2-Methylnon-4-yn-3-yl acetate | 156838-64-1

• 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: 2-Methylnon-4-yn-3-yl acetate
• CAS: 156838-64-1
• 化学式: C₁₂H₂₀O₂
• 分子量: 196.29
• InChiKey: PJIVPYKDSHEVPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Methylnon-4-yn-3-yl acetate 在 Pd-BaSO₄ 喹啉 、 氢气 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 16.0h， 生成 (Z)-2-methyl-non-4-en-3-ol
  参考文献：
  名称：

  Stereoconvergent ‘one-pot’ tandem [2,3]-Wittig-anionic oxy-Cope rearrangement of acyclic bis-allylic ethers in the diastereoselective synthesis of substituted tetrahydropyrans

  摘要：

  来自“单锅”串联 [2,3]-Wittig-负离子氧-科普 (AOC) 重排反应的不饱和醇与碘在乙腈中发生卤素环化反应，生成具有高立体选择性的取代四氢呋喃。

  DOI：

  10.1039/c39940001469
• 作为产物：
  描述：

  1-己炔 在 4-二甲氨基吡啶 、 正丁基锂 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 生成 2-Methylnon-4-yn-3-yl acetate
  参考文献：
  名称：

  Stereoconvergent ‘one-pot’ tandem [2,3]-Wittig-anionic oxy-Cope rearrangement of acyclic bis-allylic ethers in the diastereoselective synthesis of substituted tetrahydropyrans

  摘要：

  来自“单锅”串联 [2,3]-Wittig-负离子氧-科普 (AOC) 重排反应的不饱和醇与碘在乙腈中发生卤素环化反应，生成具有高立体选择性的取代四氢呋喃。

  DOI：

  10.1039/c39940001469

文献信息

• A Highly Efficient Preparative Method of α-Ylidene-β-Diketones via Au^III-Catalyzed Acyl Migration of Propargylic Esters
  作者：Shaozhong Wang、Liming Zhang

  DOI：10.1021/ja062777j

  日期：2006.7.1

  A highly efficient synthesis of α-alkylidene or benzylidene-β-diketones from readily available propargylic esters has been developed. The proposed key transformation is a novel intramolecular acyl migration to nucleophilic AuIII−C(sp2) bonds. Noteworthy features of this method are its efficiency and stereoselectivity. The yields of this reaction were mostly close to quantitative, and high to excellent

  已经开发出一种从容易获得的炔丙酯高效合成 α-亚烷基或亚苄基-β-二酮的方法。所提出的关键转变是一种新型的分子内酰基迁移到亲核 AuIII-C(sp2) 键。这种方法的显着特点是其效率和立体选择性。该反应的产率大多接近定量，并且在二烯基 β-二酮的情况下观察到高到极好的立体选择性。
• Gold-Catalyzed Efficient Formation ofα,β-Unsaturated Ketones from Propargylic Acetates
  作者：Meng Yu、Guotao Li、Shaozhong Wang、Liming Zhang

  DOI：10.1002/adsc.200600579

  日期：2007.4.2

  An efficient gold-catalyzed method for the preparation of α,β-unsaturated ketones from propargylic acetates has been developed. Under mild reaction conditions, β-monosubstituted enones were formed mostly with excellent E-selectivity. β,β-Disubstituted enones can be prepared from propargylic acetates derived from ketones. The high efficiency and mild nature of this reaction render it a viable alternative

  已经开发了一种有效的金催化方法，用于从乙酸炔丙基酯制备α，β-不饱和酮。在温和的反应条件下，形成的β-单取代的烯酮大多具有优异的E-选择性。β，β-二取代的烯酮可以由衍生自酮的炔丙基乙酸酯制备。该反应的高效率和温和的性质使其成为合成α，β-不饱和酮的可行选择。
• Triazole-Gold-Promoted, Effective Synthesis of Enones from Propargylic Esters and Alcohols: A Catalyst Offering Chemoselectivity, Acidity and Ligand Economy
  作者：Dawei Wang、Yanwei Zhang、Alexandria Harris、Lekh Nath S. Gautam、Yunfeng Chen、Xiaodong Shi

  DOI：10.1002/adsc.201100314

  日期：2011.10

  (TA-Au) were revealed as the effective catalysts in promoting propargylic ester rearrangement and sequential allene hydration, giving the enones with excellent yields (up to 97% yields, 0.2% loading). The catalysts could also catalyze the more challenging Meyer–Schuster rearrangement (0.5% loading, up to 98% yields). The reported reaction confirmed TA-Au as a chemoselective catalyst in promoting alkyne activation

  揭示了空气，湿气和热稳定的1,2,3-三唑配位的金（I）配合物（TA-Au）作为促进炔丙基酯重排和顺序烯化水合的有效催化剂，使烯酮具有优异的收率（最高可达产率为97％，负载为0.2％）。催化剂还可以催化更具挑战性的Meyer-Schuster重排（0.5％的负载量，最高98％的产率）。报道的反应证实TA-Au是一种化学选择性催化剂，可高效促​​进炔烃活化并改善配体经济性。
• Trimethylsilyl Trifluoromethanesulfonate- Accelerated Addition of Catalytically Generated Zinc Acetylides to Aldehydes
  作者：C. Wade Downey、Brian D. Mahoney、Vincent R. Lipari

  DOI：10.1021/jo900102w

  日期：2009.4.3

  In the presence of TMSOTf, a wide variety of terminal acetylenes add rapidly and efficiently to aldehydes via a catalytically generated zinc acetylide. In the absence of TMSOTf, no reaction is observed under otherwise identical conditions.
• Gold-Catalyzed Homogeneous Oxidative Cross-Coupling Reactions
  作者：Guozhu Zhang、Yu Peng、Li Cui、Liming Zhang

  DOI：10.1002/anie.200900585

  日期：2009.4.14

  AbstractOxidizing gold? A gold(I)/gold(III) catalytic cycle is essential for the first oxidative cross‐coupling reaction in gold catalysis. By using Selectfluor for gold(I) oxidation, this chemistry reveals the synthetic potential of incorporating gold(I)/gold(III) catalytic cycles into contemporary gold chemistry and promises a new area of gold research by merging powerful gold catalysis and oxidative metal‐catalyzed cross‐coupling reactions.magnified image