methyl (E)-3-acetoxyacrylate | 52168-58-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (E)-3-acetoxyacrylate
• 英文别名: methyl β-acetoxyacrylate；Fumarsaeure-dimethylester；3-acetoxyacrylic acid methyl ester；methyl (E)-3-acetyloxyprop-2-enoate
• CAS: 52168-58-8
• 化学式: C₆H₈O₄
• 分子量: 144.127
• InChiKey: MSQPGECJSAMXBT-ONEGZZNKSA-N

物化性质

• 沸点：
  174.8±23.0 °C(Predicted)
• 密度：
  1.124±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (E)-3-acetoxyacrylate 、 三乙胺 生成
  参考文献：
  名称：

  10.1039/c1968000180

  摘要：

  DOI：

  10.1039/c1968000180
• 作为产物：
  描述：

  溶剂黄146 、 丙炔酸甲酯 在 五羰基溴铼(I) 作用下， 以 甲苯 为溶剂， 反应 15.0h， 生成 methyl (E)-3-acetoxyacrylate 、 (Z)-3-Acetoxy-acrylic acid methyl ester
  参考文献：
  名称：

  Re(CO)₅Br-Catalyzed Addition of Carboxylic Acids to Terminal Alkynes:  A High Anti-Markovnikov and Recoverable Homogeneous Catalyst

  摘要：

  The addition of carboxylic acids to terminal alkynes is efficiently catalyzed by the early transition-metal complex Re(CO)(5)Br in toluene or n-heptane at 110 degreesC in an air atmosphere, affording the anti-Markovnikov adducts in good yields with high selectivity. In most cases, the reactions afford unusual Z-adduct predominantly. When n-heptane was used as solvent, Re(CO)(5)Br can be partly recovered from the reaction mixture.

  DOI：

  10.1021/jo049455n

文献信息

• Multicomponent Reactions for the Synthesis of Complex Piperidine Scaffolds
  作者：Wei Zhu、Marisa Mena、Eric Jnoff、Na Sun、Patrick Pasau、Léon Ghosez

  DOI：10.1002/anie.200806065

  日期：2009.7.27

  Creating diversity: Multicomponent reactions for the synthesis of complex piperidine scaffolds lead to high levels of skeletal, functional, and stereochemical diversity in an efficient way (see scheme, X=OR, NR2). Connecting the acid chloride component to the dienophile generates polycyclic piperidine scaffolds by an intramolecular Diels–Alder reaction of the in situ generated azadienes.

  创造多样性：用于合成复杂哌啶支架的多组分反应以有效的方式导致高水平的骨骼，功能和立体化学多样性（参见方案，X = OR，NR 2）。通过原位生成的氮杂二烯的分子内Diels-Alder反应，将酰氯成分与亲二烯体相连，生成多环哌啶骨架。
• Synthesis of<i>Aristotelia</i>-type alkaloids. Part VII. Syntheses of (±)-sorelline, (±)-serratenone, and (±)-aristotelin-19-one
  作者：Stefan Burkard、Hans-Jürg Borschberg

  DOI：10.1002/hlca.19910740204

  日期：1991.3.13

  terpinylamine derivative (±)-4 was cyclized in 51% yield to the 19-substituted hobartine derivative (±)-20 upon exposure to anhydrous HCOOH. This pivotal intermediate was further elaborated into the indole alkaloids (±)-serratenone ((±)-22) and (±)-sorelline ((±)-29). In the course of these investigations, a novel rearrangement was uncovered; a Lewis acid-catalyzed 1,3-migration of an arylsulfonyl group from

  通过将吲哚保护的2-（吲哚-3-基）乙醛（5）与萜品胺衍生物（±）-4缩合而获得的亚胺在暴露时以51％的产率环化为19-取代的霍巴汀衍生物（±）-20到无水HCOOH。该关键中间体被进一步精制为吲哚生物碱（±）-serratenone（（±）-22）和（±）-solineline（（±）-29）。在这些调查过程中，发现了一种新颖的重排；一个路易斯酸催化从吲哚N原子到苯环的芳基磺酰基的1,3-迁移。合成（±）-aristotelin-19-one（（±）-34）的光谱性质与马兜铃内酯截然不同，马兜铃内酯是最近提出的一种代谢产物，导致对后者的结构进行了修改。
• 3,4-Bismethylenecyclopentanone ethylene ketal: A useful diene for[6.5]ring systems: Application to a formal synthesis of gibberellic acid
  作者：Achille Barco、Simonetta Benetti、Alberto Casolari、Stefano Manfredini、Gian Piero Pollini、Eleonora Polo、Vinicio Zanirato

  DOI：10.1016/s0040-4020(01)89252-8

  日期：1989.1

  A convenient preparation of 3,4-bismethylenecyclopentanone ethylene ketal, a new valuable diene for Diels-Alder reaction, designed to produce functionalized [6.5] ring systems, is described. A formal synthesis of gibberellic acd GA3 using as starting materials two cycloadducts derived from the title compound demonstrates the value and the applicability of this methodology for the construction of functionalized

  描述了一种方便的制备3,4-双亚甲基环戊酮乙烯缩酮的方法，该缩酮是一种用于Diels-Alder反应的新型有价值的二烯，旨在生产功能化的[6.5]环系。使用两个衍生自标题化合物的环加合物作为起始原料，正式合成了赤霉素acd GA 3，证明了该方法的价值和对功能化氢化茚体系构建的适用性。
• Oxidative Cross-Coupling of Acrylates with Vinyl Carboxylates Catalyzed by a Pd(OAc)₂/HPMoV/O₂ System
  作者：Yuji Hatamoto、Satoshi Sakaguchi、Yasutaka Ishii

  DOI：10.1021/ol047971u

  日期：2004.11.1

  [GRAPHICS]Oxidative cross-coupling of acrylates with vinyl carboxylates was first successfully achieved by the use of a Pd(OAc)(2)/HPMoV/O-2 system in fair to good yields. For instance, the reaction of n-butyl acrylate with vinyl acetate in the presence of catalytic amounts of Pd(OAc)(2) and H(4)PMo(11)Vo(40)(.)nH(2)O under O-2 in acetic acid at 70 degreesC for 12 In afforded the corresponding cross-coupling product, n-butyl 5-(acetoxy)-2,4-pentadienoate, in 70% yield.
• BURKARD, STEFAN;BORSCHBERG, HANS-JURG, HELV. CHIM. ACTA., 74,(1991) N, C. 275-289
  作者：BURKARD, STEFAN、BORSCHBERG, HANS-JURG

  DOI：——

  日期：——