2-[(3S,3aS,5R,8S,8aS)-3,8-dimethylhexahydro-1H,4H-3a,8a-epoxyazulen-5-yl]propan-2-ol | 887627-91-0

• 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: 2-[(3S,3aS,5R,8S,8aS)-3,8-dimethylhexahydro-1H,4H-3a,8a-epoxyazulen-5-yl]propan-2-ol
• 英文别名: (1β,4αH,5β,7αH,10αH)-1,5-epoxyguaian-11-ol；[(3aS)-3a,8a-epoxy-3c,8c-dimethyl-(3ar,8ac)-decahydro-azulen-5c-yl)]-propan-2-ol；2-[(1S,3R,6S,7S,10S)-6,10-dimethyl-11-oxatricyclo[5.3.1.01,7]undecan-3-yl]propan-2-ol
• CAS: 887627-91-0
• 化学式: C₁₅H₂₆O₂
• 分子量: 238.37
• InChiKey: ZLTJNMGRSFNNFA-QIRZIZBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[(3S,3aS,5R,8S,8aS)-3,8-dimethylhexahydro-1H,4H-3a,8a-epoxyazulen-5-yl]propan-2-ol 在 吡啶 、 3,5-二甲基吡唑 、 chromium(VI) oxide 、 叔丁基过氧化氢 、 selenium(IV) oxide 、 aluminum (III) chloride 、 lithium aluminium tetrahydride 、 氯化亚砜 、 cerium(III) chloride heptahydrate 、 sodium methylate 、 四丁基碘化铵 、 sodium hydride 、 戴斯-马丁氧化剂 、 对甲苯磺酸 、 potassium hydroxide 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 癸烷 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 、 苯 为溶剂， 反应 72.67h， 生成 (4S,5R,8S,8aS)-4-hydroxy-3,3',3',8-tetramethyl-6,7,8,8a-tetrahydro-1H-spiro[azulene-5,2'-oxiran]-2(4H)-one
  参考文献：
  名称：

  Synthesis of Guaia-4(5)-en-11-ol, Guaia-5(6)-en-11-ol, Aciphyllene, 1-epi-Melicodenones C and E, and Other Guaiane-Type Sesquiterpenoids via the Diastereoselective Epoxidation of Guaiol

  摘要：

  The diastereomeric ratio of epoxidation of the internally bridged carbon-carbon double bond of guaiol (1a) is strongly influenced by the combined effects of the types of remote protecting groups on the hydroxyisopropyl side chain, choice of solvent, and epoxidizing reagent. This observation has allowed us to devise concise stereoselective syntheses of a range of guaiane-type sesquiterpenoids via an epoxidation, ring-opening/elimination, and functionality manipulation sequence. Natural products guaia-4(5)-en-11-ol (2a), guaia-5(6)-en-11-ol (3), and aciphyllene (4a) and epimers of the recently isolated natural products, 1-epi-guaia-4(5)-en-11-ol (2b), 1-epi-aciphyllene (4b), and 1-epi-melicodenones C (5a) and E (6a), were synthesized in good yields in relatively few steps.

  DOI：

  10.1021/np500611z
• 作为产物：
  描述：

  在 sodium 作用下， 反应 12.0h， 以3.03 g的产率得到2-[(3S,3aS,5R,8S,8aS)-3,8-dimethylhexahydro-1H,4H-3a,8a-epoxyazulen-5-yl]propan-2-ol
  参考文献：
  名称：

  Synthesis of Guaia-4(5)-en-11-ol, Guaia-5(6)-en-11-ol, Aciphyllene, 1-epi-Melicodenones C and E, and Other Guaiane-Type Sesquiterpenoids via the Diastereoselective Epoxidation of Guaiol

  摘要：

  The diastereomeric ratio of epoxidation of the internally bridged carbon-carbon double bond of guaiol (1a) is strongly influenced by the combined effects of the types of remote protecting groups on the hydroxyisopropyl side chain, choice of solvent, and epoxidizing reagent. This observation has allowed us to devise concise stereoselective syntheses of a range of guaiane-type sesquiterpenoids via an epoxidation, ring-opening/elimination, and functionality manipulation sequence. Natural products guaia-4(5)-en-11-ol (2a), guaia-5(6)-en-11-ol (3), and aciphyllene (4a) and epimers of the recently isolated natural products, 1-epi-guaia-4(5)-en-11-ol (2b), 1-epi-aciphyllene (4b), and 1-epi-melicodenones C (5a) and E (6a), were synthesized in good yields in relatively few steps.

