(S)-N-(2-hydroxynaphthalen-1-yl)(pyrrolidine-2-carboxamide)

• 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: (S)-N-(2-hydroxynaphthalen-1-yl)(pyrrolidine-2-carboxamide)
• 英文别名: (2S)-N-(2-hydroxynaphthalen-1-yl)pyrrolidine-2-carboxamide
• 化学式: C₁₅H₁₆N₂O₂
• 分子量: 256.304
• InChiKey: GXPQOISSOCIKHI-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  61.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-氨基-2-萘酚 在 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 (S)-N-(2-hydroxynaphthalen-1-yl)(pyrrolidine-2-carboxamide)
  参考文献：
  名称：

  Direct asymmetric aldol reaction catalyzed by simple prolinamide phenols

  摘要：

  Simple prolinamides 1a-f were synthesized, and their catalytic effects on the direct asymmetric aldol reactions in organic solvents and in water were evaluated. Prolinamide phenols 1a-d were found to be effective catalysts for the reaction of aromatic aldehydes with cyclohexanone in neat ketone and in water. The anti-aldol products were obtained with up to 98/2 anti/syn ratio and 96% ee in neat ketone, 98/2 anti/syn ratio and 99% ee in water, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.12.008
• 作为试剂：
  描述：

  邻硝基苯甲醛 、 环己酮 在 (S)-N-(2-hydroxynaphthalen-1-yl)(pyrrolidine-2-carboxamide) 作用下， 反应 48.0h， 生成 (2R)-2-((S)-hydroxy-(2-nitrophenyl)methyl)cyclohexan-1-one 、 (S)-2-[(R)-hydroxy(2-nitrophenyl)methyl]cyclohexan-1-one 、 2-[hydroxy(2-nitrophenyl)methyl]cyclohexanone
  参考文献：
  名称：

  Direct asymmetric aldol reaction catalyzed by simple prolinamide phenols

  摘要：

  Simple prolinamides 1a-f were synthesized, and their catalytic effects on the direct asymmetric aldol reactions in organic solvents and in water were evaluated. Prolinamide phenols 1a-d were found to be effective catalysts for the reaction of aromatic aldehydes with cyclohexanone in neat ketone and in water. The anti-aldol products were obtained with up to 98/2 anti/syn ratio and 96% ee in neat ketone, 98/2 anti/syn ratio and 99% ee in water, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.12.008

文献信息

• Direct asymmetric aldol reaction catalyzed by simple prolinamide phenols
  作者：Yu-Qin Fu、Zai-Chun Li、Li-Na Ding、Jing-Chao Tao、Sheng-Hong Zhang、Ming-Sheng Tang

  DOI：10.1016/j.tetasy.2006.12.008

  日期：2006.12

  Simple prolinamides 1a-f were synthesized, and their catalytic effects on the direct asymmetric aldol reactions in organic solvents and in water were evaluated. Prolinamide phenols 1a-d were found to be effective catalysts for the reaction of aromatic aldehydes with cyclohexanone in neat ketone and in water. The anti-aldol products were obtained with up to 98/2 anti/syn ratio and 96% ee in neat ketone, 98/2 anti/syn ratio and 99% ee in water, respectively. (c) 2006 Elsevier Ltd. All rights reserved.