methyl (Z)-β-methoxyacrylate | 5739-81-1

• 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 (Z)-β-methoxyacrylate
• 英文别名: (Z)-methyl 3-(methoxy)acrylate；(Z)-methyl 3-methoxyacrylate；methyl (Z)-3-methoxyacrylate；3(E)-methoxy-acrylic acid methyl ester；methyl (Z)-methoxypropenate；cis-β-Methoxy-acrylsaeuremethylester；methyl (Z)-3-methoxyprop-2-enoate
• CAS: 5739-81-1
• 化学式: C₅H₈O₃
• 分子量: 116.117
• InChiKey: AUTCCPQKLPMHDN-ARJAWSKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2918990090

反应信息

• 作为反应物：
  描述：

  methyl (Z)-β-methoxyacrylate 在 碘 作用下， 以 环己烷 为溶剂， 生成 3-甲氧基丙烯酸甲酯
  参考文献：
  名称：

  Double bond isomerizations in unsaturated esters and enol ethers. I. Equilibrium studies in cyclic and acyclic systems

  摘要：

  DOI：

  10.1021/jo00835a036
• 作为产物：
  描述：

  3-甲氧基丙烯酸甲酯 在 碘 作用下， 以 环己烷 为溶剂， 生成 methyl (Z)-β-methoxyacrylate
  参考文献：
  名称：

  Double bond isomerizations in unsaturated esters and enol ethers. I. Equilibrium studies in cyclic and acyclic systems

  摘要：

  DOI：

  10.1021/jo00835a036

文献信息

• Photoiodocarboxylation of Activated C═C Double Bonds with CO₂ and Lithium Iodide
  作者：Rossella Mello、Juan Camilo Arango-Daza、Teresa Varea、María Elena González-Núñez

  DOI：10.1021/acs.joc.8b02162

  日期：2018.11.2

  The photolysis at 254 nm of lithium iodide and olefins 1 carrying an electron-withdrawing Z-substituent in CO2-saturated (1 bar) anhydrous acetonitrile at room temperature produces the atom efficient and transition metal-free photoiodocarboxylation of the C═C double bond. The reaction proceeds well for terminal olefins 1 to form the new C–I and C–C σ-bonds at the α and β-positions of the Z-substituent

  室温下，在CO 2饱和（1 bar）无水乙腈中，带有吸电子Z取代基的碘化锂和烯烃1在254 nm处发生光解，产生C efficientC双键无原子和无过渡金属的光碘羧化反应。末端烯烃1的反应进展顺利，分别在Z取代基的α和β位置形成新的C-1和C-Cσ键，并受到极性质子溶剂或添加剂的强烈抑制。实验结果表明，反应通道通过乙腈中的自由基阴离子[CO 2 •– ]，但在水性介质中涉及不同的中间体。CO的稳定离子四极和电子供体-受体相互作用2与碘化物阴离子在反应过程中起着至关重要的作用，因为它们允许CO 2渗透到乙腈中的阴离子的溶剂化壳中，而不是在水中。讨论了不同条件下所涉及的反应路径和反应中间体。
• Development of the Ireland−Claisen Rearrangement of Alkoxy- and Aryloxy-Substituted Allyl Glycinates
  作者：James P. Tellam、David R. Carbery

  DOI：10.1021/jo1017124

  日期：2010.11.19

  The Ireland−Claisen rearrangement of 3-alkoxy- and 3-aryloxy-substituted allyl glycinates is presented. This [3,3]-sigmatropic rearrangement route offers direct access to syn β-alkoxy and β-aryloxy α-amino acid systems. In particular, N,N-diboc glycine esters rearrange with excellent diastereoselectivities (dr > 25:1). The synthesis of substrates, rearrangement optimization, and a discussion of stereoselection

  提出了3-烷氧基和3-芳氧基取代的烯丙基甘氨酸盐的爱尔兰-克莱森重排。该[3,3] -sigmatropic重排途径可直接进入顺式β-烷氧基和β-芳氧基α-氨基酸系统。特别地，N，N-二boc甘氨酸酯以优异的非对映选择性（dr> 25：1）重新排列。介绍了底物的合成，重排优化和立体选择的讨论。
• Nucleophilic attack of 2-sulfinyl acrylates: A mild and general approach to sulfenic acid anions
  作者：Suneel P. Singh、Jennifer S. O'Donnell、Adrian L. Schwan

  DOI：10.1039/b917217c

  日期：——

  An increasing number of reactions of sulfenic acid anions are being demonstrated in the literature. As such, mild, general and reliable means for the generation of sulfenates are due. In the current paper, an addition/elimination of 2-sulfinyl acrylates using various nucleophiles is demonstrated and evaluated as a protocol for alkane- and arenesulfenate generation. Cyclohexanethiolate, methoxide and

