2,2,2-trichloro-N-((1R,2R,3S,5R)-2-hydroxy-2-hydroxymethyl-6,6-dimethylbicyclo[3.1.1]heptan-3-yl)acetamide | 1370261-51-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2,2,2-trichloro-N-((1R,2R,3S,5R)-2-hydroxy-2-hydroxymethyl-6,6-dimethylbicyclo[3.1.1]heptan-3-yl)acetamide
• CAS: 1370261-51-0
• 化学式: C₁₂H₁₈Cl₃NO₃
• 分子量: 330.639
• InChiKey: UIBCYWVAMOCVNZ-HGIWHZBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  69.56
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2,2,2-trichloro-N-((1R,2R,3S,5R)-2-hydroxy-2-hydroxymethyl-6,6-dimethylbicyclo[3.1.1]heptan-3-yl)acetamide 在 盐酸 、 potassium hydroxide 作用下， 以 乙醚 、 乙醇 、 水 为溶剂， 反应 50.0h， 生成 (1R,2R,3S,5R)-3-cyclohexylamino-2-hydroxymethyl-6,6-dimethylbicyclo[3.1.1]heptan-2-ol
  参考文献：
  名称：

  Stereoselective synthesis of pinane-type tridentate aminodiols and their application in the enantioselective addition of diethylzinc to benzaldehyde

  摘要：

  A library of pinane-based aminodiols were prepared from commercially available (1R)-(-)-myrtenol (-)-1. Compound (-)-1 was transformed into ally! trichloroacetamide (+)-2 via the acetimidate, followed by the Overman rearrangement. In order obtain the aminodiol structure, (+)-2 was subjected to stereoselective dihydroxylation with OsO4, resulting in dihydroxy trichloroacetamide (+)-3. The trichloroacetyl group was removed from (+)-3 with aqueous HCl and the (1R,2R,3S,5R)-3-amino-2-hydroxymethyl-6,6-dimethylbicyclo[3.1.1]heptan-2-ol hydrochloride (-)-4 obtained was transformed to primary, secondary and tertiary aminodiols by reductive amination, N-alkylation of aminodiol (+)-9 and debenzylation of N-benzyl aminodiol (+)-10, respectively. In the reactions of (+)-9 and (+)-14 with formaldehyde, highly regioselective ring closure was observed. In contrast with earlier results, the aminodiols gave pinane-fused oxazolidines (+)-11 and (-)-15. The aminodiols and their oxazolidine derivatives 5-15 were applied as chiral catalysts in the enantioselective addition of diethylzinc to benzaldehyde. The best enantioselectivity was observed in the case of the N-benzyl-substituted derivative (+)-9. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.01.020
• 作为产物：
  描述：

  (-)-桃金娘烯醇 在 四氧化锇 、 N-甲基吗啉氧化物 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 48.0h， 生成 2,2,2-trichloro-N-((1R,2R,3S,5R)-2-hydroxy-2-hydroxymethyl-6,6-dimethylbicyclo[3.1.1]heptan-3-yl)acetamide
  参考文献：
  名称：

  Stereoselective synthesis of pinane-type tridentate aminodiols and their application in the enantioselective addition of diethylzinc to benzaldehyde

  摘要：

  A library of pinane-based aminodiols were prepared from commercially available (1R)-(-)-myrtenol (-)-1. Compound (-)-1 was transformed into ally! trichloroacetamide (+)-2 via the acetimidate, followed by the Overman rearrangement. In order obtain the aminodiol structure, (+)-2 was subjected to stereoselective dihydroxylation with OsO4, resulting in dihydroxy trichloroacetamide (+)-3. The trichloroacetyl group was removed from (+)-3 with aqueous HCl and the (1R,2R,3S,5R)-3-amino-2-hydroxymethyl-6,6-dimethylbicyclo[3.1.1]heptan-2-ol hydrochloride (-)-4 obtained was transformed to primary, secondary and tertiary aminodiols by reductive amination, N-alkylation of aminodiol (+)-9 and debenzylation of N-benzyl aminodiol (+)-10, respectively. In the reactions of (+)-9 and (+)-14 with formaldehyde, highly regioselective ring closure was observed. In contrast with earlier results, the aminodiols gave pinane-fused oxazolidines (+)-11 and (-)-15. The aminodiols and their oxazolidine derivatives 5-15 were applied as chiral catalysts in the enantioselective addition of diethylzinc to benzaldehyde. The best enantioselectivity was observed in the case of the N-benzyl-substituted derivative (+)-9. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.01.020