dipentyl phosphorofluoridate | 625-21-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: dipentyl phosphorofluoridate
• 英文别名: phosphorofluoridic acid dipentyl ester；fluorophosphoric acid dipentyl ester；Fluorophosphorsaeure-dipentylester；Dipentyl-fluorophosphat；Phosphorsaeure-dipentylester-fluorid；Dipentoxyfluorophosphine oxide；1-[fluoro(pentoxy)phosphoryl]oxypentane
• CAS: 625-21-8
• 化学式: C₁₀H₂₂FO₃P
• 分子量: 240.255
• InChiKey: XUBIBVPNAIZAPL-UHFFFAOYSA-N

物化性质

• 沸点：
  143-144 °C(Press: 30 Torr)
• 密度：
  1.018±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  phosphonic acid dipentyl ester 在 potassium fluoride 、 tri-chlorocyanuric acid 作用下， 以 乙腈 为溶剂， 反应 0.58h， 以91%的产率得到dipentyl phosphorofluoridate
  参考文献：
  名称：

  Trichloroisocyanuric Acid–KF as an Efficient Reagent for One-Pot Synthesis of Dialkylfluorophosphates from Dialkylphosphites

  摘要：

  Trichloroisocyanuric acid-KF afforded dialkylfluorophosphates from dialkylphosphites at room temperature through a facile electrophilic-nucleophilic metathesis.

  DOI：

  10.1080/00397910802215880

文献信息

• Arylfluorophosphate Inhibitors of Intestinal Apical Membrane Sodium/Phosphate Co-Transport
  申请人：Peerce Brian

  公开号：US20130059822A1

  公开（公告）日：2013-03-07

  The present invention is directed to fluorophosphates, and pharmaceutical compositions thereof, which are inhibitors of intestinal apical sodium/phosphate co-transport and are useful in the treatment of hyperphosphatemia, in reducing blood phosphate levels, and in treating hypertension.

  本发明涉及氟磷酸盐及其制药组合物，它们是肠道顶端钠/磷共转运抑制剂，可用于治疗高磷血症，降低血磷水平，并用于治疗高血压。
• Voigt,D. et al., Bulletin de la Societe Chimique de France, 1969, p. 3383 - 3386
  作者：Voigt,D. et al.

  DOI：——

  日期：——
• Ethyl Octylphosphonofluoridate and Analogs: Optimized Inhibitors of Neuropathy Target Esterase
  作者：Shao-Yong Wu、John E. Casida

  DOI：10.1021/tx00050a011

  日期：1995.12

  The relation between organophosphorus-induced delayed neuropathy (OPIDN) and brain neuropathy target esterase (NTE) inhibition is further examined in hens by structure-activity studies leading to the most potent in vitro NTE inhibitors known, which are then examined for their neuropathic effects in vivo in hens. The principal compounds studied are alkyl alkylphosphonofluoridates and dialkyl phosphorofluoridates. Potencies that exceed those of any previous inhibitors under the standard in vitro NTE assay condition are achieved with alkyl octylphosphonofluoridates (ethyl, isopropyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, and 3-iodopropyl), 2-iodoethyl hexylphosphonofluoridate, and dialkyl phosphorofluoridates [ethyl, nonyl; di(2-iodoethyl); di(3-iodopropyl); dipentyl]. The concentration for 50% NTE inhibition (I-50) Of these compounds is 0.04-0.14 nM. Thirty-eight less active analogs including aryl phosphonates and aryl phosphates give I(50)s of 0.27-4730 nM. For highest potency the summation of length of the alkyl and alkoxy groups on phosphorus should be 12-16 atoms (carbons, oxygens, and phosphorus) (a terminal iodo substituent in this relationship is equivalent to a propyl group). In general, the phosphonofluoridates and phosphorofluoridates are more active than analogs with leaving groups other than fluorine, i.e., phenoxy, 4-nitrophenoxy, 4-cyanophenoxy, 3,4-dichlorophenoxy, and 4H-1,3,2-benzodioxaphosphorin. Considering the exceptional potencies of ethyl and 2-iodoethyl octylphosphonofluoridates (I50S of 0.04 and 0.09 nM, respectively), it is not surprising that at ip doses of 10-30 mg/kg they inhibit brain NTE by 82-97% 48 h after treatment. However, unexpectedly, only the ethyl but not the 2-iodoethyl compound induces OPIDN, possibly associated with the greater ease of aging for NTE inhibited with the ethyl than the 2-iodoethyl compound (as observed in vitro both spontaneously and on induction by potassium fluoride). The high potency of ethyl octylphosphonofluoridate and several analogs as NTE inhibitors suggests that they are useful probes in determining the toxicological features of this secondary lesion for organophosphorus poisoning.
• Dichlorodimethylhydantoin–KF as an efficient reagent for one pot synthesis of dialkylfluorophosphates from dialkylphosphites
  作者：A.K. Gupta、J. Acharya、D.K. Dubey、M.P. Kaushik

  DOI：10.1016/j.jfluchem.2007.11.008

  日期：2008.3

  Organic-inorganic hybrid reagent dichlorodimethylhydantoin - KF (DCDMH - KF) mixture was explored as an efficient reagent for the direct conversion of dialkylphosphites to their corresponding dialkylfluorophosphates at room temperature and in shorter reaction times through a facile electrophilic - nucleophilic metathesis. (c) 2007 Elsevier B.V. All rights reserved.
• Single step fluorination of dialkylphosphites: trichloroacetonitrile–KF as an efficient reagent for the synthesis of dialkyl fluorophosphates
  作者：A.K. Gupta、J. Acharya、D. Pardasani、D.K. Dubey

  DOI：10.1016/j.tetlet.2008.02.051

  日期：2008.3

  The use of trichloroacetonitrite and KF mixture is described as an efficient reagent for the direct conversion of dialkylphosphites to their corresponding dialkyl fluorophosphates via in situ formation of dialkyl chlorophosphates in one-pot. (C) 2008 Elsevier Ltd. All rights reserved.