2-carene-4-one | 28226-49-5

• 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-carene-4-one
• 英文别名: (+)-car-2-en-4-one；4,7,7-trimethyl-bicyclo[4.1.0]-4-hepten-3-one；4-carene；2-Caren-4-one；4,7,7-trimethylbicyclo[4.1.0]hept-4-en-3-one
• CAS: 28226-49-5
• 化学式: C₁₀H₁₄O
• 分子量: 150.221
• InChiKey: CTZWGIMYGKDLPH-UHFFFAOYSA-N

物化性质

• 沸点：
  217.1±7.0 °C(Predicted)
• 密度：
  0.992±0.06 g/cm3(Predicted)
• 保留指数：
  1215

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  2-carene-4-one 、 甲基锂 生成 3,4,7,7-Tetramethylbicyclo[4.1.0]hept-4-en-3-ol
  参考文献：
  名称：

  HO, T. L.;DIN, ZIA, U.

  摘要：

  DOI：
• 作为产物：
  描述：

  2-carene 在 selenium(IV) oxide 、 pinane hydroperoxide 、 溶剂黄146 作用下， 以 二氯甲烷 、 氯苯 为溶剂， 生成 [1S-(1a,3a,6a)]-3,7,7-三甲基-二环[4.1.0]-4-庚烯-3-醇 、 2-carene-4-one
  参考文献：
  名称：

  Metal-Catalyzed Oxidations with Pinane Hydroperoxide:  A Mechanistic Probe To Distinguish between Oxometal and Peroxometal Pathways

  摘要：

  The relative reactivities of tert-butyl hydroperoxide (TBHP) and pinane hydroperoxide (PHP) in metal (Cr, Mo, Ru, Se, V, and Zr)-catalyzed oxidations were compared. When these oxidations involve rate-limiting oxygen transfer from a peroxometal species to the substrate huge differences between TBHP and PHP were observed, e.g., molybdenum-catalyzed epoxidation of cyclohexene with TBHP gave a 98% yield while PHP gave 0%. When the reaction involves reaction of an oxometal species with the substrate as the rate-limiting step, little or no difference is observed, e.g., the selenium-catalyzed allylic oxidation of beta-pinene gave a 96% and 99% yield with TBHP and PHP, respectively. Small but significant differences are observed when reoxidation of the catalyst by the hydroperoxide to the active oxometal species is the rate-limiting step; e.g., the chromium-catalyzed oxidation of carveol gave carvone in 89% and 24% yield with TBHP and PHP, respectively. Hence, the effect of RO2H structure on rate is dependent on the rate-limiting step.

  DOI：

  10.1021/jo971270b

文献信息

• 一种由3-蒈烯制备3-异丙基-5-甲酚和香芹酚 的方法
  申请人：中国林业科学研究院林产化学工业研究所

  公开号：CN109232193B

  公开（公告）日：2021-09-17

  本发明公开了一种由3‑蒈烯制备3‑异丙基‑5‑甲酚和香芹酚的方法。3‑蒈烯在CrO3‑Al2O3催化下，与氧气于室温下反应生成产物Ⅰ：主要组分包括5‑蒈酮、2‑蒈酮和4‑蒈酮，3种酮类产物选择性比约为10.8:3.5:1.0；产物Ⅰ经蒸馏回收3‑蒈烯，回收率大于80%，回收纯度大于94%；剩余组分在13X型分子筛催化下于230℃转化为产物Ⅱ：主要组分包括3‑异丙基‑5‑甲酚和香芹酚，原料转化率100%，酚类产物总选择性可达98%，2种酚类产物选择性比约为2.2:1.0，减压蒸馏产物Ⅱ得到一种纯度大于96%的混合酚产品；产物Ⅱ作柱层析分离，分别得到纯度大于97%的3‑异丙基‑5‑甲酚和香芹酚。
• Preparation of (-)-dihydrochrysanthemolactone
  申请人：SCM Corporation

  公开号：US04296038A1

  公开（公告）日：1981-10-20

  A four-step process for producing (-)-dihydrochrysanthemolactone from 2-caren-4-one is disclosed. The four steps in order are methylating 2-caren-4-one, oxidizing, methylating the tautomeric mixture resulting from the oxidation, and finally lactonizing the single hydroxy acid resulting from the second methylation. Additionally, three novel intermediate compounds that are produced by the steps in the process are disclosed.

  公开了从2-卡伦-4-酮制备(-)-双氢菊烯内酯的四步过程。这四个步骤依次为：甲基化2-卡伦-4-酮，氧化，甲基化氧化产物的互变异构体混合物，最后内酯化第二次甲基化产生的单一羟基酸。此外，还公开了由过程中的步骤产生的三种新型中间化合物。
• Cobalt- and manganese-substituted ferrites as efficient single-site heterogeneous catalysts for aerobic oxidation of monoterpenic alkenes under solvent-free conditions
  作者：L MENINI、M PEREIRA、L PARREIRA、J FABRIS、E GUSEVSKAYA

  DOI：10.1016/j.jcat.2008.01.013

  日期：2008.3.10

  Cobalt- and manganese-substituted ferrites were used as heterogeneous catalysts for liquid-phase aerobic oxidation of various monoterpenic alkenes. The materials were prepared by co-precipitation and characterized by Mossbauer spectroscopy, powder X-ray diffractometry, magnetization measurements, and elemental analysis. The results show that isomorphic substitution of iron in the ferrite crystalline structure occurred preferentially at octahedral positions and strongly affected its catalytic properties in the oxidation of monoterpenes. Various valuable oxygenated monoterpenic compounds were obtained with high combined selectivities (75-95%) at ca. 40% substrate conversions. Oxidations of beta-pinene and 3-carene led almost exclusively to allylic mono-oxygenated derivatives, whereas limonene and alpha-pinene gave both epoxides and allylic products. The use of inexpensive catalyst and oxidant, solvent-free conditions, and high final product concentrations (ca. 40 wt%) are significant practical advantages of this environmentally friendly process. The catalysts undergo no metal leaching and can be easily recovered by the application of an external magnet and reused. (C) 2008 Elsevier Inc. All rights reserved.
• Pandita, K.; Thappa, R. K.; Agarwal, S. G., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 8, p. 763 - 765
  作者：Pandita, K.、Thappa, R. K.、Agarwal, S. G.、Dhar, K. L.、Atal, C. K.

  DOI：——

  日期：——
• BHAT N. G.; PAI P. P.; KULKARNI G. H., CHEM. AND IND., 1981, NO 3, 94-95
  作者：BHAT N. G.、 PAI P. P.、 KULKARNI G. H.

  DOI：——

  日期：——