2-methylundec-1-en-3-yn-5-yl acetate | 1154612-40-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-methylundec-1-en-3-yn-5-yl acetate
• CAS: 1154612-40-4
• 化学式: C₁₄H₂₂O₂
• 分子量: 222.327
• InChiKey: ZCIAGJNRSKSKLK-UHFFFAOYSA-N

物化性质

• 沸点：
  296.0±23.0 °C(predicted)
• 密度：
  0.919±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 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-methylundec-1-en-3-yn-5-yl acetate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 1-(2-methyloxiran-2-yl)non-1-yn-3-yl acetate
  参考文献：
  名称：

  Silver(I)-Catalyzed Cascade: Direct Access to Furans from Alkynyloxiranes

  摘要：

  Functionalized furans are conveniently formed by a new silver(I)-catalyzed reaction of alk-1-ynyl oxiranes in the presence of p-toluenesulfonic acid and methanol. Evidence supported a cascade mechanism.

  DOI：

  10.1021/jo900483m
• 作为产物：
  描述：

  庚醛 、 2-甲基-1-丁烯-3-炔 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 8.5h， 生成 2-methylundec-1-en-3-yn-5-yl acetate
  参考文献：
  名称：

  无机-有机杂多酸-金（I）杂化物：结构和催化应用

  摘要：

  金（I）-polyoxometalate的杂交复合物1 - 4（[PPH 3 AuMeCN] X ħ 4- X硅钨酸12 ø 40，X = 1-4）的合成和表征。XRD，FTIR，31 P和29 Si幻角旋转（MAS）NMR，质谱和SEM-能量色散X射线完全确定了初级金（I）-多金属氧酸盐1（x = 1）的结构光谱学（EDX）技术。此外，在新的炔丙基重排中，该络合物与标准的均相金催化剂相比，具有更好的催化活性和选择性。宝石二酯。

  DOI：

  10.1002/chem.201304680

文献信息

• Gold-Catalyzed Cycloisomerization-Halogenation Sequence of 1,3-Enyne Esters with NXS: Efficient Synthesis of 5-Bromo/Iodo Cyclopentenones
  作者：Yuanyuan Zhou、Xianxiao Chen、Dongliang Yin、Yuan Ling、Shifa Wang、Xiaoxiang Zhang、Weidong Rao

  DOI：10.1002/ejoc.201801530

  日期：2019.2.7

  An efficient and regioselective protocol for the construction of 5‐bromo/iodo cyclopentenones from gold(I)‐catalyzed tandem cycloisomerization/electrophilic halogenation of 1,3‐enyne esters with NXS in a one‐pot two‐step operation has been developed. The synthetic utility was further demonstrated by the scale‐up preparation of one example followed by its conversion to the corresponding α‐substituted

  已经开发了一种高效且区域选择性的方案，该方案可通过金（I）催化的NXS在单锅两步操作中由金（I）催化的串联1,3-烯炔酯的串联环异构化/亲电子卤化反应构建5-溴/碘代环戊烯酮。通过放大制备一个实施例，然后将其转化为具有各种功能的相应α-取代的环戊烯酮，进一步证明了该合成实用性。
• Metal Confinement through <i>N</i> -(9-Alkyl)fluorenyl-Substituted N-Heterocyclic Carbenes and Its Consequences in Gold-Catalysed Reactions Involving Enynes
  作者：Matthieu Teci、Damien Hueber、Patrick Pale、Loïc Toupet、Aurélien Blanc、Eric Brenner、Dominique Matt

  DOI：10.1002/chem.201701129

  日期：2017.6.7

  gold(I) and gold(III) complexes containing bulky bis‐N,N′‐(9‐alkylfluorenyl) heterocyclic carbene (RF‐NHC) ligands have been prepared in high yields from appropriate imidazolinium, imidazolium and benzimidazolium salts. In all complexes, the carbene ligand provides high steric protection of the Au−X bond trans to the carbenic C atom. Irrespective of the metal oxidation state, the complexes showed high efficiency

