(+)-7-epi-α-cyperone | 547-26-2

• 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: (+)-7-epi-α-cyperone
• 英文别名: (4aS,7S)-1,4a-dimethyl-7-(prop-1-en-2-yl)-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one；(+)-6-Epi-α-cyperone；7βH-eudesma-4,11-dien-3-one；7βH-Eudesma-4,11-dien-3-on；(+)-Epi-α-Cyperon；(4aS,7S)-1,4a-dimethyl-7-prop-1-en-2-yl-3,4,5,6,7,8-hexahydronaphthalen-2-one
• CAS: 547-26-2
• 化学式: C₁₅H₂₂O
• 分子量: 218.339
• InChiKey: KUFXJZXMWHNCEH-WFASDCNBSA-N

物化性质

• 沸点：
  80-81 °C(Press: 0.01 Torr)
• 密度：
  0.97±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+)-7-epi-α-cyperone 在 硫酸 作用下， 生成 β-cyperone
  参考文献：
  名称：

  倍半萜类化合物-IV：氰化物离子与eudesmane系列中的某些共轭酮的反应

  摘要：

  氰化物离子与（+）-7β（H）-eudesm-4,11-dien-3-one（II），（+）-eudesm-4,11-dien-3-one（XI）和讨论了（+​​）-eudesm-4,6-dien-3-one（XVI）。

  DOI：

  10.1016/0040-4020(65)80011-4
• 作为产物：
  描述：

  ent-5-hydroxy-10α-eudesm-11-en-3-one 在 盐酸 作用下， 以 乙醇 为溶剂， 以82%的产率得到(+)-7-epi-α-cyperone
  参考文献：
  名称：

  Enantioselective Total Syntheses of (−)-7βH-Eudesmane-4α,11-diol and (+)-ent-7βH-Eudesmane-4α,11-diol

  摘要：

  The syntheses of (-)-7 beta H-eudesmane-4 alpha,11-diol (2) and (+)-ent-7 beta H-eudesmane-4 alpha,11-diol (ent-2) were carried out starting from (-)- and (+)-dihydrocarvones. As a result, the structure, including absolute configuration, of the naturally occurring eudesmane-4,11-diol isolated from Pluchea arguta was determined to be (+)-ent-7 beta H-eudesmane-4 alpha,11-diol (ent-2).

  DOI：

  10.1021/np9702906

文献信息

• The synthesis of chiral decalones, (−)-1,1,4a-trimethyl-2-decalol and (+)-geosmin from S-(+)-carvone (part 3)
  作者：Henk J. Swarts、Anja A. Haaksman、Ben J.M. Jansen、Aede de Groot

  DOI：10.1016/s0040-4020(01)88303-4

  日期：1992.1

  The cholesterol biosynthesis inhibitor (−),1,1,4a-trimethyl-2-decalol (4), the chiral decalones 6 and 7, and (+)-geosmin (9 were synthesized from S-(+)-carvone. Annelation of S-(−)-dihydrocarvone followed by methylation gave compound 8 which was used as a key intermediate for the synthesis of decalol 4 and ketone 5. A short isomerisation-ozonation sequence was developed for the removal of the isopropenyl

  由S-（+）-香芹酮合成胆固醇生物合成抑制剂（-），1,1,4a-三甲基-2-癸醛（4），手性十碳六烯酮6和7和（+）-土臭素（9）。 （ - - ） - S的dihydrocarvone接着进行甲基化，得到化合物8，其被用作关键中间体用于合成decalol 4和酮5。短异构臭氧化序列被用于除去异丙烯基的开发酮6和（十）十足动物（9）通过羰基转座从十全十（5）中获得7个。（+）-geosmin（9使用Criegee重排除去异丙烯基而合成）。
• Anionic Polycyclization Entry to Tricycles Related to Quassinoids and Terpenoids: A Stereocontrolled Total Synthesis of (+)-Cassaine
  作者：Kontham Ravindar、Pierre-Yves Caron、Pierre Deslongchamps

  DOI：10.1021/jo501122k

  日期：2014.9.5

  A full account of our anionic polycyclization approach to access highly functionalized tricycles related to quassinoids and terpenoids from several optically active bicyclic enone systems and Nazarov reagents is presented. (+)-Carvone is the only chiral source used to fix the entire stereochemistry of all of the tricycles, and the stereochemical outcome of this process was unambiguously determined

