(R)-tert-butyl 2-[(S)-2,3-dihydro-1H-inden-1-ylcarbamothioyl]pyrrolidine-1-carboxylate | 1192235-68-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (R)-tert-butyl 2-[(S)-2,3-dihydro-1H-inden-1-ylcarbamothioyl]pyrrolidine-1-carboxylate
• CAS: 1192235-68-9
• 化学式: C₁₉H₂₆N₂O₂S
• 分子量: 346.494
• InChiKey: SPJPOJOMUUAZBO-JKSUJKDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  41.57
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-tert-butyl 2-[(S)-2,3-dihydro-1H-inden-1-ylcarbamothioyl]pyrrolidine-1-carboxylate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 以67%的产率得到(R)-N-[(S)-2,3-dihydro-1H-inden-1-yl]pyrrolidine-2-carbothioamide
  参考文献：
  名称：

  使用L-脯氨酰胺和L-脯氨酸硫酰胺作为有机催化剂的对映选择性分子间和分子内羟醛反应的水与无溶剂条件

  摘要：

  Abstractmagnified imageOrganocatalysts 1, derived from L‐proline and (1S,2R)‐cis‐1‐aminoindan‐2‐ol or (R)‐1‐aminoindane, are evaluated as promoters in the direct asymmetric aldol reaction between ketones and aromatic aldehydes in the presence of water and under solvent‐free reaction conditions. L‐Prolinethioamides 1c and 1d exhibited higher enantioselectivity than the corresponding prolinamides 1a and 1b in the model aldol reaction between cyclohexanone and 4‐nitrobenzaldehyde in the presence of 4‐nitrobenzoic acid as cocatalyst. In particular, L‐prolinethioamide 1d (5 mol%), derived from L‐proline and (R)‐1‐aminoindane, is shown as the most efficient organocatalyst studied promoting the direct aldol reaction of cycloalkyl, alkyl, and α‐functionalized ketones with aromatic aldehydes in the presence of water and under solvent‐free reaction conditions employing only 2 equivalents of nucleophile. Generally, anti‐aldol products are obtained in high yields and excellent diastereo‐ and enantioselectivities (up to >98/2 anti/syn, up to 98% ee). Solvent‐free conditions give slightly higher dr and ee than using water as solvent. In addition, organocatalyst 1d can be easily recovered by extractive work‐up and reused. Prolinethioamide 1d (5 mol%) in combination with 4‐NO2C6H4CO2H (5 mol%) is also a very effective organocatalytic system for the asymmetric solvent‐free intramolecular Hajos–Parrish–Eder–Sauer–Wiechert reaction with comparable or higher levels of enantioselectivity (up to 88% ee) to other reported catalysts in organic solvents.

  DOI：

  10.1002/adsc.200800814
• 作为产物：
  描述：

  (R)-tert-butyl 2-[(R)-2,3-dihydro-1H-inden-1-ylcarbamoyl]pyrrolidine-1-carboxylate 在 劳森试剂 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以66%的产率得到(R)-tert-butyl 2-[(S)-2,3-dihydro-1H-inden-1-ylcarbamothioyl]pyrrolidine-1-carboxylate
  参考文献：
  名称：

  使用L-脯氨酰胺和L-脯氨酸硫酰胺作为有机催化剂的对映选择性分子间和分子内羟醛反应的水与无溶剂条件

  摘要：

  Abstractmagnified imageOrganocatalysts 1, derived from L‐proline and (1S,2R)‐cis‐1‐aminoindan‐2‐ol or (R)‐1‐aminoindane, are evaluated as promoters in the direct asymmetric aldol reaction between ketones and aromatic aldehydes in the presence of water and under solvent‐free reaction conditions. L‐Prolinethioamides 1c and 1d exhibited higher enantioselectivity than the corresponding prolinamides 1a and 1b in the model aldol reaction between cyclohexanone and 4‐nitrobenzaldehyde in the presence of 4‐nitrobenzoic acid as cocatalyst. In particular, L‐prolinethioamide 1d (5 mol%), derived from L‐proline and (R)‐1‐aminoindane, is shown as the most efficient organocatalyst studied promoting the direct aldol reaction of cycloalkyl, alkyl, and α‐functionalized ketones with aromatic aldehydes in the presence of water and under solvent‐free reaction conditions employing only 2 equivalents of nucleophile. Generally, anti‐aldol products are obtained in high yields and excellent diastereo‐ and enantioselectivities (up to >98/2 anti/syn, up to 98% ee). Solvent‐free conditions give slightly higher dr and ee than using water as solvent. In addition, organocatalyst 1d can be easily recovered by extractive work‐up and reused. Prolinethioamide 1d (5 mol%) in combination with 4‐NO2C6H4CO2H (5 mol%) is also a very effective organocatalytic system for the asymmetric solvent‐free intramolecular Hajos–Parrish–Eder–Sauer–Wiechert reaction with comparable or higher levels of enantioselectivity (up to 88% ee) to other reported catalysts in organic solvents.

  DOI：

  10.1002/adsc.200800814