(+)-Sabinone

• 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: (+)-Sabinone
• 英文别名: (1S,5S)-4-methylidene-1-propan-2-ylbicyclo[3.1.0]hexan-3-one
• 化学式: C₁₀H₁₄O
• 分子量: 150.221
• InChiKey: PBLWMCQDAGOTPV-SCZZXKLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  1
• 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：

  (+)-Sabinone 、 bis(trimethylsilylmethyl)sulfoxide 23.0 ℃ 、1.4 MPa 条件下， 反应 2.0h， 以78%的产率得到
  参考文献：
  名称：

  通过硫代羰基叶立德的[3+2]-环加成合成多官能化分子

  摘要：

  在这里，我们对硫代羰基叶立德与各种烯烃和炔烃的[3+2]-环加成进行了全面的研究。所获得的二氢和四氢噻吩产品作为用途极其广泛的中间体，提供了获得噻吩、二烯、树枝烯和八元碳中心的途径。高压条件的使用使得热不稳定、空间阻碍或中等反应性的底物能够在温和条件下进行环加成，从而将产率提高高达 58%。此外，我们还通过药物 NGB 4420 和替尼拉平的正式合成展示了其实用性。

  DOI：

  10.1021/jacs.9b07729
• 作为产物：
  描述：

  (+)-桧烯 在 叔丁基过氧化氢 、 manganese(IV) oxide 、 selenium(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (+)-Sabinone
  参考文献：
  名称：

  α-和β-Thujones（草药和食品添加剂）：羟基和脱氢代谢产物的合成和分析。

  摘要：

  含有α-和β-丁二烯的精油是重要的草药和食品添加剂。丁二酮非对映异构体是迅速代谢的惊厥剂，充当γ-氨基丁酸门控氯离子通道的非竞争性阻滞剂。代谢物的合成和分析是了解其健康影响的重要步骤。用过二氧过氧钼（吡啶）（六甲基磷酸三酰胺）氧化α-和β-thujones2,3烯酸酯，得到相应的（2R）-2-羟基thujones，由（1）H和（13）C NMR和X射线确定晶体学。在分别用过酸和四氧化氧化后，通过3,4-烯醇乙酸酯将α-丁酮转化为4-羟基-α-和-β-丁二酮。臭氧化提供了7-羟基-α-和-β-thujones，并且通过脱水提供了7,8-脱氢化合物。4，由sa木烯经sa木酚制备10-脱氢thuthone。羟基和脱氢衍生物很容易鉴定，并通过GC / MS分析为母体化合物以及三甲基甲硅烷基和甲基肟衍生物。另一项研究确定，所有这些化合物都是α-和β-丁二烯的代谢产物。

  DOI：

  10.1021/jf001445+

文献信息

• Metabolism of monoterpenes: Specificity of the dehydrogenases responsible for the biosynthesis of camphor, 3-thujone, and 3-lsothujone
  作者：Shangara S. Dehal、Rodney Croteau

  DOI：10.1016/0003-9861(87)90346-8

  日期：1987.10

  electrophoretically distinct dehydrogenases for the respective oxidations of (+)-borneol to (+)-camphor, and of (+)-cis-sabinol to (+)-sabinone en route to (-)-3-isothujone. Similarly, tansy (Tanacetum vulgare) is shown to contain two electrophoretically distinct dehydrogenases for the respective oxidations of (-)-borneol to (-)-camphor and of (+)-cis-sabinol to (+)-sabinone en route to (+)-3-thujone. These results

  鼠尾草（Salvia officinalis）被证明含有两个电泳上不同的脱氢酶，分别用于将（+）-冰片醇氧化为（+）-樟脑，以及将（+）-顺式-沙宾醇氧化为（+）-沙比农酮，然后再氧化为（- ）-3-isothujone。相似地，艾菊（艾菊（Tanacetum vulgare））被证明包含两种电泳上不同的脱氢酶，分别用于将（-）-冰片醇氧化为（-）-樟脑，以及将（+）-顺式香薄荷醇氧化为（+）-香椿酮。 +）-3-thujone。这些结果表明，单独的脱氢酶负责从冰片中合成樟脑和通过顺式沙宾醇进行丁苯乙酮的生物合成，并且它们还表明，先前报道的各种冰片酚被冰片脱氢酶氧化只是与形成无关的巧合活动。 3-thujone和3-isothujone。
• Probe Compound for Detecting and Isolating Enzymes and Means and Methods Using the Same
  申请人：Golyshin Peter N.

