3-(1,3-dioxo-octahydroisoindol-2-yl)propionitrile | 192824-58-1

• 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: 3-(1,3-dioxo-octahydroisoindol-2-yl)propionitrile
• 英文别名: 3-[(3aR,7aS)-1,3-dioxo-3a,4,5,6,7,7a-hexahydroisoindol-2-yl]propanenitrile
• CAS: 192824-58-1；260435-04-9
• 化学式: C₁₁H₁₄N₂O₂
• 分子量: 206.244
• InChiKey: XNMPLBFMFBFORN-DTORHVGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  61.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(1,3-dioxo-octahydroisoindol-2-yl)propionitrile 在 chiral oxazaborolidine dimethyl sulfide borane 、 三氟化硼乙醚 、 臭氧 、 calcium chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 3.28h， 生成 3-[(1S,3aS,7aR)-1-(2-hydroxyethyl)-3-oxooctahydroisoindol-2-yl]propionitrile
  参考文献：
  名称：

  作为潜在手性催化剂的羟基取代的 DBN 型脒的对映选择性合成

  摘要：

  描述了 DBN 型的三个对映纯羟基取代脒的合成和 X 射线晶体结构。关键起始材料 5-(苯基磺酰基)pyrrolidin-2-one 是通过 oxazaborolidine 催化的内消旋酰亚胺还原去对称化获得的，并通过 N-acyliminium 离子化学进行功能化。通过臭氧分解或还原引入羟基。描述了在选定的迈克尔反应中使用羟基脒作为手性双功能催化剂的初步结果。

  DOI：

  10.1002/(sici)1099-0690(200001)2000:1<105::aid-ejoc105>3.0.co;2-n
• 作为产物：
  描述：

  3-氨基丙腈 、 1,2-cis-cyclohexanedicarboxylic anhydride 反应 0.5h， 以95%的产率得到3-(1,3-dioxo-octahydroisoindol-2-yl)propionitrile
  参考文献：
  名称：

  Oxazaborolidine catalysed enantioselective reduction of cyclic meso-imides

  摘要：

  Full details of the enantioselective reduction of cyclic meso-imides catalysed by an enantiopure oxazaborolidine derived from (S)-alpha,alpha-diphenylprolinol are reported. Treatment of the imides with borane in the presence of the catalyst led to a mixture of cis- and trans-hydroxylactams and, after subsequent ethanolysis, to the corresponding diastereomerically pure trans-ethoxylactams. The enantiomeric excesses were shown to be 68-94% by HPLC-determination. One example, in which the ethoxylactam was converted into the benzenesulfonyllactam, could be crystallized to >99% enantiomeric purity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00154-7

文献信息

• Oxazaborolidine catalysed enantioselective reduction of cyclic meso-imides
  作者：Martin Ostendorf、Romeo Romagnoli、Isabel Cabeza Pereiro、Eric C. Roos、Marinus J. Moolenaar、W.Nico Speckamp、Henk Hiemstra

  DOI：10.1016/s0957-4166(97)00154-7

  日期：1997.6

  Full details of the enantioselective reduction of cyclic meso-imides catalysed by an enantiopure oxazaborolidine derived from (S)-alpha,alpha-diphenylprolinol are reported. Treatment of the imides with borane in the presence of the catalyst led to a mixture of cis- and trans-hydroxylactams and, after subsequent ethanolysis, to the corresponding diastereomerically pure trans-ethoxylactams. The enantiomeric excesses were shown to be 68-94% by HPLC-determination. One example, in which the ethoxylactam was converted into the benzenesulfonyllactam, could be crystallized to >99% enantiomeric purity. (C) 1997 Elsevier Science Ltd.
• Enantioselective Synthesis of Hydroxy-Substituted DBN-Type Amidines as Potential Chiral Catalysts
  作者：Martin Ostendorf、Sandor van der Neut、Floris P. J. T. Rutjes、Henk Hiemstra

  DOI：10.1002/(sici)1099-0690(200001)2000:1<105::aid-ejoc105>3.0.co;2-n

  日期：2000.1

  The synthesis and X-ray crystal structures of three enantiopure hydroxy-substituted amidines of the DBN-type are described. The key starting material, a 5-(phenylsulfonyl)pyrrolidin-2-one, was obtained by an oxazaborolidine-catalysed reductive desymmetrization of a meso-imide and was functionalized through N-acyliminium ion chemistry. The hydroxy groups were introduced by ozonolysis or reduction. Preliminary

  描述了 DBN 型的三个对映纯羟基取代脒的合成和 X 射线晶体结构。关键起始材料 5-(苯基磺酰基)pyrrolidin-2-one 是通过 oxazaborolidine 催化的内消旋酰亚胺还原去对称化获得的，并通过 N-acyliminium 离子化学进行功能化。通过臭氧分解或还原引入羟基。描述了在选定的迈克尔反应中使用羟基脒作为手性双功能催化剂的初步结果。