(1S,5S)-2-甲亚基-5-(丙-1-烯-2-基)环己醇 | 102917-36-2

• 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: (1S,5S)-2-甲亚基-5-(丙-1-烯-2-基)环己醇
• 英文名称: (1S,5S)-5-isopropenyl-2-methylenecyclohexan-1-ol
• 英文别名: cis-exo-carveol；cis-isocarveol；cis-p-Mentha-1(7),8-dien-2-ol；Cyclohexanol, 2-methylene-5-(1-methylethenyl)-, (1S-cis)-；(1S,5S)-2-methylidene-5-prop-1-en-2-ylcyclohexan-1-ol
• CAS: 102917-36-2
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: PNVTXOFNJFHXOK-UWVGGRQHSA-N

物化性质

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

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

• 作为产物：
  描述：

  (1S,5S)-5-Isopropenyl-2-methylene-cyclohexyl-hydroperoxide 在 三苯基膦 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以6 mg的产率得到(1S,5S)-2-甲亚基-5-(丙-1-烯-2-基)环己醇
  参考文献：
  名称：

  Monoterpene Hydroperoxides with Trypanocidal Activity from Chenopodium ambrosioides

  摘要：

  Four monoterpene hydroperoxides were isolated from aerial parts of Chenopodium ambrosioides along with ascaridole (1), the anthelmintic principle of this plant, as anti-trypanosomal compounds. The structures of these monoterpenes were determined to be (-)-(2S,4S)- and (-)-(2R,4S)-p-mentha-1(7),8-dien-2-hydroperoxide (2a and 3a) and (-)-(1R,4S)- and (-)-(1S,4S)-p-mentha-2,8-dien-1-hydroperoxide (4a and 5a) on the basis of spectroscopic methods and chemical correlations. In vitro trypanocidal activities of ascaridole (1) and these hydroperoxides (2a-5a) against epimastigotes of Trypanosoma cruzi were 23, 1.2, 1.6, 3.1, and 0.8 muM, respectively. Fresh leaves of C. ambrosioides also contained isomeric hydroperoxides 6a and 7a, and the content ratio of 2a-7a suggested that these hydroperoxides were formed through the singlet-oxygen oxidation of limonene.

  DOI：

  10.1021/np010445g

文献信息

• Singlet Oxygen Mediated Oxidation of Olefins within Zeolites: Selectivity and Complexities
  作者：J. Shailaja、J. Sivaguru、Rebecca J. Robbins、V. Ramamurthy、R.B. Sunoj、J. Chandrasekhar

  DOI：10.1016/s0040-4020(00)00513-5

  日期：2000.9

  trisubstituted alkenes, hydroperoxidation within zeolites occurs with a certain amount of regioselectivity. The oxidation within zeolites is accompanied by photodecomposition of the dye and the product hydroperoxides and acid catalyzed rearrangement of the alkenes. In order to understand the observed selectivity, ab initio and DFT calculations on model systems have been performed. The calculations

  噻嗪染料，例如硫蛋白，亚甲基蓝和亚甲基绿已经在单价阳离子交换的Y型沸石中进行了阳离子交换。取决于水含量，染料分子以单体（“干”）或二聚体（“湿”）的形式存在。单体染料在可见光激发下产生单线态氧，该单线态氧已被用于将烯烃氧化为氢过氧化物。在三取代烯烃的情况下，沸石内的加氢过氧化反应具有一定的区域选择性。沸石内的氧化伴随着染料和产物氢过氧化物的光分解以及烯烃的酸催化重排。为了理解观察到的选择性，已经在模型系统上进行了从头算和DFT计算。这些计算证实了阳离子-烯烃键合相当强，以及其他几何和轨道畸变。计算得出的用于氢提取的活化能表明由于金属配位而导致明显的速率延迟。在MP2和B3LYP水平上，计算出由2-甲基2-丁烯的甲基（4-位）夺氢形成叔氢过氧化物的可能性很小。在宝石二甲基单元之间，从与反式对应物相比，顺式甲基略受青睐。这些预测与观察到的区域选择性不兼容。正在进行进一步的实验和理论研究，以了解在沸石中观察到的区域选择性氧化。
• [EN] (+)-TRANS TETRAHYDROCANNABINOL ((+)-TRANS-THC) FOR USE AS A MEDICAMENT<br/>[FR] UTILISATION DE (+)-TRANS TÉTRAHYDROCANNABINOL ((+)-TRANS-THC) COMME MÉDICAMENT
  申请人：GW RES LTD

  公开号：WO2021079137A1

  公开（公告）日：2021-04-29

  The present invention relates to a tetrahydrocannabinol (THC) type cannabinoid compound for use as a medicament. The THC-type cannabinoid is an enantiomer of the (-)-trans- tetrahydrocannabinol which is a naturally occurring cannabinoid that can be found in cannabis plant strains which have been bred to yield THC as the dominant cannabinoid. The particular enantiomer (+)-trans tetrahydrocannabinol has been found to have properties which are different from the naturally occurring (-)-trans-THC. The cannabinoid (+)-trans-THC has been found to occur in low concentrations in particular cannabis plant strains. Furthermore, the cannabinoid can be produced by synthetic means.

  本发明涉及一种用作药物的四氢大麻酚（THC）类大麻素化合物。该THC类大麻素是(-)-反式四氢大麻酚的对映体，后者是一种天然存在的大麻素，可在经过育种以产生THC为主要大麻素的大麻植物品种中发现。特定的对映体(+)-反式四氢大麻酚已被发现具有与天然存在的(-)-反式THC不同的性质。大麻素(+)-反式THC已被发现以低浓度存在于特定的大麻植物品种中。此外，该大麻素可以通过合成手段生产。
• Process for making trans-isocarveol
  申请人：LyondellBasell Flavors & Fragrances, LLC

  公开号：US07884252B1

  公开（公告）日：2011-02-08

  A process for making trans-isocarveol, an intermediate useful in the manufacture of perillyl alcohol, is disclosed. The process comprises isomerizing a mixture comprising cis-limonene oxide (cis-LMO) and trans-limonene oxide (trans-LMO) in the presence of a phenolic modifier and a chromium catalyst. The process is performed at a temperature less than 220° C. to convert more than 50% of the cis-LMO to trans-isocarveol and less than 50% of the trans-LMO to cis-isocarveol. We surprisingly found that a mixture of cis- and trans-LMO can be selectively isomerized to produce mostly trans-isocarveol, which we discovered is the preferred isomer for making perillyl alcohol by direct isomerization.

  揭示了一种制备过渡型异卡维醇的方法，该中间体在制造佩里醇时有用。该方法包括在酚类改性剂和铬催化剂的存在下异构化包含顺-柠檬烯氧化物（顺-LMO）和反-柠檬烯氧化物（反-LMO）的混合物。该过程在低于220°C的温度下进行，将超过50％的顺-LMO转化为反-异卡维醇，将少于50％的反-LMO转化为顺-异卡维醇。我们惊奇地发现，顺-和反-LMO的混合物可以选择性地异构化，以产生大多数反-异卡维醇，我们发现这是通过直接异构化制造佩里醇的首选异构体。
• Jayasree; Narayanan, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1997, vol. 36, # 1, p. 9 - 13
  作者：Jayasree、Narayanan

  DOI：——

  日期：——
• US7851660B1
  申请人：——

  公开号：US7851660B1

  公开（公告）日：2010-12-14