  公开号：US20120231972A1

  公开（公告）日：2012-09-13

  The present invention relates to a probe compound that can comprise any substrate or metabolite of an enzymatic reaction in addition to an indicator component, such as, for example, a fluorescence dye, or the like. Moreover, the present invention relates to means for detecting enzymes in form of an array, which comprises any number of probe compounds of the invention which each comprise a different metabolite of interconnected metabolites representing the central pathways in all forms of life. Moreover, the present invention relates to a method for detecting enzymes involving the application of cell extracts or the like to the array of the invention which leads to reproducible enzymatic reactions with the substrates. These specific enzymatic reactions trigger the indicator (e.g. a fluorescence signal) and bind the enzymes to the respective cognate substrates. Moreover, the invention relates to means for isolating enzymes in form of nanoparticles coated with the probe compound of the invention. The immobilisation of the cognate substrates or metabolites on the surface of nanoparticles by means of the probe compounds allows capturing and isolating the respective enzyme, e.g. for subsequent sequencing.
• [EN] PROBE COMPOUND FOR DETECTING AND ISOLATING ENZYMES AND MEANS AND METHODS USING THE SAME<br/>[FR] COMPOSÉ SONDE POUR DÉTECTER ET ISOLER DES ENZYMES ET MOYENS ET PROCÉDÉS POUR L'UTILISER
  申请人：HELMHOLTZ INFEKTIONSFORSCHUNG

  公开号：WO2010105851A1

  公开（公告）日：2010-09-23

  The present invention relates to a probe compound that can comprise any substrate or metabolite of an enzymatic reaction in addition to an indicator component, such as, for example, a fluorescence dye, or the like. Moreover, the present invention relates to means for detecting enzymes in form of an array, which comprises any number of probe compounds of the invention which each comprise a different metabolite of interconnected metabolites representing the central pathways in all forms of life. Moreover, the present invention relates to a method for detecting enzymes involving the application of cell extracts or the like to the array of the invention which leads to reproducible enzymatic reactions with the substrates. These specific enzymatic reactions trigger the indicator (e.g. a fluorescence signal) and bind the enzymes to the respective cognate substrates. Moreover, the invention relates to means for isolating enzymes in form of nanoparticles coated with the probe compound of the invention. The immobilisation of the cognate substrates or metabolites on the surface of nanoparticles by means of the probe compounds allows capturing and isolating the respective enzyme, e.g. for subsequent sequencing.
• Synthetic Entry to Polyfunctionalized Molecules through the [3+2]-Cycloaddition of Thiocarbonyl Ylides
  作者：Franz-Lucas Haut、Christoph Habiger、Klaus Speck、Klaus Wurst、Peter Mayer、Johannes Nepomuk Korber、Thomas Müller、Thomas Magauer

  DOI：10.1021/jacs.9b07729

  日期：2019.8.28

  Here we present a comprehensive study on the [3+2]-cycloaddition of thiocarbonyl ylides with a wide variety of alkenes and alkynes. The obtained dihydro- and tetrahydrothiophenes products serve as exceptionally versatile intermediates providing access to thiophenes, dienes, dendralenes, and vic-quarternary carbon centers. The use of high-pressure conditions enables thermally unstable, sterically encumbered

  在这里，我们对硫代羰基叶立德与各种烯烃和炔烃的[3+2]-环加成进行了全面的研究。所获得的二氢和四氢噻吩产品作为用途极其广泛的中间体，提供了获得噻吩、二烯、树枝烯和八元碳中心的途径。高压条件的使用使得热不稳定、空间阻碍或中等反应性的底物能够在温和条件下进行环加成，从而将产率提高高达 58%。此外，我们还通过药物 NGB 4420 和替尼拉平的正式合成展示了其实用性。
• α- and β-Thujones (Herbal Medicines and Food Additives):  Synthesis and Analysis of Hydroxy and Dehydro Metabolites
  作者：Nilantha S. Sirisoma、Karin M. Höld、John E. Casida

  DOI：10.1021/jf001445+

  日期：2001.4.1

  acting as noncompetitive blockers of the gamma-aminobutyric acid-gated chloride channel. Synthesis and analysis of the metabolites are essential steps in understanding their health effects. Oxidation of alpha- and beta-thujones as their 2,3-enolates with oxodiperoxymolybdenum(pyridine)(hexamethylphosphoric triamide) gave the corresponding (2R)-2-hydroxythujones assigned by (1)H and (13)C NMR and X-ray

  含有α-和β-丁二烯的精油是重要的草药和食品添加剂。丁二酮非对映异构体是迅速代谢的惊厥剂，充当γ-氨基丁酸门控氯离子通道的非竞争性阻滞剂。代谢物的合成和分析是了解其健康影响的重要步骤。用过二氧过氧钼（吡啶）（六甲基磷酸三酰胺）氧化α-和β-thujones2,3烯酸酯，得到相应的（2R）-2-羟基thujones，由（1）H和（13）C NMR和X射线确定晶体学。在分别用过酸和四氧化氧化后，通过3,4-烯醇乙酸酯将α-丁酮转化为4-羟基-α-和-β-丁二酮。臭氧化提供了7-羟基-α-和-β-thujones，并且通过脱水提供了7,8-脱氢化合物。4，由sa木烯经sa木酚制备10-脱氢thuthone。羟基和脱氢衍生物很容易鉴定，并通过GC / MS分析为母体化合物以及三甲基甲硅烷基和甲基肟衍生物。另一项研究确定，所有这些化合物都是α-和β-丁二烯的代谢产物。