dimethyl (Z)-2-(2-naphthylthio)-2-butenedioate | 1350638-29-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: dimethyl (Z)-2-(2-naphthylthio)-2-butenedioate
• 英文别名: dimethyl (Z)-2-naphthalen-2-ylsulfanylbut-2-enedioate
• CAS: 1350638-29-7
• 化学式: C₁₆H₁₄O₄S
• 分子量: 302.351
• InChiKey: YLNXPCDTNPUMCM-UVTDQMKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  77.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl (Z)-2-(2-naphthylthio)-2-butenedioate 、 靛红 、 L-脯氨酸 以 乙醇 为溶剂， 以85%的产率得到1′,2′-bis(methoxycarbonyl)-2′-(2-naphthylthio)-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：

  丁炔二酸二甲酯 、 2-萘硫醇 在 水 、 potassium carbonate 作用下， 生成 dimethyl (Z)-2-(2-naphthylthio)-2-butenedioate
  参考文献：
  名称：

  A green and rapid approach for the stereoselective vinylation of phenol, thiol and amine derivatives in water

  摘要：

  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。

  DOI：

  10.1039/c1gc15625j

文献信息

• 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.