(1R,2R)-2-Dibutylamino-indan-1-ol | 192197-88-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (1R,2R)-2-Dibutylamino-indan-1-ol
• 英文别名: (1R,2R)-2-(dibutylamino)-2,3-dihydro-1H-inden-1-ol
• CAS: 192197-88-9
• 化学式: C₁₇H₂₇NO
• 分子量: 261.407
• InChiKey: BJJGQQFXGBHQEO-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2R)-2-Dibutylamino-indan-1-ol 在 二异丁基氢化铝 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 94.0h， 生成 (1S,2R)-2-Dibutylamino-indan-1-ol
  参考文献：
  名称：

  New indane derived aminoalcohols as chiral ligands for the catalytic enantioselective addition of diethylzinc to aldehydes

  摘要：

  Secondary amines react with (1R,2S)-indene oxide 1 in a completely regioselective manner leading to trans-2-dialkylamino-1-indanols 4a-d in high yield. A Mitsunobu inversion via the corresponding p-nitrobenzoates, followed by reduction with DIBALH leads to the cis-2-dialkylamino-1-indanols 5a-d also in high yield. These two new classes of aminoindanols have been tested as chiral ligands for the enantioselective addition of diethylzinc to both aliphatic and aromatic aldehydes, leading to 1-substituted 1-propanols with up to 80% e.e. A very simple procedure for the enantiomeric enrichment of 1 from 88% to greater than or equal to 99% e.e. is also reported. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00163-8
• 作为产物：
  描述：

  (1aR,6aS)-6,6a-dihydro-1aH-indeno[1,2-b]oxirene 、 二正丁胺 在 lithium perchlorate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 (1R,2R)-2-Dibutylamino-indan-1-ol
  参考文献：
  名称：

  New indane derived aminoalcohols as chiral ligands for the catalytic enantioselective addition of diethylzinc to aldehydes

  摘要：

  Secondary amines react with (1R,2S)-indene oxide 1 in a completely regioselective manner leading to trans-2-dialkylamino-1-indanols 4a-d in high yield. A Mitsunobu inversion via the corresponding p-nitrobenzoates, followed by reduction with DIBALH leads to the cis-2-dialkylamino-1-indanols 5a-d also in high yield. These two new classes of aminoindanols have been tested as chiral ligands for the enantioselective addition of diethylzinc to both aliphatic and aromatic aldehydes, leading to 1-substituted 1-propanols with up to 80% e.e. A very simple procedure for the enantiomeric enrichment of 1 from 88% to greater than or equal to 99% e.e. is also reported. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00163-8