3-氟二氢呋喃-2(3H)-酮 | 3885-31-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: 3-氟二氢呋喃-2(3H)-酮
• 英文名称: 2,3-dideoxy-2-fluoro-D,L-glycero-tetronolactone
• 英文别名: α-Fluoro-γ-butyrolactone；3-fluorodihydrofuran-2(3H)-one；3-fluoro-dihydro-furan-2-one；2-fluorobutyrolactone；α-Fluor-γ-butyrolacton；3-fluorooxolan-2-one
• CAS: 3885-31-2
• 化学式: C₄H₅FO₂
• 分子量: 104.081
• InChiKey: QSGGLAGTJDEIAN-UHFFFAOYSA-N

物化性质

• 沸点：
  86-88 °C(Press: 11 Torr)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-氟二氢呋喃-2(3H)-酮 在 氢溴酸 作用下， 以 乙醇 为溶剂， 以34%的产率得到ethyl 4-bromo-2-fluorobutanoate
  参考文献：
  名称：

  Derivatives of guanine for combating herpes virus infections

  摘要：

  该公式的新型抗病毒化合物为##STR1##其中R.sub.1和R.sub.2中的每一个，相同或不同，均为氢、羟基或氟；但是当R.sub.1和R.sub.2不同时，R.sub.1或R.sub.2为氢，当R.sub.1和R.sub.2相同时，R.sub.1和R.sub.2为羟基或氟；或其生理可接受的盐或其光学异构体，其制备方法，含有该化合物的药物制剂，以及用于治疗病毒感染和其他由病毒引起的疾病的方法。

  公开号：

  US04495190A1
• 作为产物：
  描述：

  (±)-α-羟基-γ-丁内酯 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以58%的产率得到3-氟二氢呋喃-2(3H)-酮
  参考文献：
  名称：

  Development of Fluorine-18 Labeled Metabolically Activated Tracers for Imaging of Drug Efflux Transporters with Positron Emission Tomography

  摘要：

  Increased activity of efflux transporters, e.g., P-glycoprotein (P-gp) and breast cancer resistance protein (BCRP), at the blood brain barrier is a pathological hallmark of many neurological diseases, and the resulting multiple drug resistance represents a major clinical challenge. Noninvasive imaging of transporter activity can help to clarify the underlying mechanisms of drug resistance and facilitate diagnosis, patient stratification, and treatment monitoring. We have developed a metabolically activated radiotracer for functional imaging of P-gp/BCRP activity with positron emission tomography (PET). In preclinical studies, the tracer showed excellent initial brain uptake and clean conversion to the desired metabolite, although at a sluggish rate. Blocking with P-gp/BCRP modulators led to increased levels of brain radioactivity; however, dynamic PET did not show differential clearance rates between treatment and control groups. Our results provide proof-of-concept for development of prodrug tracers for imaging of P- /BCRP function in vivo but also highlight some challenges associated with this strategy.

  DOI：

  10.1021/acs.jmedchem.5b00652

文献信息

• Power- and structure-variable fluorinating agents. The N-fluoropyridinium salt system
  作者：Teruo Umemoto、Shinji Fukami、Ginjiro Tomizawa、Kikuko Harasawa、Kosuke Kawada、Kyoichi Tomita

  DOI：10.1021/ja00179a047

  日期：1990.11

  N-Fluoropyridinium salts provide a new system of fluorinating agents by which a wide range of nucleophilic substrates differing in reactivity can be fluorinated due to the varying degree of fluorinating power and also fluorinated very selectively through structural alteration. The scope of selective fluorination should be broadened considerably on the basis of the present results. The N-fluoropyridinium

  N-氟吡啶鎓盐提供了一种新的氟化剂系统，通过该系统，由于氟化能力的不同程度，反应性不同的各种亲核底物可以被氟化，并且还可以通过结构改变非常有选择性地氟化。在现有结果的基础上，选择性氟化的范围应该大大拓宽。因此，N-氟吡啶鎓盐系统应该可以制备许多有用的有机氟化合物
• [EN] IRAK4 INHIBITING AGENTS<br/>[FR] AGENTS D'INHIBITION DE L'IRAK 4
  申请人：BIOGEN MA INC

  公开号：WO2016011390A8

  公开（公告）日：2016-04-07
• Selective, Electrophilic Fluorinations Using N-Fluoro-o-benzenedisulfonimide
  作者：Franklin A. Davis、Wei Han、Christopher K. Murphy

  DOI：10.1021/jo00120a014

  日期：1995.7

  The synthesis of N-fluoro-o-benzenedisulfonimide (NFOBS, 2) and its use as an ''electrophilic'' fluorinating reagent with nucleophilic substrates is described and compared with that of N-fluorobenzenesulfonimide (NFSi, 3). NFOBS (2) is prepared in three steps in 81% overall yield from commercially available o-benzenedisulfonic acid (4) and involves treatment of o-benzenedisulfonimide (6) with dilute fluorine (10% F-2/N-2). Reaction of 2 with metal enolates, silyl enol ethers, and 1,3-dicarbonyl compounds affords the corresponding alpha-fluoro compounds in yields up to 95%, with good control of mono- and difluorination. Fluorination of ortho-metalated aromatic compounds was achieved in modest to good yields (10-80%). While the reactivities of 2 and 3 are similar, better yields were observed with the former reagent in the fluorination of metal enolates, Grignard and lithium reagents, while 3 gave better results with the ortho-lithiated aromatic substrates. The available evidence suggests an S(N)2-type mechanism for the fluorination of nucleophilic substrates by these reagents.
• Preparation of .alpha.-fluorocarboxylic acids and derivatives
  作者：Suzanne T. Purrington、Daniel L. Woodard

  DOI：10.1021/jo00297a090

  日期：1990.5
• Syntheses of fluorinated ligands to probe binding of antigenic determinants of Vibrio cholerae O:1, serotypes Inaba and Ogawa, to antibodies
  作者：Alex H.C. Chang、Derek Horton、Pavol Kováč

  DOI：10.1016/s0957-4166(99)00505-4

  日期：2000.2

  Derivatives of methyl alpha-glycosides of antigenic determinants of Vibrio cholerae O:1, serotypes Inaba and Ogawa, specifically Fluorinated at position 2' or 4' have been synthesized by coupling the appropriately fluorinated derivatives of 3-deoxy-L-glycero-tetronic acid with the methyl oc-glycosides of perosamine. The compound having the fluorine atom at position 2 was obtained by electrophilic addition of fluorine to the glycal derived from the parent antigenic determinant, serotypes Inaba, using Selectfluor(TM) as a fluorination reagent. (C) 2000 Elsevier Science Ltd. All rights reserved.

表征谱图