2-bromohexadecanoic acid tert-butyl ester | 141186-22-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-bromohexadecanoic acid tert-butyl ester
• 英文别名: 2-Bromohexadecanoic acid t-butyl ester；tert-butyl 2-bromohexadecanoate
• CAS: 141186-22-3
• 化学式: C₂₀H₃₉BrO₂
• 分子量: 391.432
• InChiKey: PURDUEYPAIBZKH-UHFFFAOYSA-N

物化性质

• 沸点：
  362.9±10.0 °C(Predicted)
• 密度：
  1.041±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  23
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromohexadecanoic acid tert-butyl ester 在 potassium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Triaza-based amphiphilic chelators: Synthetic route, in vitro characterization and in vivo studies of their Ga(III) and Al(III) chelates

  摘要：

  Radiogallium chelates are important for diagnostic imaging in nuclear medicine (PET (positron emission tomography) and gamma-scintigraphy). Micelles are adequate colloidal vehicles for the delivery of therapeutic and diagnostic agents to organs and tissues. In this paper we describe the synthesis and in vitro and in vivo studies of a series of micelles-forming Ga(III) chelates targeted for the liver. The amphiphilic ligands are based on NOTA (NOTA = 1,4,7-triazacyclonoane-N,N'N ''-triacetic acid) and bear a alpha-alkyl chain in one of the pendant acetate arms (the size of the chain changes from four to fourteen carbon atoms). A multinuclear NMR study (H-1, C-13, Al-27 and Ga-71) gave some insights into the structure and dynamics of the metal chelates in solution, consistent with their rigidity and octahedral or pseudo-octahedral geometry. The critical micellar concentration of the chelates was determined using a fluorescence method and Al-27 NMR spectroscopy (Al (III) was used as a surrogate of Ga(III)), both showing similar results and suggesting that the chelates of NOTAC6 form pre-micellar aggregates. The logP (octanol-water) determination showed enhancement of the lipophilic character of the Ga(III) chelates with the increase of the number of carbons in the alpha-alkyl chain. Biodistribution and gamma-scintigraphic studies of the Ga-67(III) labeled chelates were performed on Wistar rats, showing higher liver uptake for [Ga-67](NOTAC8) in comparison to [Ga-67](NOTAC6), consistent with a longer alpha-alkyl chain and a higher lipophilicity. After 24 h both chelates were completely cleared off from the tissues and organs with no deposition in the bones and liver/spleen. [Ga-67](NOTAC8) showed high kinetic stability in blood serum. (c) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2010.06.002
• 作为产物：
  描述：

  2-溴十六烷酸 、 叔丁基三氯乙酰亚胺酯 在 三氟化硼乙醚 作用下， 以 二氯甲烷 、 N,N-二甲基乙酰胺 、 环己烷 为溶剂， 以73.5%的产率得到2-bromohexadecanoic acid tert-butyl ester
  参考文献：
  名称：

  Triaza-based amphiphilic chelators: Synthetic route, in vitro characterization and in vivo studies of their Ga(III) and Al(III) chelates

  摘要：

  Radiogallium chelates are important for diagnostic imaging in nuclear medicine (PET (positron emission tomography) and gamma-scintigraphy). Micelles are adequate colloidal vehicles for the delivery of therapeutic and diagnostic agents to organs and tissues. In this paper we describe the synthesis and in vitro and in vivo studies of a series of micelles-forming Ga(III) chelates targeted for the liver. The amphiphilic ligands are based on NOTA (NOTA = 1,4,7-triazacyclonoane-N,N'N ''-triacetic acid) and bear a alpha-alkyl chain in one of the pendant acetate arms (the size of the chain changes from four to fourteen carbon atoms). A multinuclear NMR study (H-1, C-13, Al-27 and Ga-71) gave some insights into the structure and dynamics of the metal chelates in solution, consistent with their rigidity and octahedral or pseudo-octahedral geometry. The critical micellar concentration of the chelates was determined using a fluorescence method and Al-27 NMR spectroscopy (Al (III) was used as a surrogate of Ga(III)), both showing similar results and suggesting that the chelates of NOTAC6 form pre-micellar aggregates. The logP (octanol-water) determination showed enhancement of the lipophilic character of the Ga(III) chelates with the increase of the number of carbons in the alpha-alkyl chain. Biodistribution and gamma-scintigraphic studies of the Ga-67(III) labeled chelates were performed on Wistar rats, showing higher liver uptake for [Ga-67](NOTAC8) in comparison to [Ga-67](NOTAC6), consistent with a longer alpha-alkyl chain and a higher lipophilicity. After 24 h both chelates were completely cleared off from the tissues and organs with no deposition in the bones and liver/spleen. [Ga-67](NOTAC8) showed high kinetic stability in blood serum. (c) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2010.06.002

文献信息

• [EN] NOVEL DRUG DELIVERY SYSTEMS FOR PROTEINS AND PEPTIDES USING ALBUMIN AS A CARRIER MOLECULE
  申请人：UNIVERSITY OF IOWA RESEARCH FOUNDATION

  公开号：WO1992001476A1

  公开（公告）日：1992-02-06

  (EN) A drug delivery system for proteins and peptides using albumin as a carrier molecule. The drug is bound noncovalently to albumin by means of an attached apolar substituent, preferably a long chain fatty acid derivative.(FR) L'invention se rapporte à un système de libération de médicaments pour protéines et peptides qui utilise de l'albumine comme molécule porteuse. Le médicament est lié par liaison non covalente à l'albumine au moyen d'un substituant apolaire attaché tel que de préférence un dérivé d'acides gras à chaÎne longue.