(1R,3R,5S)-3-(3,4-Dichloro-phenyl)-3-hydroxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester | 863394-54-1

• 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,3R,5S)-3-(3,4-Dichloro-phenyl)-3-hydroxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester
• CAS: 863394-54-1
• 化学式: C₁₈H₂₃Cl₂NO₃
• 分子量: 372.292
• InChiKey: WQPZDXCZRCCBEY-MCBXIFIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.74
• 重原子数：
  24.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  49.77
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1R,3R,5S)-3-(3,4-Dichloro-phenyl)-3-hydroxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester 在 potassium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 (S)-1-[3-(3,4-Dichloro-phenyl)-8-aza-bicyclo[3.2.1]oct-2-en-8-yl]-3-(1H-indol-4-yloxy)-propan-2-ol
  参考文献：
  名称：

  Novel aryloxy-8-azabicyclo[3.2.1]oct-3-enes with 5-HT transporter and 5-HT1A affinity

  摘要：

  Joining aryl 8-azabicyclo[3.2.1]oct-3-enes with aryloxyethanes and aryloxypropanes produces novel series of compounds 11 and 12 with potent 5-HT-T affinity and moderately potent 5-HT1A affinity. Moreover, several of these compounds possess functional 5-HT1A antagonism. Optimal compounds are, 4-indolyloxyethane 21, 4-indolyloxypropanes 25, and 27, which possess potent 5-HT-T affinity (5-HT-T K-i: 21: 1.2 nM, 25: 0.54 nM, 27: 0.38 nM) and good 5-HT1A affinity/antagonism (5-HT1A K-i, [S-35]GTPgammaS: E-max (%): 21: 111.1 nM, 0% 25: 173.2 nM, 0%; 27: 107 nM, 0%). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.08.030
• 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 (1R,3R,5S)-3-(3,4-Dichloro-phenyl)-3-hydroxy-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