2-((3-fluorobenzyl)oxy)ethanol | 851859-50-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-((3-fluorobenzyl)oxy)ethanol
• 英文别名: 2-{[(3-fluorophenyl)methyl]oxy}ethanol；2-[(3-Fluorophenyl)methoxy]ethan-1-ol；2-[(3-fluorophenyl)methoxy]ethanol
• CAS: 851859-50-2
• 化学式: C₉H₁₁FO₂
• 分子量: 170.184
• InChiKey: QNTPWFDJZDQATN-UHFFFAOYSA-N

物化性质

• 沸点：
  252.7±20.0 °C(Predicted)
• 密度：
  1.158±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-((3-fluorobenzyl)oxy)ethanol 在 四溴化碳 、 盐酸羟胺 、 sodium hydride 、 三苯基膦 、 sodium iodide 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 28.0h， 生成
  参考文献：
  名称：

  Accessible Chiral Linker to Enhance Potency and Selectivity of Neuronal Nitric Oxide Synthase Inhibitors

  摘要：

  The three important mammalian isozymes of nitric oxide synthase (NOS) are neuronal NOS (nNOS), endothelial NOS (eNOS), and inducible NOS (iNOS). Inhibitors of nNOS show promise as treatments for neurodegenerative diseases. Eight easily synthesized compounds containing either one (20a,b) or two (9a-d; 15a,b) 2-amino-4-methylpyridine groups with a chiral pyrrolidine linker were designed as selective nNOS inhibitors. Inhibitor 9c is the best of these compounds, having a potency of 9.7 nM and dual selectivity of 693 and 295 against eNOS and iNOS, respectively. Crystal structures of nNOS complexed with either 9a or 9c show a double-headed binding mode, where each 2-aminopyridine headgroup interacts with either a nNOS active site Glu residue or a heme propionate. In addition, the pyrrolidine nitrogen of 9c contributes additional hydrogen bonds to the heme propionate, resulting in a unique binding orientation. In contrast, the lack of hydrogen bonds from the pyrrolidine of 9a to the heme propionate allows the inhibitor to adopt two different binding orientations. Both 9a and 9c bind to eNOS in a single-headed mode, which is the structural basis for the isozyme selectivity.

  DOI：

  10.1021/ml400381s
• 作为产物：
  描述：

  3-氟苄醇 在 ruthenium trichloride 、 sodium periodate 、 锂硼氢 、 三甲基氯硅烷 、 苄基三乙基氯化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 7.0h， 生成 2-((3-fluorobenzyl)oxy)ethanol
  参考文献：
  名称：

  Accessible Chiral Linker to Enhance Potency and Selectivity of Neuronal Nitric Oxide Synthase Inhibitors

  摘要：

  The three important mammalian isozymes of nitric oxide synthase (NOS) are neuronal NOS (nNOS), endothelial NOS (eNOS), and inducible NOS (iNOS). Inhibitors of nNOS show promise as treatments for neurodegenerative diseases. Eight easily synthesized compounds containing either one (20a,b) or two (9a-d; 15a,b) 2-amino-4-methylpyridine groups with a chiral pyrrolidine linker were designed as selective nNOS inhibitors. Inhibitor 9c is the best of these compounds, having a potency of 9.7 nM and dual selectivity of 693 and 295 against eNOS and iNOS, respectively. Crystal structures of nNOS complexed with either 9a or 9c show a double-headed binding mode, where each 2-aminopyridine headgroup interacts with either a nNOS active site Glu residue or a heme propionate. In addition, the pyrrolidine nitrogen of 9c contributes additional hydrogen bonds to the heme propionate, resulting in a unique binding orientation. In contrast, the lack of hydrogen bonds from the pyrrolidine of 9a to the heme propionate allows the inhibitor to adopt two different binding orientations. Both 9a and 9c bind to eNOS in a single-headed mode, which is the structural basis for the isozyme selectivity.

  DOI：

  10.1021/ml400381s

文献信息

• 3,4,5-Substituted piperidines as therapeutic compounds
  申请人：Herold Peter

  公开号：US20070167433A1

  公开（公告）日：2007-07-19

  Use of compounds of the general formula (I) and pharmaceutically acceptable salt thereof, in which R 1 , R 2 , R 3 , R 4 , W, X and Z, n and m have the definitions illustrated in detail in the description, as beta-secretase, cathepsin D, plasmepsin II and/or HIV protease inhibitors.

  在一般式（I）及其药用可接受盐中使用具有详细定义的R1、R2、R3、R4、W、X和Z、n和m的化合物，作为β-分泌酶、半胱氨酸蛋白酶D、质粒蛋白酶II和/或HIV蛋白酶抑制剂。
• Muscarinic acetylcholine receptor antagonists
  申请人：Laine I. Damane

  公开号：US20070185155A1

  公开（公告）日：2007-08-09

  Muscarinic Acetylcholine Receptor Antagonists and methods of using them are provided.

  提供了肌肽乙酰胆碱受体拮抗剂及其使用方法。
• Remote C(sp ³ )−H Acylation of Amides and Cascade Cyclization via N‐Heterocyclic Carbene Organocatalysis
  作者：Qing‐Zhu Li、Rong Zeng、Yang Fan、Yan‐Qing Liu、Ting Qi、Xiang Zhang、Jun‐Long Li

  DOI：10.1002/anie.202116629

  日期：2022.4.4

  An N-heterocyclic carbene catalyzed remote C(sp3)−H acylation of amides was developed, and also combined with a cascade cyclization. Over 120 functionalized δ-amino ketones and isoquinolinones with diverse substituents were synthesized in up to 99 % yield under mild conditions. Preliminary mechanistic investigations shed light on the organocatalytic radical reaction mechanism.

  开发了一种 N-杂环卡宾催化的酰胺的远程 C(sp 3 )-H 酰化，并结合了级联环化。在温和条件下以高达 99% 的产率合成了 120 多种具有不同取代基的功能化 δ-氨基酮和异喹啉酮。初步的机理研究揭示了有机催化自由基反应的机理。
• Muscarinic Acetylcholine Receptor Antagonists
  申请人：Laine Damane I.

  公开号：US20090124653A1

  公开（公告）日：2009-05-14

  Muscarinic Acetylcholine Receptor Antagonists and methods of using them are provided.

  本文提供了毒蕈碱乙酰胆碱受体拮抗剂及其使用方法。
• Piperidine Derivatives As Renin Inhibitor
  申请人：Herold Peter

  公开号：US20080076766A1

  公开（公告）日：2008-03-27

  The application relates to novel substituted piperidines of the general formula (I) in which R 1 , R 2 , R 3 , R 4 , W, X, Z, m and n are each as defined in detail in the description, to a process for their preparation and to the use of these compounds as medicines, in particular as renin inhibitors.

  该申请涉及一种新的取代哌啶，其通式为(I)，其中R1、R2、R3、R4、W、X、Z、m和n在详细说明中各自定义，以及其制备方法和这些化合物作为药物的用途，特别是作为肾素抑制剂。