acrylic acid 1-vinyl-hexyl ester | 145655-32-9

• 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: acrylic acid 1-vinyl-hexyl ester
• 英文别名: Oct-1-en-3-yl prop-2-enoate
• CAS: 145655-32-9
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: UPUOIEDJWFZQLM-UHFFFAOYSA-N

物化性质

• 沸点：
  228.9±9.0 °C(Predicted)
• 密度：
  0.892±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  acrylic acid 1-vinyl-hexyl ester 在 C₃₅H₄₈Cl₂N₃ORu⁽¹⁺⁾*Cl^(1-) 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 生成 5-戊基-2(5H)-呋喃酮
  参考文献：
  名称：

  使用异氰酸酯清除剂从金属残渣中高效，经济地纯化烯烃复分解产物

  摘要：

  描述了一种在空气中非脱气，未蒸馏的乙酸乙酯中使用可商购的自清除钌催化剂的烯烃复分解的可持续方案。此外，提出了一种省时，经济，可扩展的去除钌残留物的方法。结果表明，即使在极富挑战性的情况下，用异氰酸酯清除剂处理后反应混合物，然后用酸处理，然后进行简单过滤，即可制得钌污染低于5 ppm的OM产品。最后，描述了具有快速有效纯化方案的望远镜RCM / Suzuki-Miyaura序列，用于同时从溶液中去除Ru和Pd残留物。

  DOI：

  10.1039/c7gc03324a
• 作为产物：
  描述：

  1-辛烯-3-醇 、 丙烯酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 acrylic acid 1-vinyl-hexyl ester
  参考文献：
  名称：

  Ruthenium Carbene Complexes with N,N‘-Bis(mesityl)imidazol-2-ylidene Ligands:  RCM Catalysts of Extended Scope

  摘要：

  The ruthenium carbene complexes 3a,b bearing imidazol-2-ylidene ligands constitute excellent precatalysts for ring-closing metathesis (RCM) reactions allowing the formation of tri- and tetrasubstituted cycloalkenes. They also apply to annulations that are beyond the scope of the standard Grubbs carbene 1 as well as to ring-closing reactions of acrylic acid derivatives even if the resulting alpha,beta-unsaturated lactones (or lactams) are tri- or tetrasubstituted. The reactivity of 3a was found to be highly dependent on the reaction medium: particularly high reaction rates are observed in toluene, although this solvent also leads to an increased tendency of the catalyst to isomerize the double bonds of the substrates.

  DOI：

  10.1021/jo9918504

文献信息

• Highly efficient and time economical purification of olefin metathesis products from metal residues using an isocyanide scavenger
  作者：Grzegorz Szczepaniak、Anna Ruszczyńska、Krzysztof Kosiński、Ewa Bulska、Karol Grela

  DOI：10.1039/c7gc03324a

  日期：——

  A sustainable protocol of olefin metathesis in non-degassed, undistilled ethyl acetate under air with commercially available self-scavenging ruthenium catalysts is described. Furthermore, a time economical, cost-effective and scalable method of removal of ruthenium residues is presented. Treatment of post-reaction mixtures with an isocyanide scavenger and then with acid followed by a simple filtration

  描述了一种在空气中非脱气，未蒸馏的乙酸乙酯中使用可商购的自清除钌催化剂的烯烃复分解的可持续方案。此外，提出了一种省时，经济，可扩展的去除钌残留物的方法。结果表明，即使在极富挑战性的情况下，用异氰酸酯清除剂处理后反应混合物，然后用酸处理，然后进行简单过滤，即可制得钌污染低于5 ppm的OM产品。最后，描述了具有快速有效纯化方案的望远镜RCM / Suzuki-Miyaura序列，用于同时从溶液中去除Ru和Pd残留物。
• Sequential 1,4-Addition and Ireland−Claisen Rearrangement Promoted by a Manganese−PbCl₂−Me₃SiCl System¹
  作者：Kazuhiko Takai、Takashi Ueda、Hiroya Kaihara、Yoichi Sunami、Toshio Moriwake

  DOI：10.1021/jo9618482

  日期：1996.1.1
• Utility of phosphonium-substituted ester enolates as synthetic intermediates. A novel trialkylphosphine-catalyzed [3,3] rearrangement of allylic acrylates
  作者：Takeshi Hanamoto、Yoshiyasu Baba、Junji Inanaga

  DOI：10.1021/jo00054a004

  日期：1993.1

  A novel Ireland-type [3,3] rearrangement which utilizes a catalytic amount of a trialkylphosphine with allylic acrylates has been developed as a synthetic entry into alpha-methylene-gamma,delta-unsaturated carboxylic acids.
• Large‐Scale Synthesis of a Niche Olefin Metathesis Catalyst Bearing an Unsymmetrical N‐Heterocyclic Carbene (NHC) Ligand and its Application in a Green Pharmaceutical Context
  作者：Tomasz Nienałtowski、Paweł Szczepanik、Paweł Małecki、Dorota Czajkowska‐Szczykowska、Stefan Czarnocki、Jolanta Pawłowska、Anna Kajetanowicz、Karol Grela

  DOI：10.1002/chem.202003830

  日期：2020.12

  large‐scale synthesis of known Ru olefin metathesis catalyst VII featuring an unsymmetrical N‐heterocyclic carbene (NHC) ligand with one 2,5‐diisopropylphenyl (DIPP) and one thiophenylmethylene N‐substituent is reported. The optimised procedure does not require column chromatography in any step and allows for preparation of up to 0.5 kg batches of the catalyst from simple precursors. The application profile

  据报道大规模合成了已知的钌烯烃复分解催化剂VII，该催化剂具有一个不对称的N-杂环卡宾（NHC）配体，其中有一个2,5-二异丙基苯基（DIPP）和一个硫代苯基亚甲基N取代基。优化的程序在任何步骤都不需要柱色谱，并且可以从简单的前体中制备多达0.5 kg批次的催化剂。在环保型碳酸二甲酯（DMC）中研究了所得催化剂的应用概况。虽然七在与缺乏电子的配偶的交叉复分解（CM）中显示出低效率，对于具有容易使C-C双键异构化的底物，其结果达到了良好至优异的结果。这包括具有药用化学意义的多功能底物，例如精神活性5F‐PB‐22和NM‐2201的类似物以及两种PDE5抑制剂西地那非和伐地那非。最后，在DMC中对Vardenafil衍生物进行了较大规模的闭环复分解（RCM），从而以高收率和低Ru污染水平（7.7 ppm）直接分离了预期的产物（23 g）。
• Ruthenium Carbene Complexes with <i>N</i>,<i>N</i>‘-Bis(mesityl)imidazol-2-ylidene Ligands:  RCM Catalysts of Extended Scope
  作者：Alois Fürstner、Oliver R. Thiel、Lutz Ackermann、Hans-Jörg Schanz、Steven P. Nolan

  DOI：10.1021/jo9918504

  日期：2000.4.1

  The ruthenium carbene complexes 3a,b bearing imidazol-2-ylidene ligands constitute excellent precatalysts for ring-closing metathesis (RCM) reactions allowing the formation of tri- and tetrasubstituted cycloalkenes. They also apply to annulations that are beyond the scope of the standard Grubbs carbene 1 as well as to ring-closing reactions of acrylic acid derivatives even if the resulting alpha,beta-unsaturated lactones (or lactams) are tri- or tetrasubstituted. The reactivity of 3a was found to be highly dependent on the reaction medium: particularly high reaction rates are observed in toluene, although this solvent also leads to an increased tendency of the catalyst to isomerize the double bonds of the substrates.