dimethyl (Z)-2-(4-chlorophenoxy)-2-butenedioate | 24355-81-5

• 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: dimethyl (Z)-2-(4-chlorophenoxy)-2-butenedioate
• 英文别名: α-(4-Chlorphenoxy)-fumarsaeuredimethylester；Dimethyl-4-chlorphenoxy-fumarat；dimethyl (Z)-2-(4-chlorophenoxy)but-2-enedioate
• CAS: 24355-81-5
• 化学式: C₁₂H₁₁ClO₅
• 分子量: 270.669
• InChiKey: GLIUCQPOUGIZES-YFHOEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl (Z)-2-(4-chlorophenoxy)-2-butenedioate 、 靛红 、 L-脯氨酸 以 乙醇 为溶剂， 以44%的产率得到2′-(4-chlorophenoxy)-1′,2′-bis(methoxycarbonyl)-1′,2′,5′,6′,7′,7a′-hexahydrospiro[indole-3,3′-pyrrolizin]-2(1H)-one
  参考文献：
  名称：

  Synthesis of Functionalized Pyrrolizidines/Pyrrolidines Incorporating a Spirooxindole Motif through [3+2] Cycloaddition

  摘要：

  Dimethyl 2-(aryloxy)fumarates and dimethyl 2-(alkyl- or arylthio)fumarates are shown to be efficient dipolarophiles in 1,3-dipolar cycloaddition reaction with azomethine ylides, which are generated by the reaction of isatin with the secondary amino acids proline or sarcosine. In these reactions, dimethyl 2-(alkyl- or arylthio)fumarates afforded spirooxindolopyrrolizidines or -pyrrolidines in high yields with excellent regioselectivities, while dimethyl 2-(aryloxy)fumarates produced mixtures of regioisomers. DFT calculations at the B3LYP/6-31G(d,p) level were consistent with the observed results. Tri- and tetracyclic compounds were obtained through regio- and stereoselective intramolecular cycloaddition of O-vinylic salicylaldehyde with secondary amino acids.

  DOI：

  10.1055/s-0033-1338492
• 作为产物：
  描述：

  对氯苯酚 、 丁炔二酸二甲酯 在 盐酸胍 作用下， 以 水 、 丙酮 为溶剂， 反应 2.0h， 以58%的产率得到dimethyl (Z)-2-(4-chlorophenoxy)-2-butenedioate
  参考文献：
  名称：

  An efficient and green approach for the synthesis of vinyl aryl ethers in the presence of guanidine hydrochloride

  摘要：

  开发了一种立体选择性的程序，通过在温和反应条件下直接耦合二烷基炔二酸酯和取代酚或萘醇来形成烯基芳醚键。采用盐酸胍作为新催化剂，水-丙酮作为绿色溶剂，二烷基炔二酸酯在室温下与取代酚或萘醇反应，产率良好到优秀。

  DOI：

  10.3906/kim-1002-24

文献信息

• Trimethylamine catalyzed stereoselective reaction between dimethyl acetylenedicarboxylate and phenols
  作者：Farough Nasiri、Bahareh Atashkar

  DOI：10.1007/s00706-008-0919-z

  日期：2008.10

  Stereoselective reaction of various substituted phenols with dimethyl acetylenedicarboxylate in the presence of a catalytic amount of aqueous trimethylamine solution in dichloromethane leads to dimethyl 2-phenoxymaleates in good to excellent yields under mild condition.

  在催化量的三甲胺水溶液在二氯甲烷中的存在下，各种取代的酚与乙炔二甲酸二甲酯的立体选择反应在温和的条件下以良好的产率产生了2-苯氧基马来酸二甲酯。
• An efficient and green approach for the synthesis of vinyl aryl ethers in the presence of guanidine hydrochloride
  作者：SEYED MOHAMMAD VAHDAT、ROBABEH BAHARFAR

  DOI：10.3906/kim-1002-24

  日期：——

  A stereoselective procedure for vinyl aryl ether bond formation by direct coupling of dialkyl acetylenedicarboxylates and substituted phenols or naphthols under mild reaction conditions has been developed. Using guanidine hydrochloride as a new catalyst and water-acetone as green solvent, dialkyl acetylenedicarboxylates were reacted with substituted phenols or naphthols in room temperature to produce vinyl aryl ethers in good to excellent yields.

  开发了一种立体选择性的程序，通过在温和反应条件下直接耦合二烷基炔二酸酯和取代酚或萘醇来形成烯基芳醚键。采用盐酸胍作为新催化剂，水-丙酮作为绿色溶剂，二烷基炔二酸酯在室温下与取代酚或萘醇反应，产率良好到优秀。
• Diastereoselective O-Vinylation of Phenols using DMAD under Mild Reaction Conditions
  作者：Ebrahim Kianmehr、Katayoun Tabatabai、Alireza Abbasi、Hamideh Shokouhi Mehr

  DOI：10.1080/00397910802219163

  日期：2008.7.24

  An efficient and straightforward pyridine-catalyzed method allowing selective O-vinylation of phenols with DMAD is reported. The reaction is diastereoselective and leads exclusively to (Z)-configuration in high yields.
• A green and rapid approach for the stereoselective vinylation of phenol, thiol and amine derivatives in water
  作者：Yaghoub Sarrafi、Marzieh Sadatshahabi、Kamal Alimohammadi、Mahmood Tajbakhsh

  DOI：10.1039/c1gc15625j

  日期：——

  The stereoselective formation of C–O, C–S and C–N bonds by the reaction of phenols, thiols and amines with activated alkynes is described. The reactions are successfully conducted in water with excellent yields at room temperature. The lack of organic solvent use in the work-up procedure, the short reaction time and the environmentally benign mild reaction conditions are advantages of this method.

  通过酚、硫醇和胺与活化炔烃的反应，实现了C−O、C−S和C−N键的选择性立体形成。这些反应在室温下水相中以优异的产率成功进行。该方法的优势在于后处理过程中无需使用有机溶剂、反应时间短以及温和的环境友好型反应条件。
• Synthesis of Functionalized Pyrrolizidines/Pyrrolidines Incorporating a Spirooxindole Motif through [3+2] Cycloaddition
  作者：Yaghoub Sarrafi、Marzieh Sadatshahabi、Mahshid Hamzehloueian、Kamal Alimohammadi、Mahgol Tajbakhsh

  DOI：10.1055/s-0033-1338492

  日期：——

  Dimethyl 2-(aryloxy)fumarates and dimethyl 2-(alkyl- or arylthio)fumarates are shown to be efficient dipolarophiles in 1,3-dipolar cycloaddition reaction with azomethine ylides, which are generated by the reaction of isatin with the secondary amino acids proline or sarcosine. In these reactions, dimethyl 2-(alkyl- or arylthio)fumarates afforded spirooxindolopyrrolizidines or -pyrrolidines in high yields with excellent regioselectivities, while dimethyl 2-(aryloxy)fumarates produced mixtures of regioisomers. DFT calculations at the B3LYP/6-31G(d,p) level were consistent with the observed results. Tri- and tetracyclic compounds were obtained through regio- and stereoselective intramolecular cycloaddition of O-vinylic salicylaldehyde with secondary amino acids.