Benzoic acid (E)-1-methyl-but-2-enyl ester | 168919-17-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Benzoic acid (E)-1-methyl-but-2-enyl ester
• 英文别名: [(E)-pent-3-en-2-yl] benzoate
• CAS: 168919-17-3
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: JIOBIAWUJGIJKY-XVNBXDOJSA-N

物化性质

• 沸点：
  274.8±9.0 °C(Predicted)
• 密度：
  1.015±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  异氰基乙酸乙酯 、 Benzoic acid (E)-1-methyl-but-2-enyl ester 在 bis(η3-allyl-μ-chloropalladium(II)) caesium carbonate 、 1,2-双(二苯基膦)乙烷 作用下， 以 四氢呋喃 为溶剂， 以53%的产率得到(E)-2-Isocyano-3-methyl-hex-4-enoic acid ethyl ester
  参考文献：
  名称：

  An Improved Protocol for the Synthesis of Allylated Isonitriles

  摘要：

  α-异氰基醋酸盐可以作为适合的亲核试剂用于钯催化的烯丙基烷基化，生成α-烯丙基异腈。如果使用Cs2CO3作为碱来去质子化异腈，并在钯上使用dppe作为配体，则能获得最佳结果，这样可以抑制活性钯复合物的分解。

  DOI：

  10.1055/s-2004-834829
• 作为产物：
  描述：

  反-1,3-戊二烯 、 苯甲酸 在 磷酸 作用下， 生成 Benzoic acid (E)-1-methyl-but-2-enyl ester
  参考文献：
  名称：

  Acid-catalyzed alkenylation of aromatic compounds with 1,3-pentadiene as a route to new modifying additives for polymer compounds

  摘要：

  Alkenylation of a series of aromatic compounds with 1,3-pentadiene was studied. The oligomeric alkenylation products cured with hexamethylenetetramine were used for modifying elastic-strength properties of elastomeric compounds and improving the compatibility of the elastomers with silicic acid fillers.

  DOI：

  10.1134/s107042720808020x

文献信息

• PROCESS FOR THE SYNTHESIS OF KETONES FROM INTERNAL ALKENES
  申请人：CALIFORNIA INSTITUTE OF TECHNOLOGY

  公开号：US20140194604A1

  公开（公告）日：2014-07-10

  The present invention is directed to methods for oxidizing internal olefins to ketones. In various embodiments, each method comprising contacting an organic substrate, having an initial internal olefin, with a mixture of (a) a biscationic palladium salt; and (b) an oxidizing agent; dissolved or dispersed in a solvent system to form a reaction mixture, said solvent system comprising at least one C 2-6 carbon nitrile and optionally at least one secondary alkyl amide, said method conducted under conditions sufficient to convert at least 50 mol % of the initial internal olefin to a ketone, said ketone positioned on a carbon of the initial internal olefin. The transformation occurs at room temperature and shows wide substrate scope. Applications to the oxidation of seed oil derivatives and a bioactive natural product are described.

  本发明涉及将内烯烃氧化为酮的方法。在各种实施方式中，每种方法包括将具有初始内烯烃的有机底物与（a）双阳离子钯盐的混合物；和（b）氧化剂接触，溶解或分散在溶剂体系中形成反应混合物，所述溶剂体系包括至少一种C2-6碳腈和可选地至少一种次烷基酰胺，所述方法在足以将初始内烯烃的至少50摩尔％转化为酮的条件下进行，所述酮位于初始内烯烃的碳上。该转化在室温下发生，并显示出广泛的底物范围。描述了将其应用于种子油衍生物和生物活性天然产物的氧化。
• Mechanistic insight into copper-catalysed allylic substitutions with bis(triorganosilyl) zincs. Enantiospecific preparation of α-chiral silanes
  作者：Eric S. Schmidtmann、Martin Oestreich

  DOI：10.1039/b606589a

  日期：——

  Isotopic desymmetrisation, as well as (stereo)chemical correlation, has illuminated significant aspects of the σ–π–σ mechanism of copper-catalysed allylic substitution reactions: an enantiospecific and regioselective access to α-chiral silanes is presented.

  同位素不对称以及（立体）化学相关性揭示了铜催化烯丙基取代反应的ÏâÏâÏ机制的重要方面：介绍了一种获得δ-手性硅烷的对映体特异性和区域选择性方法。
• Kinetic Resolution and Unusual Regioselectivity in Palladium-Catalyzed Allylic Alkylations with a Chiral P,S Ligand
  作者：J. W. Faller、Jeremy C. Wilt、Jonathan Parr

  DOI：10.1021/ol0497382

  日期：2004.4.1

  Effective kinetic resolutions of acyclic allylic acetates and benzoates have been obtained using a palladium/(S)-BINAP(S) catalyst system. Unusually large preferences for the formation of branched alkylation products from 3-but-2-enyl and crotyl substrates have been observed.
• Tamaru, Yoshinao; Tanaka, Akihiro; Yasui, Kengo, Angewandte Chemie, 1995, vol. 107, # 7, p. 862 - 864
  作者：Tamaru, Yoshinao、Tanaka, Akihiro、Yasui, Kengo、Goto, Sachio、Tanaka, Shuji

  DOI：——

  日期：——
• Palladium-Catalyzed Equilibrium Addition of Acidic OH Groups across Dienes
  作者：Masaru Utsunomiya、Motoi Kawatsura、John F. Hartwig

  DOI：10.1002/anie.200352621

  日期：2003.12.8