(2E,4E)-5-Phenyl-penta-2,4-dienoic acid methyl ester | 420089-28-7

• 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: (2E,4E)-5-Phenyl-penta-2,4-dienoic acid methyl ester
• CAS: 420089-28-7
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: OXWQBUHCJNXFLV-IIWBTEQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.43
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  (2E,4E)-5-Phenyl-penta-2,4-dienoic acid methyl ester 在 lithium hydroxide 、 盐酸 作用下， 以 水 、 二乙二醇 为溶剂， 反应 0.25h， 以100%的产率得到5-phenylpenta-2,4-dienoic acid
  参考文献：
  名称：

  Polymer-Assisted Solution-Phase Synthesis Under Combined Ultrasound and Microwave Irradiation: Preparation of α,β-Unsaturated Esters and Carboxylic Acids, Key Intermediates of Novel Sigma Ligands

  摘要：

  The optimal conditions to prepare ,-unsaturated methyl esters via Wittig reaction combining polymer-assisted solution-phase synthesis (PASPS) methodology and simultaneous ultrasound and microwave irradiation were established. The effects of temperature, solvent, and irradiation time were discussed. Results clearly indicated the superiority of combined ultrasound and microwave-assisted procedure over microwave-assisted methodology. Moreover, an efficient PASPS procedure to prepare ,-unsaturated carboxylic acids via tandem Wittig olefination and hydrolysis reaction was developed under combined ultrasound and microwave irradiation. Generally, a good conversion of aldehydes to acids was observed. The optimized protocols allowed us to quickly prepare a small collection of either ,-unsaturated esters or carboxylic acids, key intermediates for the drug-discovery process of new sigma ligands.

  DOI：

  10.1080/00397910902738112
• 作为产物：
  描述：

  methyl (E)-2-acetyl-5-phenylpent-4-enoate 在 [Rh2(O2CCPh3)4] 、 4-乙酰氨基苯磺酰叠氮 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 (2E,4E)-5-Phenyl-penta-2,4-dienoic acid methyl ester
  参考文献：
  名称：

  对映选择性合成2-芳基双环[1.1.0]丁烷羧酸酯

  摘要：

  的铑催化的反应2-重氮-5- arylpent -4- enoates可以通过催化剂和催化剂负载的适当选择被控制以形成任一2-芳基双环[1.1.0]丁烷羧酸或环己烯衍生物。两种产物都以高度非对映选择性的方式生产，其中2-芳基双环[1.1.0]丁烷羧酸酯在低催化剂负载下优先形成。当反应被Rh 2（R -BTPCP）4催化时，生成的2-芳基双环[1.1.0]丁烷羧酸盐具有很高的不对称诱导度（70-94％ee）。

  DOI：

  10.1021/ol303217s

文献信息

• Sequential cross-metathesis/phosphorus-based olefination: stereoselective synthesis of 2,4-dienoates
  作者：Tapas Paul、Rodrigo B. Andrade

  DOI：10.1016/j.tetlet.2007.06.031

  日期：2007.7

  A variety of stereodefined 2,4-dienoates have been prepared in a stereoselective manner by sequencing olefin cross-metathesis (CM) with phosphorus-based olefination reactions (Wittig and Horner–Wadsworth–Emmons) in good yield using commercially available reagents.

  通过使用可购得的试剂，以磷基烯烃化反应（Wittig和Horner-Wadsworth-Emmons）对烯烃交叉复分解（CM）进行测序，以立体选择性的方式制备了各种立体定义的2,4-二烯酸酯。
• A new method for carbon-carbon double bond formation promoted by tri-n-butylphosphine and zinc
  作者：Yanchang Shen、Yuankang Xin、Jianhua Zhao

  DOI：10.1016/s0040-4039(00)82281-9

  日期：——

  A new method for the carbon-carbon double bond formation by the reaction of aldehydes with methyl bromoacetate promoted by tri-n-butylphosphine and zinc has been described.

