(1R,3aR,4R,7R)-1,2,3,3a,4,5,6,7-八氢-1,4-二甲基-7-(1-甲基乙烯基)-薁 | 22567-17-5

• 物质功能分类: 生物 - 生化试剂盒
• 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: (1R,3aR,4R,7R)-1,2,3,3a,4,5,6,7-八氢-1,4-二甲基-7-(1-甲基乙烯基)-薁
• 中文别名: (十)-γ-古芸烯
• 英文名称: γ-gurjunene
• 英文别名: (+)-γ-Gurjunen；γ-gurjenene；1,4-Dimethyl-7-(1-methylethenyl)-octahydroazulene；(1R,3aR,4R,7R)-1,4-dimethyl-7-prop-1-en-2-yl-1,2,3,3a,4,5,6,7-octahydroazulene
• CAS: 22567-17-5
• 化学式: C₁₅H₂₄
• 分子量: 204.356
• InChiKey: DUYRYUZIBGFLDD-AAVRWANBSA-N

物化性质

• 沸点：
  264-266 °C(lit.)
• 密度：
  0.918 g/mL at 20 °C(lit.)
• 闪点：
  110 °C
• LogP：
  6.895 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• WGK Germany：
  3
• 海关编码：
  2902909090
• 安全说明：
  S23,S24/25

反应信息

• 作为反应物：
  描述：

  (1R,3aR,4R,7R)-1,2,3,3a,4,5,6,7-八氢-1,4-二甲基-7-(1-甲基乙烯基)-薁 在 氯氟磺酰 作用下， 以 二氯甲烷 为溶剂， 以33%的产率得到(6R,10R)-3-Isopropyl-6,10-dimethyltricyclo[5.3.0]deca-2,7(1)-diene
  参考文献：
  名称：

  Polovinka; Shal'ko; Korchagina, Russian Journal of Organic Chemistry, 2000, vol. 36, # 1, p. 40 - 54

  摘要：

  DOI：
• 作为产物：
  描述：

  isoledene 以80%的产率得到(1R,3aR,4R,7R)-1,2,3,3a,4,5,6,7-八氢-1,4-二甲基-7-(1-甲基乙烯基)-薁
  参考文献：
  名称：

  Rienaecker, Roland; Graefe, Juergen, Angewandte Chemie, 1985, vol. 97, # 4, p. 348 - 349

  摘要：

  DOI：

文献信息

• Hydroxylation of sesquiterpenes by enzymes from chicory (Cichorium intybus L.) roots
  作者：Jan-Willem de Kraker、Marloes Schurink、Maurice C.R Franssen、Wilfried A König、Aede de Groot、Harro J Bouwmeester

  DOI：10.1016/s0040-4020(02)01479-5

  日期：2003.1

  A microsomal enzyme preparation of chicory roots catalyses the hydroxylation of various sesquiterpene olefins in the presence of NADPH. Most of these hydroxylations take place at an isopropenyl or isopropylidene group. The number of products obtained from any of the substrates is confined to one or, in a few cases, two sesquiterpene alcohols. In addition, the conversion of (+)-valencene into nootkatone

  菊苣根的微粒体酶制剂在NADPH存在下催化各种倍半萜烯的羟基化反应。这些羟基化大多数发生在异丙烯基或异亚丙基上。从任何底物获得的产物的数量限制为一种，或者在少数情况下为两种倍半萜烯醇。另外，观察到了（+）-瓦伦烯通过β-Nootkatol转化为Nootkatone。讨论了（+​​）-germacrene A羟化酶（一种细胞色素P450酶）和倍半萜内酯生物合成的其他酶在这些反应中的参与。
• First Synthesis, Confirmation of Stereochemistry, and Cytotoxic Activity of Oxyfungiformin
  作者：Marie Pascaline Rahelivao、Ingmar Bauer、Tilo Lübken、Olga Kataeva、Anne Vehlow、Nils Cordes、Hans‐Joachim Knölker

  DOI：10.1002/ejoc.202200809

  日期：2022.9.27

  chiral precursor guaiol. The absolute configuration of oxyfungiformin was established by a combination of X-ray analysis and comparison of the values for specific optical rotation. Oxyfungiformin and a diastereoisomer showed cytotoxic activity in a panel of human cancer cell models.

