2-methylene-5-(1-methylethenyl)cyclohexanol | 2102-62-7

• 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-methylene-5-(1-methylethenyl)cyclohexanol
• 英文别名: isocarveol；p-mentha-1(7),8-dien-2-ol；2-Methylen-5-isopropenyl-cyclohexan-1-ol；(2S,4R)-p-Mentha-1(7),8-dien-2-ol；2-methylidene-5-prop-1-en-2-ylcyclohexan-1-ol
• CAS: 2102-62-7
• 化学式: C₁₀H₁₆O
• mdl: MFCD24392773
• 分子量: 152.236
• InChiKey: PNVTXOFNJFHXOK-UHFFFAOYSA-N

物化性质

• 沸点：
  227.4±40.0 °C(Predicted)
• 密度：
  0.92±0.1 g/cm3(Predicted)
• 保留指数：
  1186

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methylene-5-(1-methylethenyl)cyclohexanol 在 ammonium metavanadate 作用下， 反应 8.0h， 生成 紫苏醇
  参考文献：
  名称：

  Process for making perillyl alcohol

  摘要：

  揭示了一种制备过氧蒎醇的方法。该方法包括在100°C至220°C的温度范围内，在第5族金属催化剂的存在下使含有反式异香叶醇的起始物异构化，以产生过氧蒎醇。我们惊讶地发现，可以直接将反式异香叶醇异构化为过氧蒎醇，而反式异香叶醇可以从商业上可获得的顺式和反式LMO混合物中选择性地产生。当在惰性气氛和/或酚类抗氧化剂的存在下进行异构化时，过氧蒎醇的产量得到提高。在高沸点醇的存在下进行异构化或在高沸点醇的存在下从反应混合物中蒸馏过氧蒎醇产品，可以提高产量并最大限度地利用催化剂。所得的蒸馏残渣含有回收的第5族金属催化剂，对催化额外的反式异香叶醇异构化具有价值。

  公开号：

  US07851660B1
• 作为产物：
  描述：

  (R)-氧化柠檬烯 在 chromium octoate 2-氨基苯酚 作用下， 反应 1.5h， 生成 2-methylene-5-(1-methylethenyl)cyclohexanol
  参考文献：
  名称：

  Process for making perillyl alcohol

  摘要：

  揭示了一种制备过氧蒎醇的方法。该方法包括在100°C至220°C的温度范围内，在第5族金属催化剂的存在下使含有反式异香叶醇的起始物异构化，以产生过氧蒎醇。我们惊讶地发现，可以直接将反式异香叶醇异构化为过氧蒎醇，而反式异香叶醇可以从商业上可获得的顺式和反式LMO混合物中选择性地产生。当在惰性气氛和/或酚类抗氧化剂的存在下进行异构化时，过氧蒎醇的产量得到提高。在高沸点醇的存在下进行异构化或在高沸点醇的存在下从反应混合物中蒸馏过氧蒎醇产品，可以提高产量并最大限度地利用催化剂。所得的蒸馏残渣含有回收的第5族金属催化剂，对催化额外的反式异香叶醇异构化具有价值。

  公开号：

  US07851660B1

文献信息

• Heteropoly acid catalysts for the synthesis of fragrance compounds from biorenewables: isomerization of limonene oxide
  作者：Vinícius V. Costa、Kelly A. da Silva Rocha、Ivan V. Kozhevnikov、Elena F. Kozhevnikova、Elena V. Gusevskaya

  DOI：10.1039/c2cy20526b

  日期：——

  isomerization of limonene oxide was studied in the presence of heteropoly acid catalysts in aprotic solvents in homogeneous and heterogeneous systems. Among the catalysts were bulk and silica-supported tungstophosphoric acid H3PW12O40 and its acidic Cs salt Cs0.5H0.5PW12O40 (CsPW). The reaction gave dihydrocarvone, a valuable fragrance intermediate, as the main product with turnover numbers of up to

  液相异构化 氧化烯在均相和非均相系统中，在质子惰性溶剂中存在杂多酸催化剂的条件下，进行了研究。在催化剂中有本体和负载二氧化硅的钨磷酸H 3 PW 12 O 40及其酸性Cs盐Cs 0.5 H 0.5 PW 12 O 40（CsPW）。反应产生二氢香芹酮，一种有价值的香料中间体，作为主要产品，营业额高达8000。溶剂的性质对反应速率和选择性有很强的影响。发现CsPW（0.1 mol％）是该反应的高效且真正多相的催化剂，可提供82％的CsPW二氢香芹酮 在 1,4-二恶烷在环境条件下用作溶剂。这种简单的催化方法代表了从容易从香精油获得的生物可再生底物开始，向工业上重要的化合物发展的经济诱人途径。
• Spearmint flavor enhancer
  申请人：Symrise Inc.

