N-((1R,2R)-2-aminocyclohexyl)-1,1,1-trifluoromethanesulfonamide | 1023284-00-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-((1R,2R)-2-aminocyclohexyl)-1,1,1-trifluoromethanesulfonamide
• 英文别名: N-[(1R,2R)-2-aminocyclohexyl]-1,1,1-trifluoromethanesulfonamide
• CAS: 1023284-00-5
• 化学式: C₇H₁₃F₃N₂O₂S
• 分子量: 246.254
• InChiKey: GZWHPKPKHTUWSS-PHDIDXHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  80.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  三氟甲磺酸酐 、 2-((1R,2R)-2-aminocyclohexyl)isoindoline-1,3-dione 在 盐酸 、 一水合肼 作用下， 以 二氯甲烷 、 水 、 乙醇 为溶剂， 反应 2.0h， 以31%的产率得到N-((1R,2R)-2-aminocyclohexyl)-1,1,1-trifluoromethanesulfonamide
  参考文献：
  名称：

  The effect of hydrogen bond donors in asymmetric organocatalytic conjugate additions

  摘要：

  A series of primary amine organocatalysts with various hydrogen bond donors were prepared and examined in the conjugate addition of isobutyraldehyde and acetone to trans-beta-nitrostyrene and (E)-methyl 2-oxo-4-phenylbut-3-enoate. The effect of N-H acidity and hydrogen-bonding modes of the catalysts on the catalytic activity and enantioselectivity was studied. The experimental results did not support a general correlation of N-H acidity and hydrogen-bonding modes with catalytic activity and enantioselectivity. The catalysts with double hydrogen-bonding interactions provided better catalytic activities and enantioselectivities than the catalysts with single hydrogen-bonding interactions for the reaction of trans-beta-nitrostyrene. The catalyst with the most acidic N-H bond showed the best catalytic activity and enantioselectivity for the reaction of (E)-methyl 2-oxo-4-phenylbut-3-enoate. These results suggest that the effect of hydrogen bond donors in organocatalytic reactions may be highly dependent on the substrates and the reaction conditions. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.11.029
• 作为试剂：
  描述：

  异丁醛 、 2-氧代-4-苯基-3-丁酸甲酯 在 N-((1R,2R)-2-aminocyclohexyl)-1,1,1-trifluoromethanesulfonamide 、 苯甲酸 、 pyridinium chlorochromate 作用下， 以 氯仿 、 二氯甲烷 为溶剂， 反应 54.0h， 生成 methyl 3,3-dimethyl-2-oxo-4-phenyl-3,4-dihydro-2H-pyran-6-carboxylate 、 methyl 3,3-dimethyl-2-oxo-4-phenyl-3,4-dihydro-2H-pyran-6-carboxylate
  参考文献：
  名称：

  The effect of hydrogen bond donors in asymmetric organocatalytic conjugate additions

  摘要：

  A series of primary amine organocatalysts with various hydrogen bond donors were prepared and examined in the conjugate addition of isobutyraldehyde and acetone to trans-beta-nitrostyrene and (E)-methyl 2-oxo-4-phenylbut-3-enoate. The effect of N-H acidity and hydrogen-bonding modes of the catalysts on the catalytic activity and enantioselectivity was studied. The experimental results did not support a general correlation of N-H acidity and hydrogen-bonding modes with catalytic activity and enantioselectivity. The catalysts with double hydrogen-bonding interactions provided better catalytic activities and enantioselectivities than the catalysts with single hydrogen-bonding interactions for the reaction of trans-beta-nitrostyrene. The catalyst with the most acidic N-H bond showed the best catalytic activity and enantioselectivity for the reaction of (E)-methyl 2-oxo-4-phenylbut-3-enoate. These results suggest that the effect of hydrogen bond donors in organocatalytic reactions may be highly dependent on the substrates and the reaction conditions. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.11.029

文献信息

• Process for producing optically active compound
  申请人：Kanto Kagaku Kabushiki Kaisha

  公开号：EP1439159B1

  公开（公告）日：2007-06-20
• Process for preparing optically active alcohols
  申请人：Japan Science and Technology Agency

  公开号：EP1300381B1

  公开（公告）日：2006-03-08
• The effect of hydrogen bond donors in asymmetric organocatalytic conjugate additions
  作者：Jin-hua Lao、Xue-jing Zhang、Jin-jia Wang、Xue-ming Li、Ming Yan、Hai-bin Luo

  DOI：10.1016/j.tetasy.2009.11.029

  日期：2009.12

  A series of primary amine organocatalysts with various hydrogen bond donors were prepared and examined in the conjugate addition of isobutyraldehyde and acetone to trans-beta-nitrostyrene and (E)-methyl 2-oxo-4-phenylbut-3-enoate. The effect of N-H acidity and hydrogen-bonding modes of the catalysts on the catalytic activity and enantioselectivity was studied. The experimental results did not support a general correlation of N-H acidity and hydrogen-bonding modes with catalytic activity and enantioselectivity. The catalysts with double hydrogen-bonding interactions provided better catalytic activities and enantioselectivities than the catalysts with single hydrogen-bonding interactions for the reaction of trans-beta-nitrostyrene. The catalyst with the most acidic N-H bond showed the best catalytic activity and enantioselectivity for the reaction of (E)-methyl 2-oxo-4-phenylbut-3-enoate. These results suggest that the effect of hydrogen bond donors in organocatalytic reactions may be highly dependent on the substrates and the reaction conditions. (C) 2009 Elsevier Ltd. All rights reserved.