1-(benzyloxy)octan-3-ol | 170798-94-4

• 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: 1-(benzyloxy)octan-3-ol
• 英文别名: 1-benzyloxy-3-octanol；1-Phenylmethoxyoctan-3-ol
• CAS: 170798-94-4
• 化学式: C₁₅H₂₄O₂
• 分子量: 236.354
• InChiKey: PODPQGGPKNEATR-UHFFFAOYSA-N

物化性质

• 沸点：
  359.3±17.0 °C(Predicted)
• 密度：
  0.976±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(benzyloxy)octan-3-ol 在 pyridinium chlorochromate 、 [双(2-甲氧基乙基)胺]三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 17.25h， 生成 ((3,3-difluorooctyloxy)methyl)benzene
  参考文献：
  名称：

  Regio-selective hydroxylation of gem-difluorinated octanes by alkane hydroxylase (AlkB)

  摘要：

  gem-Difluoromethylene substituted molecules constitute a distinct class of fluorinated compounds. In this study, special chemistry has been developed for their preparation based on the highly selective terminal hydroxylation of these gem-difluorinated octanes by AlkB (alkane hydroxylase) from Pseudomonas putida Gpo1 to form gem-difluorinated octan-1-ols. The hydroxylation reaction is performed by whole-cell catalysis. Identification of the distal- and proximal-hydroxylation products was made by H-1, C-13, and F-19 NMR; GC and GC/MSD; and/or by comparison with authentic standards in GC. To the best of our knowledge, we have obtained the first synthesis of 2,2-, 3,3- and 4,4-difluorooctan-1-ols, from simple and inexpensive starting materials. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.03.101
• 作为产物：
  描述：

  [(3-丁烯-1-基氧基)甲基]苯 在 正丁基锂 、 三甲基铝 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 1-(benzyloxy)octan-3-ol
  参考文献：
  名称：

  Pentacoordinate Organoaluminum Chemistry:  Catalytic Efficiency of Me₃Al in the Epoxide Cleavage with Alkynyllithiums

  摘要：

  A new and highly effective catalytic method for epoxide alkynylations has been developed that involves the chelation-controlled alkylation of heterosubstituted epoxides with Me3Al via pentacoordinate organoalluminum complexes by taking advantage of the exceedingly high affinity of aluminum to oxygen. For example, reaction of epoxy ether, (l-benzyloxy)-3-butene oxide (1), in toluene with PhC=CLi under the influence of catalytic Me3Al (10 mol%) proceeded smoothly at O degrees C for 5 h to furnish the alkynylation product, l-(benzyloxy)-6-phenylhex-5-yn-3-ol, in 76% yield [cf. 3% without Me3Al catalyst; 78% with stoichiometric Me3Al under similar conditions]. This represents the first catalytic procedure for the amphiphilic alkylation of epoxides. The participation of pentacoordinate Me3Al complexes of epoxy ethers of type 1 is emphasized by comparing the reactivity with the corresponding simple epoxide, 5-phenyl-l-pentene oxide, which was not susceptible to nucleophile attack of PhC=CLi with catalytic Me3A1 under similar conditions. The pentacoordinate complex formation of Me3Al with epoxy ether 1 is characterized by low-temperature C-13 and Al-27 NMR spectroscopy. This approach is also applicable to the selective alkynylation of tosyl aziridines with adjacent ether functionality, which provides a promising method for amino alcohol synthesis.

  DOI：

  10.1021/ja9842464

文献信息

• 18F-Labeled Octanoates as Potential Agents for Cerebral Fatty Acid Studies. The Influence of 4-Substitution and the Fluorine Position on Biodistribution.
  作者：Fumi NAGATSUGI、Fumiko INOUE、Shigeki SASAKI、Minoru MAEDA

  DOI：10.1248/cpb.43.607

  日期：——

  octanoic acid analogs. Radiochemical synthesis was achieved by the nucleophilic displacement of a tosylate or mesylate precursor with [18F]fluoride ion. Tissue distribution studies in rats showed low cerebral uptakes of these 18F-labeled fatty acid analogs with poor brain-to-blood ratios. 3-[18F]Fluorooctanoic acid showed considerable defluorination, evident as a high bone activity level. The initial uptake