  公开号：US10119096B2

  公开（公告）日：2018-11-06

  Spearmint flavor enhancers and methods for the production thereof. The spearmint flavor enhancers may include l-carvone, l-carveol isomers, and d-dihydrocarveol isomers. The spearmint flavor enhancers may further include l-isocarveol isomers, l-carvyl acetate isomers, d-dihydrocarvyl acetate isomers, and l-isocarvyl acetate isomers.

  薄荷增味剂及其生产方法。薄荷增味剂可包括 l-香芹酮、l-香芹醇异构体和 d-二氢香芹醇异构体。留兰香增味剂还可包括 l-异香芹醇异构体、l-乙酸香芹酯异构体、d-二氢香芹酯异构体和 l-乙酸异香芹酯异构体。
• Reversing baldness through follicle regeneration
  申请人：Postrel Richard

  公开号：US11331300B2

  公开（公告）日：2022-05-17

  This invention reverses male pattern baldness by shocking dormant hair follicles out of their androgen induced hibernation phase back to the active hair-growing anagenic phase. The invention integrates two functions: 1) It blocks synthesis of compounds holding the follicles in the telogenic/hibernating phase and 2) It stimulates synthesis of compounds animating the hair-growing/anagenic phase in the follicular activity cycle. One preferred embodiment comprises an enzyme inhibitor blocking the conversion of testosterone to dihydrotestosterone (DHT), a flavonoid simultaneously increasing synthesis of prostaglandins alternative to prostaglandin D2, and a selected cannabinoid compound stimulating restore the hair follicle to its normal growth cycle. This novel trimodal therapy restores the hair follicles to their normal cycling processes and maintains these restorative properties so long as this rebalance in maintained.

  本发明通过将休眠毛囊从雄性激素诱导的冬眠期震回到活跃的头发生长期，从而逆转男性型秃发。本发明集成了两种功能：1）阻止使毛囊处于休止期/冬眠期的化合物的合成；2）刺激毛囊活动周期中使毛发生长期/新生期活跃的化合物的合成。一个优选的实施方案包括：一种酶抑制剂，可阻止睾酮向双氢睾酮（DHT）的转化；一种类黄酮，可同时增加前列腺素 D2 替代物的合成；以及一种精选的大麻素化合物，可刺激毛囊恢复正常的生长周期。这种新颖的三联疗法能使毛囊恢复正常的循环过程，只要保持这种恢复平衡，就能保持这些恢复特性。
• Mixed disproportionation versus radical trapping in titanocene(III)-promoted epoxide openings
  作者：José Justicia、Tania Jiménez、Sara P. Morcillo、Juan M. Cuerva、J. Enrique Oltra

  DOI：10.1016/j.tet.2009.10.038

  日期：2009.12

  The formation of either deoxygenation products or allylic alcohols from epoxides is observed when these Substrates are treated with CP2TiCl under anhydrous conditions. It seems that processes via trisubstituted radicals give allylic alcohols whereas processes via disubstituted radicals may give deoxygenation products or allylic alcohols depending on the Structure of the original epoxide. This method allows a controlled access to these functional groups, providing a useful tool in organic synthesis. A mechanistic discussion for these transformations is reported. (c) 2009 Elsevier Ltd. All rights reserved.
• Thermal Degradation of Terpenes:  Camphene, Δ³-Carene, Limonene, and α-Terpinene
  作者：Gerald W. McGraw、Richard W. Hemingway、Leonard L. Ingram,、Catherine S. Canady、William B. McGraw

  DOI：10.1021/es9810641

  日期：1999.11.1

  Emissions from wood dryers have been of some concern for a number of years, and recent policy changes by the Environmental Protection Agency have placed emphasis upon the gaseous emissions that lead to the formation of particulate matter as small as 2.5 mu m diameter. in this qualitative study, camphene, Delta(3)-carene, limonene, and alpha-terpinene were thermally degraded in the presence of air to determine the number and kind of oxidative degradation products that might be expected under drying conditions used in processing wood products. Various chromatographic methods were used to isolate the products far proof of structure by NMR and/or GC-MS. The degradation products resulted from dehydrogenations, epoxidations, double bond cleavages, allylic oxidations, and rearrangements. A number of compounds not previously associated with the thermal degradation of these terpenes were identified.

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