(R)-octane-1,3-diol | 120727-18-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-octane-1,3-diol
• 英文别名: (R)-(+)-1,3-Octanediol；(3R)-octane-1,3-diol
• CAS: 120727-18-6
• 化学式: C₈H₁₈O₂
• 分子量: 146.23
• InChiKey: DCTMXCOHGKSXIZ-MRVPVSSYSA-N

物化性质

• 沸点：
  255.6±8.0 °C(Predicted)
• 密度：
  0.937±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  10
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  丙酮 、 (R)-octane-1,3-diol 在 对甲苯磺酸 、 sodium sulfate 作用下， 以 乙醚 为溶剂， 生成 1,3-Dioxane, 2,2-dimethyl-4-pentyl, 4R
  参考文献：
  名称：

  Novel 1,3-Dioxanes from Apple Juice and Cider

  摘要：

  Extracts obtained by XAD solid-phase extraction of apple juice and cider were separated by liquid chromatography on silica gel. Several new 1,3-dioxanes including the known 2-methyl-4-pentyl-1,3-dioxane and 2-methyl-4-[2'(Z)-pentenyl]-1,3-dioxane, were identified in the nonpolar fractions by GC/MS analysis and confirmed by chemical synthesis. The enantioselective synthesis of the stereoisomers of the 1,3-dioxanes was performed using (R)- and (R,S)-actane-1,3-diol and (R)- and (R,S)-5(Z)-octene-1,3-diol as starting material. Comparison with the isolated products indicated that the natural products consisted of a mixture of (2S,4R) and (2R,4R) stereoisomers in the ratio of approximately 10:1, except for 1,3-dioxanes generated from acetone and 2-butanone. It is assumed that the 1,3-dioxanes are chemically formed in the apples and cider from the natural apple ingredients (R)-octane-1,3-diol, (R)-5(Z)-octene-1,3-diol, (3R,7R)- and (3R,7S)-octane-1,3,7-triol, and the appropriate aldehydes and ketones, which are produced either by the apples or by yeast during fermentation of the apple juice.

  DOI：

  10.1021/jf990714x
• 作为产物：
  描述：

  正戊基溴化镁 在 lithium aluminium tetrahydride 、 magnesium bromide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (R)-octane-1,3-diol
  参考文献：
  名称：

  More than a Protective Group:  Synthesis and Applications of a New Chiral Silane

  摘要：

  Enantiomerically pure (-)-(R)- and (+)-(S)-(1-methoxy-2,2,2-triphenylethyl)dimethylsilanes (MOTES-H) were synthesized from triphenylacetaidehyde in five synthetic steps and with 60% overall yield. MOTES-protected alpha- and beta-hydroxycarbonyl compounds were used in Grignard and Diels-Alder reactions in the presence of MgBr2 to afford addition products with 87-98% yield and selectivities of up to >120:1 dr. With this method, the pine beetle pheromone (-)-frontalin (67%, 98.5% ee) and naturally occurring (-)-(R)-octane-1,3-diol (90%, >99% ee) were synthesized.

  DOI：

  10.1021/ol071382h

文献信息

• Catalytic Enantioselective Peroxidation of α,β-Unsaturated Aldehydes for the Asymmetric Synthesis of Biologically Important Chiral Endoperoxides
  作者：Lin Hu、Xiaojie Lu、Li Deng

  DOI：10.1021/jacs.5b05345

  日期：2015.7.8

  features an unprecedented cyclization cascade of a chiral bis(epoxy)hydroperoxide. The new methodology and synthetic strategy established in this work should be applicable to the enantioselective synthesis of a broad range of chiral 1,2-dioxolanes and 1,2-dioxanes, thereby facilitating biological and medicinal chemistry studies of peroxy natural products.

