(1S,3R,5R)-3-Hydroxy-3-quinolin-8-yl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester | 863394-52-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (1S,3R,5R)-3-Hydroxy-3-quinolin-8-yl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester
• CAS: 863394-52-9
• 化学式: C₂₁H₂₆N₂O₃
• 分子量: 354.449
• InChiKey: FGNFCXVKZBFNQJ-JIPZTSHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  26.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  62.66
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1S,3R,5R)-3-Hydroxy-3-quinolin-8-yl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 8-[8-((S)-8-Methoxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-8-aza-bicyclo[3.2.1]oct-2-en-3-yl]-quinoline
  参考文献：
  名称：

  Modulation of selective serotonin reuptake inhibitor and 5-HT1A antagonist activity in 8-aza-bicyclo[3.2.1]octane derivatives of 2,3-dihydro-1,4-benzodioxane

  摘要：

  2,3-Dihydro-1,4-benzodioxanes with aryl 8-aza-bicyclo[3.2.1]oct-3-ene attachments 2 produce compounds with potent 5-HT-T affinity, and weak 5-HT1A affinity and a, affinity. This compares with 2,3-dihydro-1,4-benzodioxanes containing 8-aza-bicyclo[3.2.1] octan-3-ol attachments 4 which possess potent 5-HT1A affinity, moderate to good selectivity over a, and little 5-HT-T affinity. A 3-benzothiophene analogue of 4 (30) was synthesized which possesses potent 5-HT1A affinity and especially good selectivity over both a, and 5-HT-T. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.10.024
• 作为产物：
  描述：

  去甲托品酮 在 sodium hydroxide 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 生成 (1S,3R,5R)-3-Hydroxy-3-quinolin-8-yl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Modulation of selective serotonin reuptake inhibitor and 5-HT1A antagonist activity in 8-aza-bicyclo[3.2.1]octane derivatives of 2,3-dihydro-1,4-benzodioxane

  摘要：

  2,3-Dihydro-1,4-benzodioxanes with aryl 8-aza-bicyclo[3.2.1]oct-3-ene attachments 2 produce compounds with potent 5-HT-T affinity, and weak 5-HT1A affinity and a, affinity. This compares with 2,3-dihydro-1,4-benzodioxanes containing 8-aza-bicyclo[3.2.1] octan-3-ol attachments 4 which possess potent 5-HT1A affinity, moderate to good selectivity over a, and little 5-HT-T affinity. A 3-benzothiophene analogue of 4 (30) was synthesized which possesses potent 5-HT1A affinity and especially good selectivity over both a, and 5-HT-T. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.10.024