(Z)-methyl 5-phenyl-3-pentenoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Z)-methyl 5-phenyl-3-pentenoate
• 英文别名: methyl (Z)-5-phenylpent-3-enoate
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: BZVFPQYPPWEUFD-WAYWQWQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  5
• 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

• 作为产物：
  描述：

  (Z)-methyl 4-(acetyloxy)-5-phenyl-2-pentenoate 生成 (Z)-methyl 5-phenyl-3-pentenoate
  参考文献：
  名称：

  Pak Chwang Siek, Lee Eun, Lee Ge Hyeong, J. Org. Chem, 58 (1993) N 6, S 1523-1530

  摘要：

  DOI：

文献信息

• Libraries for Receptor-Assisted Combinatorial Synthesis (RACS). The Olefin Metathesis Reaction
  作者：Thomas Giger、Maria Wigger、Stephan Audétat、Steven A. Benner

  DOI：10.1055/s-1998-1737

  日期：1998.6

  A library of alkenes is generated using the olefin metathesis reaction, and converted to a set of diols suitable for a receptor assisted combinatorial synthesis (RACS) experiment with borate as a linker.

  通过烯烃交叉反应生成了一系列烯烃库，并将其转化为一组适合于受体辅助组合合成（RACS）实验的二醇，硼酸盐作为连接体。
• Direct C–C Bond Formation of Allylic Alcohols with CO₂ toward Carboxylic Acids by Photoredox/Nickel Dual Catalysis
  作者：Zhengning Fan、Shenhao Chen、Song Zou、Chanjuan Xi

  DOI：10.1021/acscatal.2c00418

  日期：2022.3.4

  Carboxylation of allylic alcohols with carbon dioxide is accomplished by photoredox/nickel dual catalysis, generating linear acids exclusively with good Z/E stereoselectivity. Hantzsch ester is employed as the reductant instead of stoichiometric metallic reductants, and the reaction can be conducted under room temperature with a blue LED light source. Mechanistic studies reveal that the presence of

  烯丙醇与二氧化碳的羧基化是通过光氧化还原/镍双重催化完成的，仅生成具有良好Z/E立体选择性的线性酸。采用 Hantzsch 酯代替化学计量的金属还原剂作为还原剂，反应可以在室温下用蓝色 LED 光源进行。机理研究表明，该催化体系中水的存在对反应的成功至关重要，并且反应更有可能在原位形成的烯丙基碳酸氢盐的氧化加成中进行。
• Reductive cleavage reaction of .gamma.-functionalized .alpha.,.beta.-unsaturated esters and halomethyls mediated with magnesium in methanol
  作者：Chwang Siek Pak、Eun Lee、Ge Hyeong Lee

  DOI：10.1021/jo00058a038

  日期：1993.3

  Reductive cleavage of various types of C-O and C-N bonds tethered to alpha,beta-unsaturated esters and halomethyls was mediated with magnesium in methanol, which provided a facile method for the synthesis of delta-hydroxy or delta-amino beta,gamma-unsaturated esters and allylic alcohols. Regardless of the geometry (E or Z) of the alpha,beta-unsaturated esters, 1a-b, 5a-c, 11, 13, and 23, the cleavage product obtained was exclusively the E isomer of the corresponding deconjugated hydroxy and amino esters. The steric bias and ring strain of 15, 17, and 21 gave rise to a product mixture of E and Z isomers.