(1S,3R,4R,6R)-3-(benzyl(methyl)amino)methyl-7,7-dimethylbicyclo[4.1.0]heptane-3,4-diol | 1330616-17-5

• 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: (1S,3R,4R,6R)-3-(benzyl(methyl)amino)methyl-7,7-dimethylbicyclo[4.1.0]heptane-3,4-diol
• 英文别名: (1S,3R,4R,6R)-3-[[benzyl(methyl)amino]methyl]-7,7-dimethylbicyclo[4.1.0]heptane-3,4-diol
• CAS: 1330616-17-5
• 化学式: C₁₈H₂₇NO₂
• 分子量: 289.418
• InChiKey: VJRDAPVQAJNVRG-KYHPRHEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  43.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,3R,4R,6R)-3-(benzyl(methyl)amino)methyl-7,7-dimethylbicyclo[4.1.0]heptane-3,4-diol 在 5% Pd(II)/C(eggshell) 、 氢气 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 反应 6.0h， 生成 (1aR,2aR,6aR,7aS)-6a-hydroxy-1,1,5-trimethyldecahydro-3-oxa-5-azacyclopropa[g]naphthalene
  参考文献：
  名称：

  Stereoselective synthesis of carane-based aminodiols as chiral ligands for the catalytic addition of diethylzinc to aldehydes

  摘要：

  Key intermediate epoxy alcohol 4 was prepared regio- and stereoselectively from (+)-3-carene 1 via carene oxide 2 and (-)-trans-allyl alcohol 3. The lithium perchlorate-catalysed ring opening of 4 with secondary and primary achiral and chiral amines resulted in primary, secondary and tertiary aminodiols. Aminodiols 5-14 were applied as chiral catalysts in the enantioselective addition of diethylzinc to benzaldehyde, resulting in (R)- and (S)-1-phenyl-1-propanol with moderate enantioselectivity. N-Benzyl. N-methyl, and (S)- and (R)-N-methylbenzyl derivatives 7 and 10-13 were transformed into 1,3-oxazines 17-21 via highly regioselective ring closures. When 17-21 were applied as chiral catalysts in the addition of diethylzinc to aromatic and aliphatic aldehydes, high chiral induction in the tricyclic catalysts was observed. The effects of the substituents on the nitrogen of the aminodiols and 1,3-oxazines were studied in detail: the best enantioselectivity was observed in the case of N-methylbenzyl-substituted oxazine 19. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.06.013
• 作为产物：
  描述：

  (+)-3-蒈烯 在 2,2,6,6-四甲基哌啶 、 正丁基锂 、 sodium phosphate dibasic dodecahydrate 、 lithium perchlorate 、 氯化二乙基铝 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 氯仿 、 甲苯 、 乙腈 为溶剂， 反应 12.0h， 生成 (1S,3R,4R,6R)-3-(benzyl(methyl)amino)methyl-7,7-dimethylbicyclo[4.1.0]heptane-3,4-diol
  参考文献：
  名称：

  Stereoselective synthesis of carane-based aminodiols as chiral ligands for the catalytic addition of diethylzinc to aldehydes

  摘要：

  Key intermediate epoxy alcohol 4 was prepared regio- and stereoselectively from (+)-3-carene 1 via carene oxide 2 and (-)-trans-allyl alcohol 3. The lithium perchlorate-catalysed ring opening of 4 with secondary and primary achiral and chiral amines resulted in primary, secondary and tertiary aminodiols. Aminodiols 5-14 were applied as chiral catalysts in the enantioselective addition of diethylzinc to benzaldehyde, resulting in (R)- and (S)-1-phenyl-1-propanol with moderate enantioselectivity. N-Benzyl. N-methyl, and (S)- and (R)-N-methylbenzyl derivatives 7 and 10-13 were transformed into 1,3-oxazines 17-21 via highly regioselective ring closures. When 17-21 were applied as chiral catalysts in the addition of diethylzinc to aromatic and aliphatic aldehydes, high chiral induction in the tricyclic catalysts was observed. The effects of the substituents on the nitrogen of the aminodiols and 1,3-oxazines were studied in detail: the best enantioselectivity was observed in the case of N-methylbenzyl-substituted oxazine 19. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.06.013

文献信息

• Stereoselective synthesis of carane-based aminodiols as chiral ligands for the catalytic addition of diethylzinc to aldehydes
  作者：Zsolt Szakonyi、Kinga Csillag、Ferenc Fülöp

  DOI：10.1016/j.tetasy.2011.06.013

  日期：2011.5

  Key intermediate epoxy alcohol 4 was prepared regio- and stereoselectively from (+)-3-carene 1 via carene oxide 2 and (-)-trans-allyl alcohol 3. The lithium perchlorate-catalysed ring opening of 4 with secondary and primary achiral and chiral amines resulted in primary, secondary and tertiary aminodiols. Aminodiols 5-14 were applied as chiral catalysts in the enantioselective addition of diethylzinc to benzaldehyde, resulting in (R)- and (S)-1-phenyl-1-propanol with moderate enantioselectivity. N-Benzyl. N-methyl, and (S)- and (R)-N-methylbenzyl derivatives 7 and 10-13 were transformed into 1,3-oxazines 17-21 via highly regioselective ring closures. When 17-21 were applied as chiral catalysts in the addition of diethylzinc to aromatic and aliphatic aldehydes, high chiral induction in the tricyclic catalysts was observed. The effects of the substituents on the nitrogen of the aminodiols and 1,3-oxazines were studied in detail: the best enantioselectivity was observed in the case of N-methylbenzyl-substituted oxazine 19. (C) 2011 Elsevier Ltd. All rights reserved.