  一系列的金（I）和含有双-笨重金（III）络合物Ñ，N' - （9-亚烷基芴）杂环卡宾（[R F-NHC）配体已在从适当的咪唑啉鎓，咪唑鎓和苯并咪唑盐高收率制备。在所有络合物中，卡宾配体都提供了对反位至碳原子C原子的Au-X键的高度空间保护。无论金属氧化态如何，络合物在乙酸乙炔酯的串联3,3重排/ Nazarov反应中均显示出高效率。一种Au III络合物，[AuCl 3（RF-NHC）]，进一步发现它适用于炔丙基羧酰胺的有效环化。此外，与相关的基于传统的大块N-杂环卡宾的NHC-gold（I）配合物（特别是1,3-双-（2,6-二异丙基苯基）咪唑-2-亚烷基（IPr），1,3-双（2,4,6-三甲基苯基）咪唑-2-亚基（IMes）和1,3-（双叔丁基）咪唑-2-亚基（I t Bu）），研究[Au I Cl（RF-NHC）]配合物在吲哚存在下催化1,6-烯炔转化为单一产物；这是由于配体的包
• Polyoxometalate-Gold(I)/H⁺ Complexes: Air-Stable, Efficient, Polyvalent, and Bifunctional Catalysts
  作者：Damien Hueber、Marie Hoffmann、Pierre de Frémont、Patrick Pale、Aurélien Blanc

  DOI：10.1021/acs.organomet.5b00656

  日期：2015.10.26

  Gold(I)/H+-polyoxometalate hybrids, with general formula [POM](x-)[H](x-1)(+)[R3PAu(MeCN)](+), were synthesized and fully characterized by P-31 and Si-29 MAS or liquid NMR, FT-IR, and mass spectroscopy. All these polyoxometalate gold(I) complexes exhibited excellent catalytic activity and selectivity compared to standard homogeneous gold catalysts in a large range of reactions. The variation of the ligand and the polyoxometalate nature around gold(I) also highlighted the flexibility and the multifunctionality of such catalysts, as well as their recyclability.
• Synthesis, Characterization, and Catalytic Activity of Cationic NHC Gold(III) Pyridine Complexes
  作者：Serena Orbisaglia、Béatrice Jacques、Pierre Braunstein、Damien Hueber、Patrick Pale、Aurélien Blanc、Pierre de Frémont

  DOI：10.1021/om400338k

  日期：2013.8.12

  A series of cationic gold(I/III) pyridine complexes of the type [(L)Au(pyr)](PF6) and [(L)AuCl2(pyr)](PF6), where L = IPr, (1, 5); L = IMes (2, 6); L = (IBu)-Bu-t, (3, 7); L = ICy (4, 8); and L = PPh3, (9, 10), were synthesized and characterized by NMR spectroscopy and single-crystal X-ray diffraction. The stability of the new complexes and their catalytic activity in five well-established organic transformations were assessed.
• Synthesis, Characterization, and Catalytic Activity of Alcohol-Functionalized NHC Gold(I/III) Complexes
  作者：Béatrice Jacques、Damien Hueber、Sophie Hameury、Pierre Braunstein、Patrick Pale、Aurélien Blanc、Pierre de Frémont

  DOI：10.1021/om500240h

  日期：2014.5.12

  A series of alcohol-functionalized NHC gold(I/III) complexes of the types [(L)Au(Cl or NTf2)] and [(L)AuCl3] (L = IPrEtOH, (1, 4, 5), IMesEtOH (2, 6), IMeEtOH (3, 7)) was readily synthesized and characterized by NMR spectroscopy and single-crystal X-ray diffraction. The catalytic activity of the new complexes was assessed and compared with that of other gold catalysts, in the tandem 3,3-rearrangement-Nazarov reactions of enynyl acetate and the rearrangement reaction of alkynyloxirane. The new complexes appeared to be dual-site catalysts in both transformations, thanks to the presence of the primary alcohol function tethered to the NHC ligands.