  DOI：

  10.1021/np500611z

文献信息

• The regio- and stereo- selective epoxidation of alkenes with methyl trioxorhenium and urea-hydrogen peroxide adduct
  作者：Todd R. Boehlow、Christopher D. Spilling

  DOI：10.1016/0040-4039(96)00423-6

  日期：1996.4

  Alkenes are expoxidized with methyltrioxorhenium and urea-hydrogen peroxide adduct in CH2Cl2 solution.

  烯烃在CH 2 Cl 2溶液中用甲基三氧or和尿素-过氧化氢加合物进行氧化。
• Revisiting the Chemistry of Guaiacwood Oil: Identification and Formation Pathways of 5,11- and 10,11-Epoxyguaianes
  作者：Loïc Tissandié、Marc Gaysinski、Hugues Brévard、Uwe J. Meierhenrich、Jean-Jacques Filippi

  DOI：10.1021/acs.jnatprod.6b01068

  日期：2017.2.24

  ingredient, guaiacwood oil has not been extensively studied. Thus, the chemical characterization of its constituents by using a full array of GC-hyphenated techniques (GC-MS, GC × GC-MS, and pc-GC) combined with conventional chemical fractionation was undertaken. In the course of this work, 15 new sesquiterpenoids mostly belonging to the 5,11- and 10,11-epoxyguaiane families were identified. Each isolated

  从Guaiacwood油玉檀木洛伦兹前 Griseb是香精行业中常用的天然成分，因其高度赞赏的木香-玫瑰味以及出色的固定性能而在家用和豪华香精中使用。尽管愈创木油长期用作香料成分，但尚未对其进行广泛的研究。因此，通过使用一整套GC联用技术（GC-MS，GC×GC-MS和pc-GC）与常规化学分馏相结合，对其成分进行了化学表征。在这项工作的过程中，发现了15个新的倍半萜类化合物，它们主要属于5,11-和10,11-环氧瓜类家族。每种分离的化合物均通过NMR和MS进行了全面表征。总的来说，
• Trikojus; White, Journal and Proceedings - Royal Society of New South Wales, 1934, vol. 68, p. 177,181
  作者：Trikojus、White

  DOI：——

  日期：——
• Pesnelle, Recherches, 1966, # 15, p. 33,37
  作者：Pesnelle

  DOI：——

  日期：——
• Synthesis of Guaia-4(5)-en-11-ol, Guaia-5(6)-en-11-ol, Aciphyllene, 1-<i>epi</i>-Melicodenones C and E, and Other Guaiane-Type Sesquiterpenoids via the Diastereoselective Epoxidation of Guaiol
  作者：An-Cheng Huang、Christopher J. Sumby、Edward R. T. Tiekink、Dennis K. Taylor

  DOI：10.1021/np500611z

  日期：2014.11.26

  The diastereomeric ratio of epoxidation of the internally bridged carbon-carbon double bond of guaiol (1a) is strongly influenced by the combined effects of the types of remote protecting groups on the hydroxyisopropyl side chain, choice of solvent, and epoxidizing reagent. This observation has allowed us to devise concise stereoselective syntheses of a range of guaiane-type sesquiterpenoids via an epoxidation, ring-opening/elimination, and functionality manipulation sequence. Natural products guaia-4(5)-en-11-ol (2a), guaia-5(6)-en-11-ol (3), and aciphyllene (4a) and epimers of the recently isolated natural products, 1-epi-guaia-4(5)-en-11-ol (2b), 1-epi-aciphyllene (4b), and 1-epi-melicodenones C (5a) and E (6a), were synthesized in good yields in relatively few steps.