3-(2-Hydroxyethylsulfanyl)-1-prop-2-ynylpyrrolidine-2,5-dione | 1159842-72-4

• 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: 3-(2-Hydroxyethylsulfanyl)-1-prop-2-ynylpyrrolidine-2,5-dione
• 英文别名: 3-(2-hydroxyethylsulfanyl)-1-prop-2-ynylpyrrolidine-2,5-dione
• CAS: 1159842-72-4
• 化学式: C₉H₁₁NO₃S
• 分子量: 213.257
• InChiKey: BJSFGYOMNOVKCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  82.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-巯基丙酸甲酯 、 3-(2-Hydroxyethylsulfanyl)-1-prop-2-ynylpyrrolidine-2,5-dione 在 安息香双甲醚 作用下， 以 氯仿 为溶剂， 以97%的产率得到Methyl 3-[3-[3-(2-hydroxyethylsulfanyl)-2,5-dioxopyrrolidin-1-yl]-2-(3-methoxy-3-oxopropyl)sulfanylpropyl]sulfanylpropanoate
  参考文献：
  名称：

  Experimental and Theoretical Studies of Selective Thiol–Ene and Thiol–Yne Click Reactions Involving N-Substituted Maleimides

  摘要：

  A combination of experimental and computational methods has been used to understand the reactivity and selectivity of orthogonal thiol-ene and thiol-yne "click" reactions involving N-allyl maleimide (1) and N-propargyl maleimide (2). Representative thiols methyl-3-mercaptopropionate and beta-mercaptoethanol are shown to add exclusively and quantitatively to the electron poor maleimide alkene of 1 and 2 under base (Et3N) initiated thiol-Michael conditions. Subsequent radical-mediated thiol-ene or thiol-yne reactions can be carried out to further functionalize the remaining allyl or propargyl moieties in near quantitative yields (>95%). Selectivity, however, can only be achieved when base-initiated thiol-Michael reactions are carried out first, as radical-mediated reactions between equimolar amounts of thiol and N-substituted maleimides give complex mixtures of products. CBS-QB3 calculations have been used to investigate the energetics and kinetics of reactions between a representative thiol (methyl mercaptan) with N-allyl and N-propargyl maleimide under both base-initiated and radical-mediated conditions. Calculations help elucidate the factors that underlie the selective base-initiated and nonselective radical-mediated thiol-ene/yne reactions. The results provide additional insights into how to design selective radical-mediated thiol-ene/yne reactions.

  DOI：

  10.1021/jo4014436
• 作为产物：
  描述：

  3-[(Prop-2-yn-1-yl)carbamoyl]prop-2-enoic acid 以 aq. phosphate buffer 、 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 8.5h， 生成 3-(2-Hydroxyethylsulfanyl)-1-prop-2-ynylpyrrolidine-2,5-dione
  参考文献：
  名称：

  Bridging cells of three colors with two bio-orthogonal click reactions

  摘要：

  两种生物正交点击反应被用于成功连接三种颜色的原核生物E. coli或真核生物HEK 293T细胞。

  DOI：

  10.1039/c5sc01315a

文献信息

• Experimental and Theoretical Studies of Selective Thiol–Ene and Thiol–Yne Click Reactions Involving <i>N</i>-Substituted Maleimides
  作者：Robert M. Stolz、Brian H. Northrop

  DOI：10.1021/jo4014436

  日期：2013.8.16

  A combination of experimental and computational methods has been used to understand the reactivity and selectivity of orthogonal thiol-ene and thiol-yne "click" reactions involving N-allyl maleimide (1) and N-propargyl maleimide (2). Representative thiols methyl-3-mercaptopropionate and beta-mercaptoethanol are shown to add exclusively and quantitatively to the electron poor maleimide alkene of 1 and 2 under base (Et3N) initiated thiol-Michael conditions. Subsequent radical-mediated thiol-ene or thiol-yne reactions can be carried out to further functionalize the remaining allyl or propargyl moieties in near quantitative yields (>95%). Selectivity, however, can only be achieved when base-initiated thiol-Michael reactions are carried out first, as radical-mediated reactions between equimolar amounts of thiol and N-substituted maleimides give complex mixtures of products. CBS-QB3 calculations have been used to investigate the energetics and kinetics of reactions between a representative thiol (methyl mercaptan) with N-allyl and N-propargyl maleimide under both base-initiated and radical-mediated conditions. Calculations help elucidate the factors that underlie the selective base-initiated and nonselective radical-mediated thiol-ene/yne reactions. The results provide additional insights into how to design selective radical-mediated thiol-ene/yne reactions.
• Bridging cells of three colors with two bio-orthogonal click reactions
  作者：Yue Yuan、Di Li、Jia Zhang、Xianmin Chen、Chi Zhang、Zhanling Ding、Lin Wang、Xueqian Zhang、Junhua Yuan、Yinmei Li、Yanbiao Kang、Gaolin Liang

  DOI：10.1039/c5sc01315a

  日期：——

  Two bio-orthogonal click reactions were employed to bridge prokaryotic E. coli or eukaryotic HEK 293T cells of three colors successfully.

  两种生物正交点击反应被用于成功连接三种颜色的原核生物E. coli或真核生物HEK 293T细胞。