(1R,4S,5S)-8-tert-butoxycarbonyl-4-(1'-hydroxyethyl)-8-azabicyclo[3.2.1]octan-3-one | 496047-64-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 英文名称: (1R,4S,5S)-8-tert-butoxycarbonyl-4-(1'-hydroxyethyl)-8-azabicyclo[3.2.1]octan-3-one
• 英文别名: Tert-butyl (1S,2S,5R)-2-(1-hydroxyethyl)-3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate
• CAS: 496047-64-4
• 化学式: C₁₄H₂₃NO₄
• 分子量: 269.341
• InChiKey: NYSTWAOXFDACQT-KMIYQGBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,4S,5S)-8-tert-butoxycarbonyl-4-(1'-hydroxyethyl)-8-azabicyclo[3.2.1]octan-3-one 在 三乙胺 咪唑 、 甲酸 、 potassium tert-butylate 、 四丁基氟化铵 、 palladium diacetate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 、 pyridinium chlorochromate 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.75h， 生成 (1S,5R)-2-acetyl-8-azabicyclo<3.2.1>octa-2-ene
  参考文献：
  名称：

  A new divergent synthesis of (+)- and (−)-ferruginine utilizing PLE-catalyzed asymmetric dealkoxycarbonylation

  摘要：

  A new divergent synthesis of (+)- and (-)-ferruginine 4, via the optically active 8-benzyl-3-oxo-8-azabicy-clo[3.2.1]octane-2-carboxylates 6 is described. The P-keto ester intermediates 6 were prepared by a novel PLE-catalyzed asymmetric dealkoxycarbonylation of the symmetric tropinone-type diesters 5. The key problem in the synthesis is controlling the regioselectivity of the reaction at the 2- and 4-positions in the tropane framework of the P-keto ester 6 for introduction of the acetyl group. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00657-2
• 作为产物：
  描述：

  benzyl (1R,5S)-8-tert-butoxycarbonyl-4-(1'-hydroxyethyl)-3-oxo-8-azabicyclo[3.2.1]octan-2-carboxylate 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 反应 26.0h， 生成 (1R,4S,5S)-8-tert-butoxycarbonyl-4-(1'-hydroxyethyl)-8-azabicyclo[3.2.1]octan-3-one
  参考文献：
  名称：

  A new divergent synthesis of (+)- and (−)-ferruginine utilizing PLE-catalyzed asymmetric dealkoxycarbonylation

  摘要：

  A new divergent synthesis of (+)- and (-)-ferruginine 4, via the optically active 8-benzyl-3-oxo-8-azabicy-clo[3.2.1]octane-2-carboxylates 6 is described. The P-keto ester intermediates 6 were prepared by a novel PLE-catalyzed asymmetric dealkoxycarbonylation of the symmetric tropinone-type diesters 5. The key problem in the synthesis is controlling the regioselectivity of the reaction at the 2- and 4-positions in the tropane framework of the P-keto ester 6 for introduction of the acetyl group. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00657-2

文献信息

• A new divergent synthesis of (+)- and (−)-ferruginine utilizing PLE-catalyzed asymmetric dealkoxycarbonylation
  作者：Takahiro Katoh、Kiyoshi Kakiya、Takashi Nakai、Soichi Nakamura、Kiyoharu Nishide、Manabu Node

  DOI：10.1016/s0957-4166(02)00657-2

  日期：2002.10

  A new divergent synthesis of (+)- and (-)-ferruginine 4, via the optically active 8-benzyl-3-oxo-8-azabicy-clo[3.2.1]octane-2-carboxylates 6 is described. The P-keto ester intermediates 6 were prepared by a novel PLE-catalyzed asymmetric dealkoxycarbonylation of the symmetric tropinone-type diesters 5. The key problem in the synthesis is controlling the regioselectivity of the reaction at the 2- and 4-positions in the tropane framework of the P-keto ester 6 for introduction of the acetyl group. (C) 2002 Elsevier Science Ltd. All rights reserved.