[1AR-(1AAlpha,4AAlpha,7Alpha,8AAlpha)]-八氢-4,4,8,8-四甲基-4A,7-亚甲基-4AH-萘基[1,8A-B]环氧乙烯 | 26619-69-2

• 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
• 中文名称: [1AR-(1AAlpha,4AAlpha,7Alpha,8AAlpha)]-八氢-4,4,8,8-四甲基-4A,7-亚甲基-4AH-萘基[1,8A-B]环氧乙烯
• 中文别名: [1AR-(1Aα,4Aα,7α,8Aα)]-八氢-4,4,8,8-四甲基-4A,7-亚甲基-4AH-萘基[1,8A-B]环氧乙烯；环氧异长叶烯
• 英文名称: isolongifolene epoxide
• 英文别名: 4a,7-Methano-4aH-naphth[1,8a-b]oxirene, octahydro-4,4,8,8-tetramethyl-, (1aR,4aR,7S,8aS)-；(1R,5R,7S,9S)-2,2,8,8-tetramethyl-6-oxatetracyclo[7.2.1.01,7.05,7]dodecane
• CAS: 26619-69-2
• 化学式: C₁₅H₂₄O
• 分子量: 220.355
• InChiKey: VQHLGZRKOZIABH-DRABBMOASA-N

物化性质

• 熔点：
  39-41 °C
• 沸点：
  109-112 °C(Press: 5 Torr)
• 密度：
  1.04±0.1 g/cm3(Predicted)
• LogP：
  5.8 at 35℃

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  [1AR-(1AAlpha,4AAlpha,7Alpha,8AAlpha)]-八氢-4,4,8,8-四甲基-4A,7-亚甲基-4AH-萘基[1,8A-B]环氧乙烯 在 三氟化硼 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 0.02h， 生成 7αH-8-oxoisolongifolane
  参考文献：
  名称：

  Structure elucidation of oxidation-reduction products of isolongifolene

  摘要：

  Three alcohol isomers have been synthesized in high yield from isolongifolene to provide easy-to-make and cheap odorants. Oxidation of isolongifolene by reaction with m-chloroperbenzoic acid yielded a mixture of the corresponding epoxide, ketone, and alcohol. Two other alcohols were obtained from the reduction of the epoxide and the ketone, respectively. An herbal, spicy, and earthy odor was detected from the ketone and alcohols. The structural formulas of the compounds were determined using one-and two-dimensional NMR and gas chromatography-mass spectrometry.

  DOI：

  10.1021/jf00037a024
• 作为产物：
  描述：

  异长叶烯 在 氧气 、 manganese triacetate 、 特戊醛 作用下， 以 甲苯 为溶剂， 以64%的产率得到[1AR-(1AAlpha,4AAlpha,7Alpha,8AAlpha)]-八氢-4,4,8,8-四甲基-4A,7-亚甲基-4AH-萘基[1,8A-B]环氧乙烯
  参考文献：
  名称：

  氟相合成：异长叶环氧化物的便利合成及其重排成酮

  摘要：

  在存在Mn（OAc）3 ·2H 2 O作为催化剂的情况下，在全氟-2-丁基四氢呋喃（FC-75）中，用新戊醛/氧气对异长叶环烯1进行好氧环氧化，得到高收率的异长叶环氧化物3。实现了异longifolene-β-环氧化物重排为酮4。

  DOI：

  10.1016/s0022-1139(99)00243-2

文献信息

• Pd-Catalyzed aerobic oxidation of the sesquiterpene isolongifolene: A green and heterogeneous process
  作者：Carla Nunes de Melo、Yuri Blanc Rodrigues、Patrícia Alejandra Robles-Azocar

  DOI：10.1016/j.ica.2020.120192

  日期：2021.3

  Abstract The oxidation of the sesquiterpene isolongifolene, catalyzed by Pd/SiO2 prepared through a conventional sol–gel method, resulted mainly in isolongifolen-9-one (65% selectivity), a compound which occupies a prominent place in perfume industry. In addition to the product obtained from the allylic oxidation of isolongifolene, the formation of other oxygenated products with potential industrial

  摘要以传统的溶胶-凝胶法制备的Pd / SiO2催化倍半萜烯异长叶烯的氧化，主要产生异长叶烯-9-1（选择性为65％），该化合物在香水工业中占有重要地位。除了由异长叶烯的烯丙基氧化得到的产物外，还观察到了其他具有潜在工业应用的氧化产物的形成（两者的总收率均为94％）。该系统可用于其他倍半萜烯，瓦伦烯的氧化。在这种情况下，有可能获得含氧产物，产率高达66％。该反应在温和条件下在绿色多相氧化催化体系中发生。在不存在助氧化剂的情况下，将Pd（II）用作单独催化剂。
• Krishna, R. R.; Chawla, H. P. S.; Dev, Sukh, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 12, p. 1190 - 1196
  作者：Krishna, R. R.、Chawla, H. P. S.、Dev, Sukh

  DOI：——

  日期：——
• Nayak, U. R.; Dalavoy, V. S.; Deodhar, V. B., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 891 - 893
  作者：Nayak, U. R.、Dalavoy, V. S.、Deodhar, V. B.

  DOI：——

  日期：——
• Structure elucidation of oxidation-reduction products of isolongifolene
  作者：Isabelle Bombarda、Jacqueline Smadja、Emile M. Gaydou、Jacques Yves Conan、Robert Faure

  DOI：10.1021/jf00037a024

  日期：1994.1

  Three alcohol isomers have been synthesized in high yield from isolongifolene to provide easy-to-make and cheap odorants. Oxidation of isolongifolene by reaction with m-chloroperbenzoic acid yielded a mixture of the corresponding epoxide, ketone, and alcohol. Two other alcohols were obtained from the reduction of the epoxide and the ketone, respectively. An herbal, spicy, and earthy odor was detected from the ketone and alcohols. The structural formulas of the compounds were determined using one-and two-dimensional NMR and gas chromatography-mass spectrometry.
• Synthesis in fluorous phase: a convenient synthesis of isolongifolene epoxide and its rearrangement to ketone
  作者：K.S. Ravikumar、Jean-Pierre Bégué、Danièle Bonnet-Delpon、Michèle Ourévitch

  DOI：10.1016/s0022-1139(99)00243-2

  日期：2000.3

  Aerobic epoxidation of isolongifolene 1 with pivalaldehyde/oxygen in perfluoro-2-butyltetrahydrofuran (FC-75) in the presence of Mn(OAc)3·2H2O as catalyst yielded isolongifolene-epoxide 3 in good yield. The rearrangement of isolongifolene-β-epoxide to ketone 4 was achieved.

  在存在Mn（OAc）3 ·2H 2 O作为催化剂的情况下，在全氟-2-丁基四氢呋喃（FC-75）中，用新戊醛/氧气对异长叶环烯1进行好氧环氧化，得到高收率的异长叶环氧化物3。实现了异longifolene-β-环氧化物重排为酮4。