(E)-methyl 4-methoxy-4-phenyl-2-butenoate | 117993-76-7

• 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: (E)-methyl 4-methoxy-4-phenyl-2-butenoate
• 英文别名: methyl (E)-4-methoxy-4-phenylbut-2-enoate
• CAS: 117993-76-7
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: WIZDDEMKPVYLOF-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 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：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-methyl 4-methoxy-4-phenyl-2-butenoate 以98%的产率得到
  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：
• 作为产物：
  描述：

  2-甲氧基-2-苯乙醇 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 反应 0.58h， 生成 (E)-methyl 4-methoxy-4-phenyl-2-butenoate
  参考文献：
  名称：

  Reductive cleavage reaction of .gamma.-functionalized .alpha.,.beta.-unsaturated esters and halomethyls mediated with magnesium in methanol

  摘要：

  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.

  DOI：

  10.1021/jo00058a038

文献信息

• Catalytic conversion of (β,γ-unsaturated esters, amides and nitriles into γ-alkoxy or γ-hydroxy α,β-unsaturated derivatives induced by persulfate anion oxidation of diphenyl diselenide
  作者：Marcello Tiecco、Lorenzo Testaferri、Marco Tingoli、Luana Bagnoli、Claudio Santi

  DOI：10.1039/c39930000637

  日期：——

  The reaction of β,γ-unsaturated esters, amides and nitriles with catalytic amounts of diphenyl diselenide and an excess of ammonium persulfate in alcohols or in water affords γ-alkoxy or γ-hydroxy α,β- unsaturated derivatives, respectively, in good yields.

  在醇或水中，使用催化量的二苯基二硒醚和过量的过硫酸铵，β,γ-不饱和酯、酰胺和腈能够分别以良好产率得到γ-烷氧基或γ-羟基的α,β-不饱和衍生物。
• Mg(OMe)₂ promoted allylic isomerization of γ-hydroxy-α,β-alkenoic esters to synthesize γ-ketone esters
  作者：Luhao Lai、A-Ni Li、Jiawei Zhou、Yarong Guo、Li Lin、Wei Chen、Rui Wang

  DOI：10.1039/c7ob00131b

  日期：——

  This work concerns the Mg(OMe)2 promoted allylic isomerization of γ-hydroxy-α,β-alkenoic esters with TMEDA as an additive. The isomerization proceeded under mild conditions and afforded γ-keto esters in high yield (up to 96%) within 2 h. Both (Z)- and (E)-γ-hydroxy-α,β-alkenoic esters were tolerated under the reaction conditions. This transformation involves the in situ formation of a dienolate intermediate

  这项工作涉及以TMEDA作为添加剂的Mg（OMe）2促进的γ-羟基-α，β-链烯酸酯的烯丙基异构化。异构化在温和的条件下进行，并在2小时内以高收率（高达96％）提供了γ-酮酯。在反应条件下，（Z）-和（E）-γ-羟基-α，β-链烯酸酯均被耐受。该转化涉及从容易获得的γ-羟基-α，β-链烯酸酯原位形成二烯酸酯中间体。该原位生成的二烯醇酯可以与苯甲醛反应并经历一种实用，有用的串联烯丙基异构化-羟醛反应，得到更多官能的化合物。
• Electrochemical Generation and Catalytic Use of Selenium Electrophiles
  作者：Thomas Wirth、Osamu Niyomura、Matthew Cox

  DOI：10.1055/s-2005-923585

  日期：——

  The generation and use of selenium electrophiles in ­catalytic, electrochemically driven selenenylation-elimination sequences is described.

  介绍了在催化、电化学驱动的硒基化-消除序列中硒亲电体的生成和使用。
• The carbene complex route to donor-acceptor-substituted cyclopropanes
  作者：Anette Wienand、Hans-Ulrich Reissig

  DOI：10.1016/s0040-4039(00)86046-3

  日期：1988.1
• Davies, Huw M. L.; Yokota, Yasuno, Tetrahedron Letters, 2000, vol. 41, # 25, p. 4850 - 4854
  作者：Davies, Huw M. L.、Yokota, Yasuno

  DOI：——

  日期：——