2-allyl-3a,4,7,7a-tetrahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione | 32620-89-6

• 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-allyl-3a,4,7,7a-tetrahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione
• 英文别名: 2-prop-2-enyl-3a,4,7,7a-tetrahydro-4,7-epoxyisoindole-1,3-dione
• CAS: 32620-89-6
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: NITHXOHEXGCRMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  15
• 可旋转键数：
  2
• 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-allyl-3a,4,7,7a-tetrahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione 以 甲苯 为溶剂， 以97%的产率得到N-烯丙基马来酰亚胺
  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：

  sodium;3a,4,7,7a-tetrahydro-4,7-epoxyisoindol-2-ide-1,3-dione 以78%的产率得到
  参考文献：
  名称：

  KUROSAKI, T.;MATSUMOTO, T.;SAWADA, K.;KURISHIMA, S.;NUMAKURA, T., J. PHOTOGR. SCI., 36,(1988) N 3, C. 122-124

  摘要：

  DOI：

文献信息

• KUROSAKI, T.;MATSUMOTO, T.;SAWADA, K.;KURISHIMA, S.;NUMAKURA, T., J. PHOTOGR. SCI., 36,(1988) N 3, C. 122-124
  作者：KUROSAKI, T.、MATSUMOTO, T.、SAWADA, K.、KURISHIMA, S.、NUMAKURA, T.

  DOI：——

  日期：——
• [EN] THIOL COMPOUND, METHOD FOR SYNTHESIZING SAME, AND USES FOR SAID THIOL COMPOUND<br/>[FR] COMPOSÉ THIOL, PROCÉDÉ DE SYNTHÈSE DE CELUI-CI, ET UTILISATIONS DUDIT COMPOSÉ THIOL<br/>[JA] チオール化合物、その合成方法および該チオール化合物の利用
  申请人：SHIKOKU CHEM

  公开号：WO2020145111A1

  公开（公告）日：2020-07-16

  本発明は、新規なチオール化合物、該チオール化合物の合成方法、該チオール化合物を含有する硬化剤、該チオール化合物とエポキシ化合物を含有する樹脂組成物および、該チオール化合物と分子内に炭素－炭素二重結合を有するエン化合物を含有する樹脂組成物を提供することを目的とする。本発明のチオール化合物は、下記の化合物に例示される如く、ある種のジアルケン化合物とチオール化合物との反応生成物であって、分子内に２つ以上のチオエーテル結合を有するが、エステル結合を有しないチオール化合物である。
• 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.