be useful as CNS activity modulators useful e.g. in the treatment of depression, for lifting mood and/or for increasing behavioural initiative and the like. This use and related aspects form embodiments of the invention. Also compounds as such are presented. The compounds useful are acylphloroglucine derivatives of the formula I, wherein the substituents are as defined in the description.