(+)-nerolidol | 77171-59-6

• 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: (+)-nerolidol
• 英文别名: nerolidol；(S)-(+)-Nerolidol；(3S)-3,7,11-trimethyldodeca-1,6,10-trien-3-ol
• CAS: 77171-59-6
• 化学式: C₁₅H₂₆O
• mdl: MFCD00085350
• 分子量: 222.371
• InChiKey: FQTLCLSUCSAZDY-OAHLLOKOSA-N

物化性质

• 沸点：
  276.0±0.0 °C(Predicted)
• 密度：
  0.869±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)
• 物理描述：
  Colourless or very pale straw-coloured oily liquid; Faint woody-floral, slightly rose apple aroma
• 溶解度：
  Soluble in most fixed oils and propylene glycol; slightly soluble in water; insoluble in glycerol
• 折光率：
  1.478-1.483

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• 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：

  (+)-nerolidol 在 二氯二茂钛 、 锰 、 bis(acetylacetonate)oxovanadium 、 三乙胺 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 0.59h， 生成 (+)-1-hydroxychokol K
  参考文献：
  名称：

  Protecting-Group-Free Synthesis of Chokols

  摘要：

  As a result of a combined theoretical and experimental study, we describe a two-step protocol for the preparation of an optically pure, multifunctional, cyclopentanic core shared by a number of natural products. This process is based on a hitherto unreported Ti(III)-mediated diastereoselective cyclization in which the hydroxy-directed template effect played by the Ti(III) species was found to be crucial for the stereoselective outcome of the reaction. The viability of this concept was confirmed with the first protecting-group free synthesis of three enantiopure chokols, namely, chokols K, E, and B.

  DOI：

  10.1021/jo102280n

文献信息

• Biomimetic Synthesis of (+)-Neroplofurol
  作者：Xing Huo、Xinfu Pan、Guosheng Huang、Xuegong She

  DOI：10.1055/s-0030-1259943

  日期：2011.5

  (+)-Neroplofurol was biomimetically synthesized in only two steps from natural (+)-nerolidol via Sharpless dihydroxylation and a cascade Shi epoxidation/epoxide ring-opening reaction. All carbons are derived from natural (+)-nerolidol and no protecting groups were utilized, making the synthesis atom-economical and highly efficient. The synthetic neroplofurol was proved to be the enantiomer of the natural one, according to ¹H NMR, ¹³C NMR spectra and optical rotation value. The absolute configuration of natural neroplofurol was also deduced to be 3R,6S,7R,10S.

  (+)-Neroplofurol 是由天然 (+)-nerolidol 通过 Sharpless 二羟基反应和级联 Shi 环氧化/环氧化物开环反应仅用两个步骤生物模拟合成的。所有碳都来自天然 (+)-nerolidol 而且没有使用保护基团，从而使合成过程具有原子经济性和高效性。根据¹H NMR、¹³C NMR 光谱和旋光度值，证明合成的橙花呋喃是天然橙花呋喃的对映体。天然橙花呋喃的绝对构型也被推断为 3R,6S,7R,10S。
• Hydroaminomethylation of Natural Allylic and Homoallylic Alcohols: A Ligand‐Controlled Route to New Amines
  作者：Adelson de O. Dias、Alexandra G. Santos、Fábio G. Delolo、Jesus A. Avendaño‐Villarreal、Eduardo N. dos Santos、Elena V. Gusevskaya

  DOI：10.1002/cctc.202201113

  日期：2023.1.20

  low-cost hydroxyolefins allows accessing structurally complex amines of pharmaceutical relevance. Through the appropriate choice of auxiliary phosphorus ligands this tandem catalytic process can be directed to the formation of two different types of amines: aminoalcohols or aminotetrahydrofurans and aminotetrahydropyrans (starting from allylic and homoallylic alcohols, respectively).

  氢氨甲基化 (HAM) 是一种串联催化过程，允许从烯烃骨架中获取胺，并且完全符合绿色化学规则。在这项工作中，HAM 被应用于天然羟基烯烃：异戊二烯醇、芳樟醇、橙花醇和异胡薄荷醇。使用 4-甲基哌啶、吗啉和 1,2,3,4-四氢异喹啉作为对应物，从生物可再生的低成本底物制备了几种结构复杂的新型胺，为利用这种结构多样性的生物活性开辟了道路。通过适当的选择基于菱形的催化系统以及反应条件，可以实现每个对应物的必要微调。未促进的铑系统主要导致氨基醇，
• Protecting-Group-Free Synthesis of Chokols
  作者：Carmen Pérez Morales、Julieta Catalán、Victoriano Domingo、José A. González Delgado、José A. Dobado、M. Mar Herrador、José F. Quílez del Moral、Alejandro F. Barrero

  DOI：10.1021/jo102280n

  日期：2011.4.15

  As a result of a combined theoretical and experimental study, we describe a two-step protocol for the preparation of an optically pure, multifunctional, cyclopentanic core shared by a number of natural products. This process is based on a hitherto unreported Ti(III)-mediated diastereoselective cyclization in which the hydroxy-directed template effect played by the Ti(III) species was found to be crucial for the stereoselective outcome of the reaction. The viability of this concept was confirmed with the first protecting-group free synthesis of three enantiopure chokols, namely, chokols K, E, and B.