2,4-Pentadienoic acid, 3-methyl-5-phenyl-, ethyl ester, (4E)- | 586354-79-2

• 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: 2,4-Pentadienoic acid, 3-methyl-5-phenyl-, ethyl ester, (4E)-
• 英文别名: ethyl 3-methyl-5-phenylpenta-2,4-dienoate
• CAS: 586354-79-2
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: RWEDNCPDJOWFEF-LYIXSAAJSA-N

物化性质

• 沸点：
  338.9±21.0 °C(Predicted)
• 密度：
  1.030±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2,4-Pentadienoic acid, 3-methyl-5-phenyl-, ethyl ester, (4E)- 在 4-二甲氨基吡啶 、 C₁₈H₂₆N₃⁽¹⁺⁾*C₂H₆BF₂^(1-) 、 水 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 36.0h， 生成 (R,E)-ethyl 1-benzamido-6-oxo-4-styryl-1,2,3,6-tetrahydropyridine-2-carboxylate
  参考文献：
  名称：

  Organocatalytic Enantioselective γ-Aminoalkylation of Unsaturated Ester: Access to Pipecolic Acid Derivatives

  摘要：

  The direct gamma-carbon functionalization of alpha,beta-unsaturated esters via N-Heterocyclic Carbene (NHC) catalysis is disclosed. This catalytically generated nucleophilic gamma-carbon undergoes highly enantioselective additions to hydrazones. The resulting delta-lactam products can be readily transformed to optically enriched pipecolic acid derivatives.

  DOI：

  10.1021/ol402358k
• 作为产物：
  描述：

  磷酰基乙酸三乙酯 、 苄叉丙酮 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 12.0h， 生成 2,4-Pentadienoic acid, 3-methyl-5-phenyl-, ethyl ester, (4E)-
  参考文献：
  名称：

  烯醛与三氟甲基酮的氧化γ-加成：通过路易斯酸/N-杂环卡宾协同催化控制对映选择性

  摘要：

  公开了在 N-杂环卡宾 (NHC) 催化下 enals 的氧化 γ-官能化以产生不饱和 δ-内酯。通过路易斯酸 [Sc(OTf)(3) 或组合 Sc(OTf)(3)/Mg(OTf)(2)] 和 NHC 协同催化，实现了涉及相对偏远的 enal γ-碳的对映选择性控制。

  DOI：

  10.1021/ja303618z

文献信息

• Dienolate Annulation Approach for Assembly of Densely Substituted Aromatic Architectures
  作者：Kevin A. Scott、Jeffrey R. Groch、Isaac Chogii、Michael D. Delost、Pradipta Das、Jon T. Njardarson

  DOI：10.1021/acs.joc.1c01211

  日期：2021.8.6

  anion-cascade union of an enoate and a conjugated imine affords cyclohexenone products, which are readily aromatized to phenols. By engaging the intermediate cyclohexenones with Grignard reagents, a facile addition/elimination proceeds yielding chiral cyclohexadienes, which are then aromatized. In a complementary approach, the cyclohexenone products are converted into enol triflates, which provides a gateway to

  报道了从简单的无环结构单元有效组装复杂的芳族结构。烯酸和共轭亚胺的阴离子-级联结合提供环己烯酮产物，其易于芳构化为苯酚。通过将中间体环己烯酮与格利雅试剂结合，可以轻松添加/消除产生手性环己二烯，然后将其芳构化。在一种互补的方法中，环己烯酮产物被转化为烯醇三氟甲磺酸酯，这为交叉偶联和芳构化步骤后的多种芳香结构提供了途径。
• Stereoselective synthesis of analogs of natural isoprenoids based on the reaction of alkyl 4-dialkoxyphosphoryl-3-methylbut-2-enoates with aldehydes in ionic liquids and in an imidazolium salt—benzene system
  作者：S. G. Zlotin、G. V. Kryshtal、G. M. Zhdankina、P. A. Belyakov、E. P. Serebryakov

  DOI：10.1023/b:rucb.0000035653.43049.35

  日期：2004.3

  Condensation of alkyl 4-dialkoxyphosphoryl-3-methylbut-2-enoates with a number of aldehydes under the Homer-Emmons reaction conditions in 1-butyl-3-methylimidazolium hexafluorophosphate and tetrafluoroborate and in 1-butyl-3-methylimidazolium bromide-benzene and 1-butyl-2,3-dimethylimidazolium hexafluorophosphate-benzene systems was studied. The E/Z-stereoisomer ratio of the olefination products for the reaction carried out in ionic liquids was 3 : 1, which corresponds to the values attained previously in the KOH-benzene-(Bu4NBr)-N-n (cat.) system. Quantum-chemical calculations were used to determine the averaged radii (r(0)) of the [(Bu4N)-N-n] and substituted imidazolium cations by means of the Gaussian 98 program package. The stereoselectivity of olefination in the KOH-PhH-phasetransfer catalyst system decreases with a decrease in the r(0) value for the catalyst cation. The possibility of recovery and reuse of ionic liquids is demonstrated.
• Catalytic ketone olefination with methyltrioxorhenium
  作者：Filipe M. Pedro、Sebastian Hirner、Fritz E. Kühn

  DOI：10.1016/j.tetlet.2005.09.045

  日期：2005.11

  Methyltrioxorhenium (MTO) catalyses the olefination of ketones with ethyl diazoacetate in the presence of triphenyl-phosphane. Unactivated ketones require the addition of 0.5 equiv of benzoic acid to achieve good yields, while trifluoromethyl ketones require no co-catalyst. The optimised system allows the olefination of aromatic, aliphatic, unsaturated, cyclic and trifluoromethyl ketones. (c) 2005 Elsevier Ltd. All rights reserved.
• A new synthesis of α,β-unsaturated carboxylic esters using dialkyltelluronium carbethoxymethylide
  作者：Atsuhiro Osuka、Yasuo Mori、Hirohito Shimizu、Hitomi Suzuki

  DOI：10.1016/s0040-4039(00)81992-9

  日期：1983.1