2-(2-propynyl)-3a,4,7,7a-tetrahydro-4,7-epoxy-1H-isoindole-1,3(2H)-dione | 1016984-64-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(2-propynyl)-3a,4,7,7a-tetrahydro-4,7-epoxy-1H-isoindole-1,3(2H)-dione
• 英文别名: 2-Prop-2-ynyl-3a,4,7,7a-tetrahydro-4,7-epoxyisoindole-1,3-dione；2-prop-2-ynyl-3a,4,7,7a-tetrahydro-4,7-epoxyisoindole-1,3-dione
• CAS: 1016984-64-7
• 化学式: C₁₁H₉NO₃
• 分子量: 203.197
• InChiKey: GTMSPGUSFAMFDI-UHFFFAOYSA-N

物化性质

• 沸点：
  417.7±45.0 °C(Predicted)
• 密度：
  1.394±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-propynyl)-3a,4,7,7a-tetrahydro-4,7-epoxy-1H-isoindole-1,3(2H)-dione 以 甲苯 为溶剂， 以95%的产率得到1-(2-丙炔-1-基)-1H-吡咯-2,5-二酮
  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：

  7-氧杂双环(2.2.1)庚-5-烯-2,3-二甲酰亚胺 、 3-溴丙炔 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以39%的产率得到2-(2-propynyl)-3a,4,7,7a-tetrahydro-4,7-epoxy-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  用于蛋白质组学应用的同位素编码马来酰亚胺亲和标签

  摘要：

  同位素编码的亲和标签 (ICAT) 是基于质谱的定量蛋白质组学的宝贵工具，特别是用于比较正常、应激和患病组织中的蛋白质（半胱氨酸残基）硫醇氧化状态。然而，在大多数商业 ICAT 中使用的碘乙酰胺亲电试剂具有较差的硫醇选择性和适度的加合物形成率，这可能导致虚假结果。因此，我们设计并合成了三种含有硫醇选择性N-烷基马来酰亚胺亲电试剂（同位素编码的马来酰亚胺亲和标签 = ICMAT）的 ICAT，并将它们评估为用于溶菌酶和肌肉蛋白质组比例分析的质谱探针。两个包含丁烯/D 8 的ICMAT 对-丁烯接头是有效的 MS 探针，但对于典型的蛋白质组学工作流程而言并不理想，因为带有这些标签的肽段通常不会与 HPLC 共流出。转换为亚苯基/ 13 C 6 -亚苯基接头解决了这个问题，同时不影响加合物形成的效率。

  DOI：

  10.1021/acs.bioconjchem.1c00206

文献信息

• Site-Specific Amphiphilic Magnetic Copolymer Nanoaggregates for Dual Imaging
  作者：Saikat Mukherjee、Himadri Dinda、Litesh Shashank、Ipsita Chakraborty、Rangeet Bhattacharyya、Jayasri Das Sarma、Raja Shunmugam

  DOI：10.1021/acs.macromol.5b01716

  日期：2015.10.13

  Molecular imaging along with combinations of imaging modalities can provide a thorough understanding of disease, in particular, tumors. Magnetic resonance imaging (MIRE) offers exceptional tissue contrast and resolution; whereas optical imaging provides high sensitivity. Hence a norbornene based copolymer (Nor-Cob-Py-Fol) is reported in this paper as a dual-imaging agent. Nor-Cob-Py-Fol having Co2+ complex, pyrene and poly(ethylene glycol) derived folate, have been synthesized using ring-opening metathesis polymerization (ROMP). All the monomers and polymers are characterized by H-1 NMR, IR, GPC, and TGA techniques. The morphology of the copolymer nanoaggregates has been evaluated with DLS, TEM, and SEM techniques. The functionalization of Co2+ to the polymer is monitored by FTIR, NMR, and C-13 NMR spectroscopy. Furthermore, the presence of Co2+ in the nanoaggregates is confirmed by the EDX (SEM) technique. To prove the MRI capabilities nature of copolymer nanoaggregates, NMR performed at room temperature. Cell viability studies suggest the biocompatibility nature of the copolymer. Flow cytometry as well as epifluoroscence microscope experiments clearly demonstrate the dual-imaging ability of the newly designed copolymer. The much higher relaxivity ratio (r(2)/r(1)) of the present method clearly establishes the superiority of our system as one of the best contrast agents known to the practitioners of magnetic resonance imaging.
• Isotope-Coded Maleimide Affinity Tags for Proteomics Applications
  作者：Adam P. Wdowiak、Marisa N. Duong、Rohan D. Joyce、Amber E. Boyatzis、Mark C. Walkey、Gareth L. Nealon、Peter G. Arthur、Matthew J. Piggott

  DOI：10.1021/acs.bioconjchem.1c00206

  日期：2021.8.18

  thiol-selective N-alkylmaleimide electrophiles (isotope-coded maleimide affinity tags = ICMATs) and assessed these as mass spectrometry probes for ratiometric analysis of lysozyme and muscle proteomes. Two ICMAT pairs containing butylene/D8-butylene linkers were effective MS probes, but not ideal for typical proteomics workflows, because peptides bearing these tags frequently did not coelute with HPLC. A switch

  同位素编码的亲和标签 (ICAT) 是基于质谱的定量蛋白质组学的宝贵工具，特别是用于比较正常、应激和患病组织中的蛋白质（半胱氨酸残基）硫醇氧化状态。然而，在大多数商业 ICAT 中使用的碘乙酰胺亲电试剂具有较差的硫醇选择性和适度的加合物形成率，这可能导致虚假结果。因此，我们设计并合成了三种含有硫醇选择性N-烷基马来酰亚胺亲电试剂（同位素编码的马来酰亚胺亲和标签 = ICMAT）的 ICAT，并将它们评估为用于溶菌酶和肌肉蛋白质组比例分析的质谱探针。两个包含丁烯/D 8 的ICMAT 对-丁烯接头是有效的 MS 探针，但对于典型的蛋白质组学工作流程而言并不理想，因为带有这些标签的肽段通常不会与 HPLC 共流出。转换为亚苯基/ 13 C 6 -亚苯基接头解决了这个问题，同时不影响加合物形成的效率。
• 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.