1-[(4aR,10bR)-2,3,4a,5,6,10b-六氢-9-(三异丙基硅氧基)-4H-萘并[1,2-b]-1,4-恶嗪-4-基]乙酮 | 1034706-81-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: 1-[(4aR,10bR)-2,3,4a,5,6,10b-六氢-9-(三异丙基硅氧基)-4H-萘并[1,2-b]-1,4-恶嗪-4-基]乙酮
• 英文名称: (+)-N-acetyl-3,4,4a,5,6,10b-hexahydro-2H-naphtho[1,2-b][1,4]oxazine-9-ol triisopropylsilyl ether
• 英文别名: (+)-N-Acetyl 3,4,4a,5,6,10b-Hexahydro-2H-naphtho[1,2-b][1,4]oxazine-9-ol Triisopropylsilyl Ether；1-[(4aR,10bR)-9-tri(propan-2-yl)silyloxy-2,3,4a,5,6,10b-hexahydrobenzo[h][1,4]benzoxazin-4-yl]ethanone
• CAS: 1034706-81-4
• 化学式: C₂₃H₃₇NO₃Si
• 分子量: 403.637
• InChiKey: XZZQCTZCKHVBLF-DHIUTWEWSA-N

物化性质

• 密度：
  1.023
• 溶解度：
  可溶于氯仿、乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  5.48
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[(4aR,10bR)-2,3,4a,5,6,10b-六氢-9-(三异丙基硅氧基)-4H-萘并[1,2-b]-1,4-恶嗪-4-基]乙酮 在 lithium aluminium tetrahydride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 生成 (+)-(3-¹³C)propyl-3,4,4a,5,6,10b-hexahydro-2H-naphtho[1,2-b][1,4]oxazin-9-ol
  参考文献：
  名称：

  Synthesis of the dopamine D2/D3 receptor agonist (+)-PHNO via supercritical fluid chromatography: preliminary PET imaging study with [3-11C]-(+)PHNO

  摘要：

  Carbon-11 labeled (+)-4-[1-C-11]propyl-3,4,4a,5,6,10b-hexahydro-2H-naphtho[1,2-b][1,4]oxazin-9-ol ([1-(11)]-(+)-PHNO) is a dopamine D-3-preferring agonist radiopharmaceutical used for medical imaging by positron emission tomography (PET). We report the synthesis of (+)-PHNO using supercritical fluid chromatography for enantiomeric resolution of its norpropyl derivative, HNO, followed by propylation. (+)-HNO was used to prepare the radiolabeling precursor, (+)-trans-4-acetyl-9-triisopropylsilyloxy-2,3,4a,5,6,10b-hexahydro-4H-naphth[1,2b)][1,4]oxazine, in 12 steps. Modifications to the labeling procedure were made to ensure consistent preparation of [3-C-11]-(+)-PHNO via [C-11[CH3I. A preliminary PET imaging study was carried out with this tracer in an attempt to image dopamine receptors in brown adipose tissue (brown fat) in vivo. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2013.11.113
• 作为产物：
  描述：

  7-甲氧基-1-萘满酮 在 吡啶 、 咪唑 、 aluminum (III) chloride 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 5%-palladium/activated carbon 、 盐酸羟胺 、 potassium ethoxide 、 氢气 、 sodium hydride 、 potassium carbonate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 、 mineral oil 、 苯 为溶剂， 反应 95.0h， 生成 1-[(4aR,10bR)-2,3,4a,5,6,10b-六氢-9-(三异丙基硅氧基)-4H-萘并[1,2-b]-1,4-恶嗪-4-基]乙酮
  参考文献：
  名称：

  Synthesis of the dopamine D2/D3 receptor agonist (+)-PHNO via supercritical fluid chromatography: preliminary PET imaging study with [3-11C]-(+)PHNO

  摘要：

  Carbon-11 labeled (+)-4-[1-C-11]propyl-3,4,4a,5,6,10b-hexahydro-2H-naphtho[1,2-b][1,4]oxazin-9-ol ([1-(11)]-(+)-PHNO) is a dopamine D-3-preferring agonist radiopharmaceutical used for medical imaging by positron emission tomography (PET). We report the synthesis of (+)-PHNO using supercritical fluid chromatography for enantiomeric resolution of its norpropyl derivative, HNO, followed by propylation. (+)-HNO was used to prepare the radiolabeling precursor, (+)-trans-4-acetyl-9-triisopropylsilyloxy-2,3,4a,5,6,10b-hexahydro-4H-naphth[1,2b)][1,4]oxazine, in 12 steps. Modifications to the labeling procedure were made to ensure consistent preparation of [3-C-11]-(+)-PHNO via [C-11[CH3I. A preliminary PET imaging study was carried out with this tracer in an attempt to image dopamine receptors in brown adipose tissue (brown fat) in vivo. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2013.11.113

文献信息

• WO2008/75043
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis of the dopamine D2/D3 receptor agonist (+)-PHNO via supercritical fluid chromatography: preliminary PET imaging study with [3-11C]-(+)PHNO
  作者：Timothy M. Shoup、John P. McCauley、David F. Lee、Rui Chen、Marc D. Normandin、Ali A. Bonab、Georges El Fakhri、Neil Vasdev

  DOI：10.1016/j.tetlet.2013.11.113

  日期：2014.1

  Carbon-11 labeled (+)-4-[1-C-11]propyl-3,4,4a,5,6,10b-hexahydro-2H-naphtho[1,2-b][1,4]oxazin-9-ol ([1-(11)]-(+)-PHNO) is a dopamine D-3-preferring agonist radiopharmaceutical used for medical imaging by positron emission tomography (PET). We report the synthesis of (+)-PHNO using supercritical fluid chromatography for enantiomeric resolution of its norpropyl derivative, HNO, followed by propylation. (+)-HNO was used to prepare the radiolabeling precursor, (+)-trans-4-acetyl-9-triisopropylsilyloxy-2,3,4a,5,6,10b-hexahydro-4H-naphth[1,2b)][1,4]oxazine, in 12 steps. Modifications to the labeling procedure were made to ensure consistent preparation of [3-C-11]-(+)-PHNO via [C-11[CH3I. A preliminary PET imaging study was carried out with this tracer in an attempt to image dopamine receptors in brown adipose tissue (brown fat) in vivo. Published by Elsevier Ltd.