  为了理解可能导致体内放射性示踪剂用于研究脑脂肪酸代谢的结构特征，已制备了在C4位具有甲基或宝石二甲基分支的8- [18F]氟辛酸酯衍生物。还已经合成了3- [18F]氟-和4- [18F]氟辛酸，用于研究氟位置对18F标记的辛酸类似物的体内行为的影响。放射性化学合成是通过[18F]氟离子对甲苯磺酸酯或甲磺酸酯前体进行亲核取代而实现的。在大鼠中进行的组织分布研究表明，这些18F标记的脂肪酸类似物的脑部摄取率低，脑血比低。3- [18F]氟辛酸显示出相当大的脱氟，明显表现为高骨活性。注射8- [18F]氟-4-甲基辛酸乙酯和4- [18F]-氟辛酸乙酯后，大脑中最初的活动初始吸收在较长的时间内几乎没有变化，这与之前对非支链类似物观察到的相似， 8- [18F]氟辛酸乙酯及其游离酸。相反，4-gem-二甲基分支的类似物被肝脏迅速并优先吸收。代谢物分析表明，在血液中发现了由8- [18F]氟-4-
• Prodrugs for liver specific drug delivery
  申请人：Erion D. Mark

  公开号：US20050101775A1

  公开（公告）日：2005-05-12

  The present invention is directed towards novel cyclic phosph(oramid)ate prodrugs of alcohol-, amine-, and thiol-containing drugs, their preparation, their synthetic intermediates, and their uses. Another aspect of the invention is the use of the prodrugs to treat diseases that benefit from enhanced drug distribution to the liver and like tissues and cells that express cytochrome P450, including hepatitis, cancer, liver fibrosis, malaria, other viral and parasitic infections, and metabolic diseases where the liver is responsible for the overproduction of the biochemical end product, e.g. glucose (diabetes); cholesterol, fatty acids and triglycerides (hyperlipidemia) (atherosclerosis) (obesity). In one aspect, the invention is directed towards the use of the prodrugs to enhance oral drug delivery. In another aspect, the prodrugs are used to prolong pharmacodynamic half-life of the drug. In addition, the prodrug methodology of the current invention is used to achieve sustained delivery of the parent drug. In another aspect, the prodrugs are used to increase the therapeutic index of the drug. In another aspect of the invention, a method of making these prodrugs is described. In another aspect, the prodrugs are also useful in the delivery of diagnostic imaging agents to the liver.

  本发明涉及含醇、胺和硫醇的药物的新型环磷酸酯前药、其制备、合成中间体及其用途。发明的另一个方面是使用前药治疗从肝脏和类似组织和细胞中受益于增强药物分布的疾病，这些组织和细胞表达细胞色素P450，包括肝炎、癌症、肝纤维化、疟疾、其他病毒和寄生虫感染以及肝脏负责生化终产物的过度产生的代谢性疾病，例如葡萄糖（糖尿病）；胆固醇、脂肪酸和甘油三酯（高脂血症）（动脉粥样硬化）（肥胖症）。在一个方面，本发明涉及使用前药增强口服药物的传递。在另一个方面，前药用于延长药物的药效半衰期。此外，本发明的前药方法用于实现母药的持续释放。在另一个方面，前药用于增加药物的治疗指数。在本发明的另一个方面，还描述了一种制造这些前药的方法。在本发明的另一个方面，前药还可用于将诊断成像剂传递至肝脏。
• PRODRUGS FOR LIVER SPECIFIC DRUG DELIVERY
  申请人：Metabasis Therapeutics Inc.

  公开号：EP1210354A1

  公开（公告）日：2002-06-05
• US6752981B1
  申请人：——

  公开号：US6752981B1

  公开（公告）日：2004-06-22
• US7303739B2
  申请人：——

  公开号：US7303739B2

  公开（公告）日：2007-12-04