  已经描述了通过醛与由三正丁基膦和锌促进的溴乙酸甲酯反应形成碳-碳双键的新方法。
• Water is an efficient medium for Wittig reactions employing stabilized ylides and aldehydes
  作者：Jesse Dambacher、Wen Zhao、Amer El-Batta、Robert Anness、Changchun Jiang、Mikael Bergdahl

  DOI：10.1016/j.tetlet.2005.04.105

  日期：2005.6

  Water is demonstrated to be an excellent medium for the Wittig reaction employing stabilized ylides and aldehydes. Although the solubility in water appears to be an unimportant characteristic in achieving good chemical yields and E/Z-ratios, the rate of Wittig reactions in water is unexpectedly accelerated.

  事实证明，水是采用稳定化的丙烯化物和醛类进行维蒂希反应的极佳介质。尽管在水中的溶解度对于获得良好的化学收率和E / Z-比值似乎不是重要的特征，但是水中的维蒂希反应速率却出乎意料地加快了。
• Chiral Magnesium(II) Binaphtholates as Cooperative Brønsted/Lewis Acid-Base Catalysts for the Highly Enantioselective Addition of Phosphorus Nucleophiles to α,β-Unsaturated Esters and Ketones
  作者：Manabu Hatano、Takahiro Horibe、Kazuaki Ishihara

  DOI：10.1002/anie.201300938

  日期：2013.4.22

  cooperative Brønsted/Lewis acid–base supramolecular catalysts formed in situ from simple chiral magnesium(II) binaphtholate aqua complexes promoted the highly enantioselective 1,4‐hydrophosphinylation of α,β‐unsaturated esters with diaryl phosphine oxides and 1,2‐hydrophosphonylation of α,β‐unsaturated ketones with dialkyl phosphites (see scheme).

  一点点合作就可以走很长一段路：由简单的手性镁（II）二萘甲酸酯水配合物原位形成的Brønsted/ Lewis酸碱超分子合作催化剂促进了α，β-不饱和酯与二芳基膦的高度对映选择性1，，4-氢膦化。 α，β-不饱和酮的三价氧化物和1,2-氢膦酰基化与亚磷酸二烷基酯（参见方案）。
• A STUDY ON THE Z-SELECTIVE HORNER-WADSWORTH-EMMONS (HWE) REACTION OF METHYL DIARYLPHOSPHONOACETATES
  作者：Keisuke Kokin、Ken-Ichro Iitake、Yutaka Takaguchi、Hiromu Aoyama、Sadao Hayashi、Jiro Motoyoshiya

  DOI：10.1080/10426509808032451

  日期：1998.1

  aromatic and aliphatic aldehydes. While the phosphonoacetate (3) with bis(2,4-difluorophenyl)phosphono group showed the highest Z-selectivity in all reaction conditions employed, decrease of the selectivity was observed in the case of some phosphonoacetates with diarylphosphono groups. These experimental results and the theoretical studies calculated by AM1 or 3-21G* ab initio methods suggested that

  摘要 进行了实验和理论研究，以探索采用几种二芳基膦酰乙酸甲酯（3、4、5 和 6）和醛的 Homer-Wadsworth-Emmons (HWE) 反应中的 Z 选择性。Z-选择性取决于反应条件，例如碱、反应温度和磷原子上的芳香族取代基，但本研究中使用的几乎膦酰基乙酸酯在与芳香族和脂肪族醛的反应中都表现出 Z-选择性。虽然具有双(2,4-二氟苯基)膦酰基的膦酰基乙酸酯(3)在所采用的所有反应条件中显示出最高的Z-选择性，但在某些具有二芳基膦酰基的膦酰基乙酸酯的情况下观察到选择性降低。这些实验结果和通过 AM1 或 3-21G* ab initio 方法计算的理论研究表明，加成步骤过渡态中的空间效应比电子效应更重要。重新...的不同方面