  完整介绍了我们的阴离子多环化方法，可从多个旋光性双环烯酮系统和Nazarov试剂中获得与类quassinoids和萜类化合物有关的高度官能化的三环化合物。（+）-香芹酮是用于固定所有三轮车的整个立体化学的唯一手性来源，该过程的立体化学结果通过X射线晶体学分析明确确定。该策略的效用通过与高度有效的抗癌天然产物Bruceantin（类quassinoid家族的成员）有关的高级三轮车的立体控制结构，以及心钠素（+）-胱氨酸（Na +的非甾体抑制剂）的总合成得到了证明。-K + -ATPase。
• Stereoselectivity in microbiological transformation of stereoisomers of .ALPHA.- cyperone and dihydro-.ALPHA.-cyperone with Colletotrichum phomoides.
  作者：HIROSHI HIKINO、CHOHACHI KONNO、YAYOI IKEDA、NOBUKO IZUMI、TSUNEMATSU TAKEMOTO

  DOI：10.1248/cpb.23.1231

  日期：——

  Incubation of three stereoisomers of α-cyperone (1, 2, and 3) with Colletotrichum phomoides resulted in two types of modification hydroxylation (C-2 and C-6) in one isomer (2) and dehydrogenation (C-6 : C-7) in another isomer (3) at the nuclei and in three types of modification (hydration to an alcohol, allylic hydroxylation to an allyl alcohol, and oxidation to a 1, 2-glycol) at the side chains in all the isomers in different rates. On fermentation with the same microbe of three stereoisomers of dihydro-α-cyperone (16, 17, and 18), prepared for prevention of the side chain modification, hydroxylation at the nucleus (C-1) occurred merely in one isomer (16), and the same types of oxidation at the side chains also took place in all the isomers as in their congeners (1-3). The stereoselectivity and the probable mechanisms of the transformations are discussed.

  将三种立体异构体α-赛普酮（1、2和3）与Colletotrichum phomoides共培养后，在其中一种异构体（2）中发生了两种类型的修改羟基化（C-2和C-6），而在另一种异构体（3）中发生了去氢反应（C-6 : C-7），在所有异构体的侧链中以不同速率发生了三种类型的修改（转化为醇、烯丙羟基化为烯丙醇，以及氧化为1, 2-甘醇）。在与同一微生物共同发酵三种双氢α-赛普酮的立体异构体（16、17和18）时，为了防止侧链修改，羟基化仅在一种异构体（16）的核部位（C-1）发生，而在所有异构体的侧链中也发生了与其同源物（1-3）相同类型的氧化反应。讨论了转化的立体选择性和可能的机制。
• Sesquiterpenoids—I
  作者：D.W. Theobald

  DOI：10.1016/0040-4020(63)85042-5

  日期：1963.1

  The chemistry of some derivatives of (+)-6β-hrcroxy-7β(H)-eudesma-4,11-dien-3-one (IV) is described. In particular, the stereochemistry of the reduction products of (+)-7β(H)-eudesma-4,11-dien-3-6-dione (IX) with zinc in acetic acid is established. The 6β-configuration for the hydroxyl group in the ketone (IV) is confirmed by a chemical method.

  描述了（+）-6β-hrcroxy-7β（H）-eudesma-4,11-dien-3-one（IV）的某些衍生物的化学性质。特别地，建立了在乙酸中的（+）-7β（H）-eudesma-4,11-dien-3-6-dione（IX）与锌的还原产物的立体化学。通过化学方法确认了酮（IV）中的羟基的6β-构型。
• The structure of a new sesquiterpene isolated from tobacco
  作者：D.L. Roberts

  DOI：10.1016/s0031-9422(00)90175-4

  日期：1972.6

  Abstract A new eudesmane-type sesquiterpene, 1-keto-α-cyperone (I), has been isolated from domestic tobaccos. The structure and stereochemistry of I have been elucidated from spectroscopic data and from the chemical degradation of I to (+)α-cyperone (IV).

  摘要 从国产烟草中分离到了一种新的eudesmane 型倍半萜烯，1-keto-α-cyperone (I)。I 的结构和立体化学已从光谱数据和 I 向 (+)α-环萜酮 (IV) 的化学降解中阐明。