  以从手性前体愈创木酚开始的简明合成序列获得海洋倍半萜类氧化真菌菌素。通过 X 射线分析和比旋光度值的比较相结合，确定了 oxyfungiformin 的绝对构型。Oxyfungiformin 和一种非对映异构体在一组人类癌细胞模型中显示出细胞毒活性。
• Chemical study of the essential oil of Cyperus rotundus
  作者：Mesmin Mekem Sonwa、Wilfried A König

  DOI：10.1016/s0031-9422(01)00301-6

  日期：2001.11

  Minor constituents of the essential oil of Cyperus rotundus have been investigated. The three new sesquiterpene hydrocarbons (-)-isorotundene, (-)-cypera-2,4(15)-diene, (-)-norrotundene and the ketone (+)-cyperadione were isolated and their structures elucidated. The absolute configuration of (-)-rotundene was derived by chemical correlation and enantioselective gas chromatography.

  已经研究了香附精油的微量成分。分离出三种新的倍半萜烃 (-)-isorotundene、(-)-cypera-2,4(15)-diene、(-)-norrotundene 和酮 (+)-cyperradione，并阐明了它们的结构。(-)-rotundene 的绝对构型是通过化学关联和对映选择性气相色谱法得出的。
• 10.1016/s0031-9422(98)00170-8
  作者：Miyazawa, Mitsuo、Honjo, Yoshihiro、Kameoka, Hiromu

  DOI：10.1016/s0031-9422(98)00170-8

  日期：——

  Abstract The biotransformation of a sesquitepenod which possesses a guaiane skeleton, (+)- γ -gurjunene has been investigated using the plant pathogenic fungus, Glomerella cingulata as a biocatalyst. (+)- γ -Gurjunene was oxidized at the double bond of the isopropenyl group to (1 S ,4 S ,7 R ,10 R )-5-guaien-11,13-diol and in addition oxidized at the C–10 position to (1 S ,4 S ,7 R ,10 S )-5-guaien-10

  摘要 已经使用植物病原真菌 Glomerella cingulata 作为生物催化剂研究了具有愈创木酚骨架 (+)-γ-gurjunene 的倍半萜烯的生物转化。(+)- γ -Gurjunene 在异丙烯基的双键处被氧化为 (1 S ,4 S ,7 R ,10 R )-5-guaien-11,13-diol 并在 C-10 (1 S ,4 S ,7 R ,10 S )-5-guaien-10,11,13-triol 的位置。代谢产物的结构已根据其光谱数据阐明。
• Syntheses of Sesquiterpene Epoxides and Alcohols from γ-Gurjunene
  作者：Isabelle Bombarda、Emile M. Gaydou、Robert Faure、Jacqueline Smadja

  DOI：10.1021/jf960335t

  日期：1997.1.1

  gamma-Gurjunene, a natural sesquiterpene isolated from gurjun balsam, is obtained by isomerization of alpha-gurjunene in acidic medium. Oxidation of gamma-gurjunene by reaction with m-chloroperbenzoic acid yielded a mixture of two monoepoxides and two diepoxides. Reduction reaction of a mixture of diepoxides with 4 equiv of lithium aluminum hydride or lithium triethylborohydride allowed isolation of a single diol in 93% yield. Four diols were obtained when reduction was realized with 2 equiv of reducing agent, including an epoxy alcohol, two enediols, and a dienol. The structure formulas of the compounds were determinated using one- and two-dimensional NMR and gas chromatography-mass spectrometry.