  我们开发了一种前所未有的高度对映选择性催化过氧化烯醛。这一发展的关键是发现改变氢过氧化物的结构对有机催化不对称过氧化的对映选择性有显着影响。这种新的转化使得开发了一种对映选择性路线，通向抗癌天然产物 stolonoxide 家族所有成员共享的核心结构，即连接的反式-3,6-二取代-1,2-二恶烷和反式-2,5-二取代-四氢呋喃环系。我们的路线还具有前所未有的手性双（环氧）氢过氧化物环化级联。在这项工作中建立的新方法和合成策略应适用于广泛范围的手性 1,2-二氧戊环和 1,2-二氧六环的对映选择性合成，
• Liposome coated with polyhydroxyalkanoate and production method thereof
  申请人：——

  公开号：US20030113368A1

  公开（公告）日：2003-06-19

  To provide a structure that has both drug holding capability and sustained releasability a liposome and mechanical strength of polyhydroxyalkanoate, is excellent in holding capability for hydrophilic drugs and other water-soluble substances as well as liphophilic drugs and other hydrophobic substances, and is capable of controlling the sustained releasability. To coat with polyhydroxyalkanoate at least part of the outer wall of the liposome.

  为了提供既具有药物持有能力又具有持续释放能力的结构，可以使用磷脂体和聚羟基脂肪酸酯的机械强度，这种结构对于亲水性药物和其他水溶性物质以及亲脂性药物和其他疏水性物质的持有能力非常出色，并且可以控制持续释放能力。可以在磷脂体的外壳至少部分涂覆聚羟基脂肪酸酯。
• Covalently Immobilized 2‐Deoxyribose‐5‐phosphate Aldolase (DERA) for Biocatalysis in Flow: Utilization of the 3‐Hydroxyaldehyde Intermediate in Reaction Cascades
  作者：Julia Hindges née Bramski、Johannes Döbber、Marc R. Hayes、Thomas Classen、Martina Pohl、Jörg Pietruszka

  DOI：10.1002/cctc.202200390

  日期：2022.8.19

  DERA in Flow: Covalent enzyme immobilization enables reaction cascades to be carried out via the capture of a reactive intermediate species. The combination of continuous biocatalysis and classical chemical transformations both in flow and in batch is shown. Establishment of this reaction protocol allows access to interesting building blocks for natural product synthesis.

  流动中的DERA：共价酶固定化使反应级联能够通过捕获反应性中间物质来进行。显示了连续生物催化和流动和分批的经典化学转化的组合。该反应协议的建立允许访问用于天然产物合成的有趣构建块。
• Acutiphycin and 20,21-didehydroacutiphycin, new antineoplastic agents from the cyanophyte Oscillatoria acutissima
  作者：Joseph J. Barchi、Richard E. Moore、Gregory M. L. Patterson

  DOI：10.1021/ja00338a031

  日期：1984.12
• Structurally diverse glycoconjugated volatile compounds from Oxytropis falcata Bunge
  作者：Shanshan Wang、Xiaojing Zhang、Sheng Que、Hong Liang、Pengfei Tu、Qingying Zhang

  DOI：10.1016/j.phytol.2018.07.015

  日期：2018.10

  A phytochemical investigation on the whole plant of Oxytropis falcata Bunge yielded 16 glycoconjugated compounds with structurally diverse volatile aglycones but similar sugars. Of these, five were previously undescribed compounds with different volatile aglycones but same glucuronic acid (1 -> 2) glucosyl moiety, including three octanol glucuronic acid (1 -> 2) glucosides (1-3), one acyclic monoterpenoid glucuronic acid (1 -> 2) glucoside (4), and one 4-phenyl-butan-2-ol glucuronic acid (1 -> 2) glucoside (5), and 11 were biological related known glucoconjugated volatile compounds (6-16) isolated from genus Oxytropis for the first time. The structures of these compounds were determined by extensive spectroscopic analysis of MS, 1D and 2D NMR data. The absolute configurations of aglycones and sugar residues were assigned via enzymatic hydrolysis and subsequently comparison of the specific rotations. This is the first report of such structurally diverse glycoconjugated volatile compounds from O. falcata, which might be regarded as the precursor of free volatile compounds, and presents scientific evidences for better clarifying the volatile compositions of this medicinal plant and genus Oxytropis.