dec-9-yn-5-ol | 55183-25-0

• 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: dec-9-yn-5-ol
• 英文别名: Dec-9-yn-5-ol
• CAS: 55183-25-0
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: OQPAXHXPOVOYOO-UHFFFAOYSA-N

物化性质

• 熔点：
  1.9°C (estimate)
• 沸点：
  247.64°C (rough estimate)
• 密度：
  0.8568 (estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  dec-9-yn-5-ol 在 三氧化硫吡啶 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以24%的产率得到9-decyn-5-one
  参考文献：
  名称：

  使用基于分子内氢胺化的反应序列合成吡啶和吡嗪

  摘要：

  管理问题！可以使用分子内加氢胺化/异构化/芳构化序列（参见方案）从简单的无环前体有效地获得各种吡啶和吡嗪。对甲苯磺酸（2摩尔％）用于催化这种新型炔烃环化反应，其中肟基允许随后的氧化还原中性芳构化步骤发生。

  DOI：

  10.1002/anie.200903922
• 作为产物：
  描述：

  5-己炔醛 、 正丁基氯化镁 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 dec-9-yn-5-ol
  参考文献：
  名称：

  Synthesis of Azomethine Imines Using an Intramolecular Alkyne Hydrohydrazination Approach

  摘要：

  Azomethine imines can be accessed upon heating appropriate alkynylhydrazide precursors. This simple thermal hydroamination approach allows the formation of five- and six-membered dipoles in modest to excellent yields. The structure of the acyl group is important to minimize side reactions and allow the isolation of the azomethine imines by column chromatography.

  DOI：

  10.1021/jo4011409

文献信息

• Reductive Cyclization of Unactivated Alkyl Chlorides with Tethered Alkenes under Visible‐Light Photoredox Catalysis
  作者：Miguel Claros、Felix Ungeheuer、Federico Franco、Vlad Martin‐Diaconescu、Alicia Casitas、Julio Lloret‐Fillol

  DOI：10.1002/anie.201812702

  日期：2019.4

  of unactivated alkyl chlorides with tethered alkenes. The cleavage of strong C(sp3)−Cl bonds is mediated by a highly nucleophilic low‐valent cobalt or nickel intermediate generated by visible‐light photoredox reduction employing a copper photosensitizer. The high basicity and multidentate nature of the ligands are key to obtaining efficient metal catalysts for the functionalization of unactivated alkyl

  大量市售的烷基氯的化学惰性阻碍了它们作为化学转化反应物的广泛应用。这项工作提出了一种金属光氧化还原方法，用于实现未活化的烷基氯与束缚烯烃的催化分子内还原环化。强C(sp 3 )−Cl键的断裂是由使用铜光敏剂的可见光光氧化还原还原产生的高度亲核的低价钴或镍中间体介导的。配体的高碱度和多齿性质是获得用于未活化的烷基氯官能化的有效金属催化剂的关键。
• A Gold-Catalyzed Cascade Reaction Involving an Unusual Intramolecular Redox Process
  作者：José Barluenga、Amadeo Fernández、Félix Rodríguez、Francisco J. Fañanás

  DOI：10.1002/chem.200901557

  日期：2009.8.17

  Gold catalysis: Secondary 5‐hexyn‐1‐ol derivatives react with indoles and other heteroaromatic compounds under gold‐catalyzed conditions to give the corresponding ketone derivative (see scheme) through a cascade reaction involving an initial intramolecular hydroalkoxylation reaction of the triple bond followed by an intermolecular hydroarylation reaction and an unusual intramolecular Oppenauer‐type

  金催化：在金催化的条件下，仲5-己炔-1-醇衍生物与吲哚和其他杂芳族化合物反应，通过级联反应（包括最初的三键分子内加氢烷氧基化反应，随后是级联反应）生成相应的酮衍生物（参见方案）分子间的氢芳基化反应和不寻常的分子内Oppenauer型氧化过程。
• Tandem Catalytic Indolization/Enantioconvergent Substitution of Alcohols by Borrowing Hydrogen to Access Tricyclic Indoles
  作者：Guoqiang Yang、Jiaoting Pan、Ya‐Ming Ke、Yongbing Liu、Yu Zhao

  DOI：10.1002/anie.202106514

  日期：2021.9.13

  An efficient tandem catalysis method is achieved for the direct conversion of alcohol-containing alkynyl anilines to valuable chiral 2,3-fused tricyclic indoles. This method relies on a tandem indolization followed by enantioconvergent substitution of alcohols via borrowing hydrogen to construct two rings in one step, enabled by relay and cooperative catalysis of a chiral iridium complex with a chiral

  实现了一种有效的串联催化方法，用于将含醇的炔基苯胺直接转化为有价值的手性 2,3-稠合三环吲哚。该方法依赖于串联吲哚化，然后通过借氢对醇进行对映收敛取代以一步构建两个环，通过手性铱配合物与手性磷酸的中继和协同催化实现。三环吲哚产物的高度非对映选择性转化也提供了对各种复杂多环二氢吲哚化合物的有效访问。
• A Practical Synthesis of Rosefuran. Furans from Acetylenes and Allyl Alcohols
  作者：Barry M. Trost、John A. Flygare

  DOI：10.1021/jo00084a026

  日期：1994.3

  A new atom-economical synthetic strategy for the synthesis of furans emerges from beta,gamma-unsaturated ketones which are readily available from acetylenes and allyl alcohols by simple additions in the presence of a ruthenium catalyst. Dihydroxylation using catalytic osmium tetraoxide creates a diol that is remarkably prone to cyclize to furans in the presence of an acid catalyst. The novelty of this synthesis lies in the overall strategy whereby furans are available in two steps from allyl alcohols and acetylenes with only water as the byproduct. A straightforward synthesis of the prized fragrance of oil of rose, rosefuran, from propargyl bromide, acetone, and 1-buten-3-ol in 23% overall yield illustrates the utility of this new strategy.
• Synthesis of Pyridines and Pyrazines Using an Intramolecular Hydroamination-Based Reaction Sequence
  作者：Toni Rizk、Eric J.-F. Bilodeau、André M. Beauchemin

  DOI：10.1002/anie.200903922

  日期：2009.10.19

  A management issue! Various pyridines and pyrazines can be efficiently accessed from simple acyclic precursors using an intramolecular hydroamination/isomerization/aromatization sequence (see scheme). p‐Toluenesulfonic acid (2 mol %) is used to catalyze this novel alkyne annulation, in which the oxime group allows for a subsequent redox‐neutral aromatization step to occur.

  管理问题！可以使用分子内加氢胺化/异构化/芳构化序列（参见方案）从简单的无环前体有效地获得各种吡啶和吡嗪。对甲苯磺酸（2摩尔％）用于催化这种新型炔烃环化反应，其中肟基允许随后的氧化还原中性芳构化步骤发生。