  文献中已证明亚磺酸阴离子的反应越来越多。因此，应采用温和，通用和可靠的方法生成亚磺酸盐。在当前的论文中，使用各种亲核试剂证明了丙烯酸2-亚磺酰基酯的添加/消除作用，并作为生成链烷烃和芳烃磺酸盐的方法进行了评估。环己烷硫醇盐，甲醇盐和正丁基锂在反应中各有优点，硫醇盐是一种温和，选择性和有效的试剂，可从丙烯酸2-亚磺酰基酯中释放出亚硫酸盐。认识到每个亲核试剂的添加/消除的立体特异性，并且提供了对硫醇盐和甲醇盐的特异性的解释。
• Stereoselective Addition of Alcohol to Acetylenecarboxylate Catalyzed by Silver(I) Salt
  作者：Yasutaka Kataoka、Osamu Matsumoto、Kazuhide Tani

  DOI：10.1246/cl.1996.727

  日期：1996.9

  A silver(I) salt catalyzed the stereoselective trans addition of alcohol to dimethyl acetylenedicarboxylate smoothly under mild conditions to afford dimethyl methoxyfumarate in a quantitative yield.

  银 (I) 盐在温和条件下平稳地催化醇立体选择性反式加成到乙炔二甲酸二甲酯，以定量收率提供甲氧基富马酸二甲酯。
• Syntheses of Mixed-Metal Sulfide Cubane-Type Clusters with the Novel PdMo3S4 Core and Reactivities of the Unique Tetrahedral Pd Site Surrounded by Sulfide Ligands toward Alkenes, CO, tBuNC, and Alkynes
  作者：Takashi Murata、Yasushi Mizobe、Hong Gao、Youichi Ishii、Takanori Wakabayashi、Fumio Nakano、Tomoaki Tanase、Shigenobu Yano、Masanobu Hidai、Izumi Echizen、Hiroshi Nanikawa、Shigeyuki Motomura

  DOI：10.1021/ja00087a025

  日期：1994.4.1

  An incomplete cubane-type cluster [Mo3S4(H2O)(9)]Cl-4 (1) reacted with Pd black in aqueous HCl to give a mixed-metal cubane-type cluster [PdMo3S4(H2O)(9)Cl]Cl-3 (2). Treatment of 2 with 3.3 equiv of 1,4,7-triazacyclononane (tacn) afforded a well-defined single cubane-type cluster [PdMo3S4(tacn)(3)Cl]Cl-3 (3), while an anion metathesis of 2 by 4-toluenesulfonate (TsO) resulted in the formation of a double cubane-type cluster [Pd2Mo6S8(H2O)(18)] (OTs)(8) (4). Detailed structures of both 3 and 4 have been determined by X-ray crystallography. Crystal data for 3.4H(2)O: orthorhombic, space group P2(1)2(1)2(1), a = 17.549(3) Angstrom, b = 20.032(4) Angstrom, c = 10.256(2) Angstrom, V = 3605 Angstrom(3), Z = 4, and R (R(w)) = 0.051 (0.062) for 4014 reflections. For 4.24H(2)O: triclinic, space group P1, a = 15.799(4) Angstrom, b = 18.079(6) Angstrom, c = 11.873(1) Angstrom, alpha = 108.75(2)degrees, beta = 108.73(1)degrees, gamma = 70.87(3)degrees, V = 2944 Angstrom(3), Z = 1, R (R(w)) = 0.028 (0.036) for 10 089 reflections. Cluster 3 was converted into a series of single cubane-type clusters [PdMo3S4(tacn)(3)(L)](4+) containing alkenes, CO, and (t)BuNC coordinated to the tetrahedral Pd site, by the initial anion exchange forming [PdMo3S4(tacn)(3)Cl]X(3) (8a, X = ClO4; 8b, X = BF4; 8c, X = PF6) followed by treatment with these molecules. The alkene cluster [PdMo3S4(tacn)(3)(cis-HOCH2CH=CHCH2OH)](ClO4)(4) (5a') and the carbonyl cluster [PdMo3S4(tacn)(3)(CO)]Cl(ClO4)(3) (6a) have been fully characterized by X-ray analyses. Crystal data for 5a'.2H(2)O: monoclinic, space group P2(1)/m, a = 12.314(1) Angstrom, b = 12.732(2) Angstrom, c = 15.736(2) Angstrom, beta = 94.01(1)degrees, V = 2461 Angstrom(3), Z = 2, R (R(w)) = 0.068 (0.081) for 2743 reflections. For 6a.3H(2)O: orthorhombic, space group Pbca, a = 15.485(13) Angstrom, b = 23.900(6) Angstrom, c = 23.326(7) Angstrom, V = 8633 Angstrom(3), Z = 8, and R (R(w)) = 0.061 (0.069) for 7761 reflections. Interestingly, cluster 8c catalyzes the reaction of a series of alkynic acid esters R(2)C-CCOOR(1) with alcohols R(3)OH to give the trans addition products (Z)-(R(3)O)R(2)C=CHCOOR(1) (R(1) = Me, Et, (t)Bu, Ph, R(2) = H, R(3) = Me; R(1) = R(3) = Me, R(2) = COOMe, Me; R(1) = Ph, R(2) = Et, R(3) = Me; R(1) = Me, R(2) = H, R(3) = Et, PhCH(2)) with quite high selectivity under mild conditions with retention of the cluster core.